On Bobby Fischer, the Greatest Chess Player of All Time

Epigraph:

Why not see a legend while it’s still being made?

The Silver Jews

Introduction:

This essay looks at the life and career of the greatest chess player of all time, Bobby Fischer.

This one is especially meaningful to me because my dad, Ross Thomas, taught me to play chess when I was a little kid. Neither of us has ever been a great player, but we both love the game. Ross still enjoys playing today as do I, and although I don’t follow competitive chess as closely as I once did, I’ve never lost my fascination with its history—or with the remarkable personalities who have shaped it.

Few personalities have ever been as brilliant, complicated, or tragic as Bobby Fischer.

In this essay I explore Fischer’s astonishing rise from Brooklyn prodigy to World Champion, the unforgettable 1972 Match of the Century against Boris Spassky, his extraordinary genius over the board, and the painful decline that followed. Like many towering figures, Fischer left behind a legacy that is impossible to separate from his contradictions.

Whether you’re a lifelong chess player or simply interested in remarkable lives, I hope you’ll enjoy the journey. As always, thank you for reading, commenting, sharing, and making these conversations possible.

I. Brooklyn

There are bogglers, and then there is Bobby Fischer.

History is littered with men who threw away fortunes, marriages, careers, and reputations. Every generation seems to produce a few gifted souls who wake up one morning, look at a perfectly good life, and decide to drive it into a ditch at seventy miles an hour. Howard Hughes belongs in that conversation. John McAfee as well. A handful of Roman emperors deserve honorable mention. But if I had to pick a patron saint of the truly bewildering decision, the gold medal still goes to Bobby Fischer.

Which makes the whole thing even stranger, because Bobby began as almost the opposite of a boggler. He was a skinny kid from Brooklyn who found a chessboard before he found the rest of the world and went on in short order to change the game forever.

I never saw Bobby Fischer play. By the time I was old enough to understand chess, he long gone. The World Championship in Reykjavík belonged to another era, and Bobby himself had already begun drifting into legend. I didn’t discover him through television or newspaper headlines. I discovered him through my father, who loved chess and spoke of Bobby the way baseball fans talk about Willie Mays or boxing fans talk about Muhammad Ali. Bobby wasn’t simply another grandmaster. Bobby was Bobby.

Even if you know almost nothing about chess, you’ve probably heard the name. That’s rare.

Most world champions become famous inside their sport. Bobby transcended the board entirely. For a brief moment in 1972, during the height of the Cold War, a chess player became one of the most recognizable people on the planet. He wasn’t just trying to beat Boris Spassky. Millions of people saw him as the lone American challenging decades of Soviet dominance in the game’s intellectual heartland.

He won.

And then… Well. This is where the boggling really begins.

II. Brooklyn & Chess

Every legend has to begin somewhere. Abraham Lincoln had the log cabin. Muhammad Ali had Louisville. Bob Dylan had Hibbing. Bobby Fischer had a small apartment in Brooklyn, a single mother, and a chessboard.

Not exactly the ingredients from which you would expect history to emerge.

Bobby wasn’t born into wealth or privilege. There was no grandmaster father waiting to pass down generations of chess wisdom. There was no Soviet state pouring unlimited resources into his development. There was just a skinny, bright kid who discovered a game that somehow made more sense to him than almost everything else around him.

The game never let him go.

Neither, apparently, did he ever let go of it.

I never saw Bobby Fischer play.

By the time I was old enough to understand what a chessboard even was, Bobby had already disappeared from competitive chess. I was born in 1974, just two years after Reykjavík, so I missed the whole thing. My Bobby wasn’t the Bobby of television broadcasts and newspaper headlines. My Bobby came secondhand through my father.

Dad loved chess.

He wasn’t a master by any stretch, but he loved the history, the personalities, and above all Bobby Fischer. Long before YouTube breakdowns, Twitch streams, and chess engines stronger than every human being who has ever lived, my father told me stories about this kid from Brooklyn who walked into a game the Soviet Union practically owned and somehow beat them anyway.

To a little kid, that sounded impossible.

And maybe that’s why Bobby has fascinated me ever since.

Not because I became a serious chess player—I didn’t. Not because I memorized openings or dreamed of becoming a grandmaster. I didn’t do that either. Bobby fascinated me because even before I knew the details, he already felt larger than life. Some people become famous. Others become myths. Bobby somehow managed to become both before he was thirty.

There’s another thing I like about Bobby. He wasn’t polished. He wasn’t exactly charming. He wasn’t selling anything.

He didn’t seem remotely interested in being a celebrity. If anything, fame looked like something that had happened to him against his will. He wanted to play chess. The rest of the world insisted on turning him into a symbol.

That’s a dangerous bargain. Especially for someone who already viewed the world with suspicion.

The irony, of course, is that the qualities that made Bobby great at chess were probably the same qualities that made ordinary life so difficult. Absolute concentration. Endless preparation. Refusing to accept conventional wisdom. Seeing threats and possibilities invisible to everyone else. Across sixty-four squares those qualities made him nearly unbeatable. Outside the chessboard, they often made life bewilderingly complicated.

The boy from Brooklyn had found the one place in the world where everything made perfect sense. The trouble began when he had to leave the board.

III. Bobby’s Rise

The funny thing about genius is that it rarely announces itself politely. It doesn’t knock on the door. It kicks the damn thing in.

By the time Bobby Fischer was in his early teens, the whispers had already begun. Chess players who had spent decades studying the game found themselves losing to a kid who wasn’t even old enough to drive. Adults who expected to teach him lessons instead received one themselves. Tournament after tournament, Bobby kept climbing until people slowly stopped asking whether he was unusually talented and began asking a much stranger question:

How good can one human being actually become?

That question haunted the chess world for the next decade.

Remember, this wasn’t today’s chess. There was no internet. No YouTube lectures. No databases containing millions of games. No engines instantly pointing out every mistake with the emotional warmth of a tax auditor. If you wanted to improve, you studied books until they fell apart. You replayed famous games by hand. You stared at positions for hours. Chess was slower, lonelier, and in many ways far more mysterious.

Bobby loved every minute of it.

Or perhaps “loved” isn’t the right word. He consumed it. The game became less a hobby than an ecosystem. Everything else seemed secondary. School. Friends. Ordinary teenage life. Those things existed somewhere off to the side while Bobby disappeared deeper into sixty-four squares.

That kind of obsession usually scares people. Sometimes it should. But every now and then history rewards it.

By the late 1960s Bobby wasn’t merely America’s best player. He had become the only serious obstacle standing between the Soviet Union and permanent ownership of the World Championship. For decades the Soviets had treated chess almost as a national project. They produced champion after champion with an efficiency that bordered on the industrial. To beat one Soviet grandmaster was impressive.

To beat all of them? That sounded ridiculous. Bobby apparently didn’t’ received the memo. What amazes me isn’t simply that he won. It’s how he won. He didn’t scrape through on lucky breaks. He didn’t sneak across the finish line. He flattened people.

Strong grandmasters—men who had dedicated their lives to becoming the best in the world—found themselves losing in ways that almost never happened at that level. His Candidates matches became the stuff of legend. The scores looked less like contests between equals than demonstrations of what happened when somebody operating on a different frequency sat down at the board.

There are athletes who win. There are athletes who dominate. Then there are the rare few who make everyone watching wonder whether the rules somehow stopped applying.

Babe Ruth. Wayne Gretzky. Michael Jordan. Michael Phelps. Usain Bolt. Bobby Fischer belongs in that conversation.

That’s the point people often miss. Bobby’s greatness wasn’t confined to chess enthusiasts. His rise had the unmistakable feeling of witnessing something unprecedented. You didn’t need to understand the Sicilian Defense or the King’s Indian to recognize that this skinny kid from Brooklyn was forcing an entire establishment to panic.

And somewhere along the way, Bobby stopped being just another chess player. He became a symbol. Americans wanted him to humble the Soviets. Journalists wanted a story. Television wanted a star. Sponsors wanted a celebrity. Everyone wanted a piece of Bobby Fischer. I’m not sure Bobby wanted any of them.

Looking back now, that’s the first place I can see the seeds of The Greatest Boggler beginning to sprout. Before the paranoia, before the disappearances, before the bizarre interviews and the years wandering from country to country, there was already a young man who seemed profoundly uncomfortable with everything that came attached to success except the game itself.

He wanted chess. The world insisted on giving him everything else. And history has a habit of charging interest on bargains like that.

IV. The Wooden Click

By the summer of 1972, Bobby Fischer had become something no chess player had ever really become before. A global celebrity. That sentence still sounds strange.

Golf has Tiger. Basketball has Jordan. Boxing has Ali. Baseball has Ruth. Tennis has Federer. Even if you’ve never watched them play, you know their names.

Chess? Chess wasn’t supposed to work that way.

Yet for a few extraordinary weeks in Reykjavík, Iceland, it did.

The Cold War had turned sixty-four squares into a battlefield. Bobby Fischer wasn’t simply challenging Boris Spassky for the World Championship. Fairly or unfairly, millions of people saw him as one American standing against an entire Soviet chess machine that had dominated the game for decades.

Every move became news. Every expression became news. Every delay became news. The entire world seemed to be watching a board covered in little carved pieces of wood. Most people would have loved every second of it. Bobby Fischer looked like he wanted to crawl under the table.

Here’s where “The Greatest Boggler” first begins to make sense. Most celebrities worry about bad reviews. Most athletes worry about losing.

Bobby worried about everything. The lights. The cameras. The spectators. The photographers. The chairs. The draft. The conditions. If there was a distraction available, Bobby could find it.

Reading about Reykjavík today, I can’t help but laugh at one recurring image. I picture Bobby sitting at the board convinced there were eyes in his soup. Not literally, of course, but psychologically. Somebody was always watching. Somebody was always listening. Somebody was always trying to gain an advantage.

The walls had ears. The soup had eyes. The room itself felt hostile. To the outside world, this looked ridiculous. To Bobby, I suspect, it felt completely real.

The most famous example has become almost comic. The noise. Specifically…

The little wooden click.

Imagine devoting your entire life to becoming the greatest chess player on Earth. You arrive for the biggest match in the history of the game. Billions of people—well, what feels like billions—are watching. Your opponent reaches for a knight. He places it on the board.

Click.

Bobby couldn’t stand it. Now, I admit, this is where my sympathy and my sense of humor collide. Part of me wants to put an arm around Bobby and say,

“Buddy… it’s a knight.”

“It’s made of wood.”

“It’s going to make a little wooden click.”

“It just is.”

“Have a cup of tea.”

“Take a breath.”

“Let’s play.”

Because the knight isn’t going to stop clicking. It just isn’t. The cameras aren’t going to disappear. The reporters aren’t going to go home. History has arrived. You’re Bobby Fischer. This is the price.

But another part of me wonders what that match must have felt like from inside Bobby’s own head.

Imagine carrying not only your own expectations but those of an entire country. Imagine believing every sound matters. Every movement matters. Every distraction matters. Imagine sitting across from the Soviet World Champion knowing that one lapse in concentration could cost you everything. Suddenly the little wooden click doesn’t seem quite so funny anymore.

It becomes symbolic. The click isn’t really about the knight. It’s about a mind that could never completely switch itself off. That’s Bobby.

The same obsessive concentration that allowed him to discover combinations invisible to everyone else also made ordinary imperfections almost unbearable. His gift and his burden may have been the very same thing. The remarkable thing is that none of it ultimately mattered.

Not the cameras. Not the click. Not the endless negotiations. Not the circus surrounding the match. Bobby won. Against all the noise, all the distractions, all the pressure, he became World Champion. For one shining moment, the kid from Brooklyn stood alone at the top of the chess world. It should have been the beginning of a long reign. Instead, astonishingly, it proved to be the beginning of something else entirely.

The greatest boggler had finally reached the summit. Now he was about to begin climbing back down.

V. The Walk Away

History loves a coronation. It has far less patience for an abdication.

If this were a Hollywood movie, Bobby Fischer wins the World Championship in Reykjavík, returns home a conquering hero, defends the title half a dozen times, writes a bestselling book, gives exhibitions around the world, settles into a comfortable house somewhere in California, and spends old age dispensing colorful stories to admiring grandchildren.

Instead… He walked away. Not immediately. Not dramatically. Just… steadily. Like a man fading into the California sun. That’s the image that stays with me. Not the young genius lifting the crown. The older Bobby, somewhere in Los Angeles, drifting farther and farther from the life everyone assumed he would lead.

People forget just how extraordinary this decision was. Imagine Michael Jordan retiring forever after his first NBA title. Imagine Tiger Woods winning the Masters once and never entering another major. Imagine Bob Dylan releasing Highway 61 Revisited and deciding he’d said everything he needed to say.

That’s the scale of Bobby’s disappearance. He simply stopped defending the thing he had spent his entire life trying to win.

Officially, there were disputes over match conditions, prize funds, and the rules proposed by FIDE. Bobby wanted changes. FIDE accepted some, rejected others, and when agreement couldn’t be reached, he refused to play. In 1975 the title passed to Anatoly Karpov by default.

No final game. No dramatic defeat. Just… Silence.

That, to me, is the first truly monumental boggle. Because Bobby had finally reached the summit. The hard part was over. History was his.

He could have defended the title once, twice, maybe five times. He could have become the elder statesman of American chess. He could have written books, taught children, appeared on television once a year, smiled for the cameras, and lived comfortably for the next forty years.

Instead he disappeared.

The farther Bobby drifted from chess, the farther he seemed to drift from almost everyone else. His relationship with his mother had always been complicated. She had encouraged his early interest in chess but also worried, understandably, that it was consuming his life.

As Bobby became more famous, the distance between them widened. Their relationship fractured, and by adulthood they were largely estranged. There is something deeply sad about that. The person who first helped place a chessboard in his life became someone increasingly absent from it.

Then came the paranoia. Now, I want to tread carefully here. It’s tempting to diagnose people after the fact. Every eccentric becomes “obviously” this or “clearly” that. Real life isn’t that tidy.

What we do know is that Bobby became increasingly distrustful of institutions, governments, journalists, organizers, and eventually whole groups of people. The suspicious streak that had surfaced during Reykjavík seemed to expand until almost nothing escaped it.

The cameras weren’t merely annoying. People weren’t merely mistaken. The soup still had eyes. Everywhere Bobby looked, somebody seemed to be watching. Somebody seemed to be cheating. Somebody seemed to be plotting.

And perhaps the saddest part is that the world kept giving him reasons to feel besieged. Fame invites attention. Attention attracts opportunists. The more Bobby withdrew, the more mysterious he became, and the more mysterious he became, the more people pursued him.

Round and round it went. By the 1980s, he had become almost a ghost.

There were periods when he was reportedly living with remarkably little money. Accounts differ on exactly how precarious his circumstances became, but there were stretches in Southern California when he moved from place to place, staying with acquaintances, in modest accommodations, sometimes even homeless, living a life almost unimaginable for the most famous chess player in the world.

That image boggles my mind. The undisputed World Champion. The man who had conquered the Soviet chess empire. A man without a stable home. How does that happen?

Then there is even a darker chapter. This is has to with Bobby’s antisemitic statements. There is no graceful way around them. They were ugly.

They became more frequent as he grew older, and they permanently damaged his reputation. The bitter irony, of course, is that Fischer had Jewish ancestry through his family background, making his rhetoric all the more bewildering. Whatever mixture of grievance, paranoia, anger, or ideology produced those statements, they caused real harm and deserve neither excuse nor romanticization.

This is where the essay stops being merely funny. Because up until now we’ve been laughing about wooden clicks. About photographers. About impossible demands. About eyes in his soup. Now we’re watching a genuine hero unravel in public. That’s different. It’s heartbreaking.

I keep coming back to the same question. What if Bobby had simply found peace?

Not perfection. Just peace. A little house. A morning walk. A cup of coffee. Chess club on Tuesdays. A few exhibitions every year. Maybe a family, maybe not. Just… enough.

Instead, the world champion kept walking. Farther from chess. Farther from home. Farther, it sometimes seemed, from himself.

And the California sun kept getting lower

VI. The Long Decline

There’s an old saying that every man dies twice. The first time is when his heart stops. The second is the last time someone says his name.

If that’s true, Bobby Fischer may never die.

Even people who couldn’t explain en passant or the Sicilian Defense know who Bobby Fischer was. The tragedy is that millions know him for the wrong reasons. The years after Reykjavík don’t unfold so much as scatter. He’s here. He’s there.

Budapest. The Philippines. Japan. Iceland. Anonymous apartments. Hotel rooms. Friends’ spare bedrooms. Long disappearances.

Then suddenly he’d surface again, as if he’d been underwater for years. The world would remember. Then he’d vanish once more. His life begins to feel almost impossible to narrate because it no longer has a center.

There’s no career. No family life to anchor the story. No steady work. No annual rhythm. Just movement. Always movement.

I’ve known people like that. Not world champions. Just drifters. Men who are always leaving. Always beginning again. Always convinced that the next city, the next apartment, the next job, the next relationship will finally outrun whatever has been chasing them.

It never does.

Because the thing following them is themselves. That’s Bobby’s sadness. No matter where he went, Bobby Fischer came too. There were occasional bursts of hope. Every few years somebody would announce that Bobby was coming back.

Maybe another match. Maybe another appearance. Maybe another interview. Maybe this time everything would settle down. It never quite happened.

Instead, Bobby became almost mythological. People told stories.

“I heard he’s living here…”

“I heard somebody saw him there…”

“I heard he’s working on this…”

Like Elvis or Howard Hughes, the man slowly disappeared while the legend continued multiplying.

The saddest thing about isolation is that eventually it becomes self-reinforcing. If you believe everyone is watching you you stop trusting people. When you stop trusting people you become lonely. Loneliness makes suspicion stronger. Suspicion creates more loneliness.

Round and round it goes. Eventually the circle becomes almost impossible to break. I don’t pretend to know exactly what was happening inside Bobby’s mind. None of us can. It’s easy—far too easy—to diagnose historical figures from the comfort of an armchair decades later.

Life isn’t a psychology textbook. Human beings rarely fit neatly into categories. What we can say is simpler.

Bobby became increasingly isolated. Increasingly angry. Increasingly suspicious. And increasingly difficult for the people who cared about him to reach.

Those are observations. They’re almost enough. The truly heartbreaking part is that flashes of the old Bobby never seemed to disappear. Whenever chess came up, the brilliance was still there. He could still see the board in ways almost nobody else could.

He advocated for Chess960, arguing that modern opening preparation had become too mechanical. Whether or not one agrees, it was another reminder that Bobby never stopped thinking deeply about the game itself. Even after decades away from the championship, his mind was still searching for new possibilities.

That fascinates me.

Because it suggests Bobby never really abandoned chess. He abandoned the world surrounding chess. Those are two very different things. People sometimes ask why geniuses so often end badly. I think that’s the wrong question.

Most geniuses don’t. Most extraordinarily gifted people build long, productive lives. The better question is why some geniuses seem unable to find a place to stand once the applause stops. For Bobby, victory solved the one problem he’d devoted his life to solving. After that…

What remains? You can spend twenty years climbing Everest. You can’t spend the next twenty standing on the summit. Eventually you have to come down. Most people descend into ordinary life. Bobby never really did.

He remained, psychologically, somewhere on that mountain. Still listening. Still watching. Still hearing the tiny wooden click. Still looking for eyes in his soup. And that’s why I keep resisting simple explanations. Was Bobby a hero?

Absolutely. Was he also capable of saying ugly, hateful, indefensible things? Absolutely. Both can be true. History isn’t obligated to give us clean characters. Some lives remain stubbornly contradictory. Perhaps that’s why Bobby still fascinates us more than fifty years after Reykjavík.

Not because he was perfect. Not because he was monstrous. Because he was profoundly, bewilderingly human. Gifted beyond measure. Flawed beyond measure. A man who could see twenty moves ahead on a chessboard and sometimes seemed unable to see the next move in his own life.

Then came one of my favorite Bobby stories.

For years, chess fans traded rumors that Bobby had quietly returned to the internet, anonymously playing blitz games against unsuspecting opponents. The greatest of those stories involved English grandmaster Nigel Short, who later said he believed he’d been playing Fischer himself.

Was it really Bobby? Nobody knows for certain. Maybe yes. Maybe no. That’s almost beside the point. The story sounds like Bobby, so I like to think that it is true.

The greatest chess player in history, hiding behind a screen name somewhere, refusing interviews, refusing publicity, refusing to tell anyone who he was, and simply playing chess because that was still the one language that made sense to him.

Whether it happened exactly that way almost doesn’t matter anymore. It has become mythology. And Bobby, by then, belonged as much to mythology as to history.

VII. Checkmate

Every story has to end somewhere. It’s fitting, I suppose, that Bobby Fischer’s ended in Iceland. Not New York. Not Brooklyn. Not Los Angeles. Not Moscow. Iceland.

The little island where, for one extraordinary summer in 1972, he became the most famous chess player who had ever lived. It was the only country that would still welcome him.

Life has a strange sense of symmetry. After years of drifting through countries and controversies, after the endless rumors, the disappearances, the interviews that shocked the world, the legal battles, the wandering, Iceland quietly opened its doors to him one last time.

In Iceland, at least, Bobby found something resembling peace. Not complete peace. I’m not sure Bobby Fischer was ever built for complete peace. But enough. Enough to walk. Enough to think. Enough to play a little chess. Enough, possibly, to grow old.

He did a couple of interviews just before his death and I have read one or two. In them he sounds, if not exactly becalmed, at least somewhere approaching peace. This is a good note to end on.

Bobby Fischer died in Reykjavik January 2008 at tixty-four years old. A chessboard has sixty-four squares. Just one of those funny coincidences I guess. It’s hard not to smile. The number somehow feels right. When Bobby died, the obituaries arrived almost immediately. Some celebrated the genius. Some dwelled on the paranoia. Some focused almost entirely on the antisemitism and the bitterness of his later years.

All of them were telling part of the truth. None of them were telling all of it.

That’s the difficulty with Bobby Fischer. He refuses to fit inside a headline. He wasn’t simply a genius. He wasn’t simply a crank. He wasn’t simply a hero. He wasn’t simply a tragic figure. He was all of those things. That’s what makes him so fascinating.

Earlier I called Bobby Fischer the greatest boggler who ever lived. I stand by it. Not because he was the strangest. History has produced stranger people.

Not because he was the cruelest. History has produced far crueler men.

But because no one ever stood so close to having everything and then walked away from so much of it.

That’s the boggle.

Not the wooden click. Not the cameras. Not the soup with eyes. Those were symptoms. The real mystery is simpler.

How does a boy from Brooklyn become the greatest chess player on Earth and never really find a place to live in the world outside the board?

I don’t know. I don’t think anyone does. Maybe that’s why we’re still talking about him. His chess itself is immortal. The combinations still sparkle. The games are still taught. The brilliancies are still breathtaking.

Young players who weren’t born until decades after Reykjavík still sit in quiet rooms and replay Bobby’s victories, shaking their heads at moves that seem impossible until suddenly they aren’t.

That’s one kind of immortality. The other is stranger. Some people leave behind answers. Bobby Fischer left behind questions.

Questions about genius. Questions about obsession. Questions about loneliness. Questions about the terrible price that brilliance sometimes demands.

Suppose Bobby Fischer were sitting across from us now. No cameras. No reporters. No photographers. No Soviet delegation. No championship. Just a quiet chess club on an ordinary Tuesday afternoon.

I’d like to think we’d set up the board. He’d reach for his knight. It would land with that tiny…

click.

I’d smile. He probably wouldn’t.

Then we’d play.

And for a little while at least, the world would make perfect sense again.

Dedication:

For Bobby. And for my dad, who taught me everything I know about chess. Dad you are my hero and I love you.

The Days and Nights of My 50s I: 7/20/26, the Unwritten Libretto.

Author’s Note:

Five days ago, I made what may prove to be the most important professional decision of my life.

For months—years really—I had been thinking about giving up my teaching career and becoming a full-time writer. I have talked to many of my family and friends about this and taken several small steps in this direction. I recently published a novel, have written and published hundreds of essays, and written almost every day for eighteen years. I have hundreds of pages of dream records, journals and letters, some sent and some only in draft form. I am hard at work on the sequel to my first novel, and am currently working on five books with many more in the making.

Over this time I have also become very good at making excuses. School is too busy. Life is complicated. The timing isn’t quite right. Next month. Next term. Next year. One day. It was all true, and yet it barely matters. A few days ago, I finally admitted what had been staring me in the face for a long time: if I wanted to call myself a writer, I had to stop waiting for someone else to make that decision for me. Whether I eventually succeed or fail is almost beside the point. The decision itself changed something in me. I stopped thinking about the life I wished I had and started taking responsibility for the one I actually have.

Today wasn’t the happiest day of my life, nor the saddest. It wasn’t the day I got married, the day my son was born, the day I published my first book, or the day I realized my marriage was ending. Objectively speaking, it was an ordinary Monday in Osaka. I listened to music. I wandered the city. I shared dinner and my bed with a woman whose path happened to cross mine for a couple of hours before diverging forever. By tomorrow morning she would be somewhere else, and so would I. Yet somewhere between checking into a modest hotel, thinking about my future, and sitting alone quietly after she left, something finally clicked. My teaching career is rapidly coming to a close. The marriage that defined most of my adult life is over. The books I dream about haven’t been written yet. The cities I may someday call home are still only possibilities. The people who will matter most over the next twenty years are, at this moment, complete strangers.

For the first time since I was a young man, there is no obvious script. That realization is exhilarating. It is also terrifying. Most of all, it is deeply liberating.

So this seems as good a place as any to begin this series.

Epigraph:

Yesterday is history. Tomorrow is a mystery.

Anonymous

Anything could happen.

Bash and Pop

I: My General Situation As of Today

For the better part of thirty years, my life had possessed a remarkable amount of structure. I graduated from college. I moved to Japan. I found a teaching career almost by accident and stuck with it for a quarter of a century. I got married, and my wife and I bought a house together in Kyoto. We raised a wonderful son together who we both love more than words can say. We have paid bills, argued over groceries, worried about our dear dog Daisy, taken vacations when we could afford to, and slowly accumulated the ordinary rituals that eventually become a life. There were wonderful years and there were difficult ones, but there was almost always a next step waiting patiently in front of me. Whether I liked the script or not, there was a some kind of a script.

Then, almost imperceptibly at first, it disappeared.

My marriage ended not with a single dramatic explosion but with the gradual realization that two decent people could simply reach the end of the road together. My teaching career, once the defining feature of my adult identity, began to quietly recede into the background. Friends scattered across countries and continents. My parents grew older. I turned fifty-two without feeling especially old, but with the unmistakable sense that I had entered the second half of whatever story remained.

It is a peculiar thing to discover that freedom and uncertainty are twins. For years I imagined freedom as something uncomplicated. Finish work. Write books. Travel. Meet interesting people. Drink coffee in strange cities. Listen to music until two in the morning. Wake up whenever I pleased. Answer to no one.

There is truth in that fantasy. There is another truth as well.

Freedom also means that no one hands you tomorrow. No institution is waiting to promote you. No family obligation automatically determines your next decision. No invisible current carries you downstream. Every meaningful choice becomes your responsibility. Every success belongs to you. Every failure belongs to you too.

That realization can feel less like opening a door than standing on the edge of a cliff. You can step forward. Or you can spend the rest of your life admiring the view. Five days before the evening you’re about to read about, I decided I was done standing still.

I wasn’t retiring, not yet anyway. I wasn’t exactly reinventing myself. I wasn’t chasing some impossible dream. I was simply acknowledging something that had probably been true for twenty years. I am a writer. I feel like I was born to be one. Whether anyone else eventually agrees is, in many ways, beside the point. The work itself has become the destination. Everything else—the cities, the books, the women, the music, the bars, the victories, the humiliations, the friendships, the failures—is simply material for my work.

This series is an attempt to pay attention to the contours of my daily life, in whatever form the may take. And, perhaps for the first time in my life, to trust that the story doesn’t need an outline before it begins.

II: Osaka

Osaka has always felt different to me than Kyoto.

Kyoto is the city where I built my adult life. It is where I have worked, and lived for more than twenty years with my life and son. It is where the mortgage was paid and our dog was walked, where ordinary afternoons quietly accumulated slowly into decades. I know its rhythms inside and out. I know which coffee shops open early, which bridges are worth crossing at sunset, and where to stand beside the Kamogawa when I need to remember that almost everything eventually passes.

Osaka has always been to me something else entirely.

It has never asked me to be responsible. When I come here, I feel somehow lighter. Less like a teacher. Less like a husband. Less like the man who spent twenty-four years inside the same corporate institution. Osaka has always given me permission to become, if only for a day or two, a slightly different version of myself. Not a better man or a worse one. Just someone with fewer expectations resting on his shoulders.

Perhaps every city we visit has a role to play in our lives. Kyoto has been my home. Tokyo has often been a dream. Singapore has long been my favorite escape. Osaka, though, has become my intermission. A place where I can step off the stage for a little while before the next act begins. A place to just get away.

This Monday afternoon I checked into a small APA Hotel not far from Shinsaibashi Station, which I affectionally call Mr. Shin. Like most APA hotels, it is clean, efficient, and just a little too compact. The room isn’t exactly designed for lingering. It is designed for sleeping, showering, and moving on. My suitcase for neatly against one wall. The desk is barely large enough for my laptop and a cup of coffee. The large television in front of my bed I will barely use. It suits my current mood perfectly.

I took a taxi to the hotel from Shin-Osaka Station and arrived around 7:30 PM. I dropped my overnight bag on the floor, drew the curtains apart, and looked out over another slice of Osaka. Nothing spectacular. Just traffic, apartment buildings, and the quiet machinery of a city getting on with its day.

I remember thinking how strange it felt to have absolutely nowhere I needed to be. No lesson to prepare. No meeting to attend. No papers to grade. No one waiting for me at all.

That realization no longer frightened me the way it once might have. It felt… spacious. There are moments in life when freedom announces itself with fireworks. This wasn’t one of them. It arrived almost silently. Like an empty afternoon. Like a city that has never asked me to explain myself. My hotel room is simple. It is what I can afford.

Outside, Osaka continued exactly as it always had. Inside, almost without me realizing it, the next stage of my life had already begun.

III: Meeting Yuki

I should flash back briefly here to introduce my date for the evening. There are evenings that require months of planning. This was not one of them.

The plan, such as it was, consisted of very little. Conversation. Sex. Cigarettes. Dinner. That was enough. As I stepped out of the taxi, I saw her standing quietly on the street.

She was slightly built, dressed in a simple black skirt, and carried herself with the quiet confidence of someone accustomed to meeting complete strangers. There was no dramatic meeting, no cinematic slow motion, no instant thunderbolt. We smiled, introduced ourselves, and within a minute or two were walking side by side into the hotel through the warm Osaka evening as though we had agreed to meet as old friends rather than someone we had never laid eyes on before.

Her name was Yuki.

We went up to my room and made the sort of awkward conversation that strangers always make at first. Where are you from? Where do you live today? Had I been to Osaka often? Was I enjoying the summer?

Nothing remarkable. Which, in retrospect, was itself remarkable. There is something deeply comforting about ordinary conversation. For a little while, neither of us had to be anything more than two people just getting to know each other.

Eventually, because pretending otherwise would have been absurd, the reason we had met entered the conversation. She is thirty-six and works as an escort. I had hired her for the evening.

There is no point dressing those facts up in prettier language. They are neither the whole story nor something I feel any particular need to defend. They simply belong to it. Human lives are untidy. We make decisions for reasons that are sometimes noble, sometimes lonely, sometimes curious, and sometimes impossible even to explain to ourselves. This was one of mine.

I went into the bathroom to wash up, took my clothes off, and hung them neatly on the hangers on the wall. By the time I came out of the bathroom she was naked too. That was what we were there for. I put on one of my favorite bands Whiskeytown, lay back on the bed for a few minutes, listened hard, and let the sweet sweet sounds of Ryan Adams’ voice wash over me. I was, briefly, in heaven.

Then, inevitably, we began to kiss. She is a smoker and tasted like stale tobacco and faintly like green peas. I am a smoker too so I am sure I tasted the same. She unwrapped one of the condoms that I had bought earlier for occasions just like this and began to pleasure me with her mouth. While I do enjoy oral sex to some extent, it is far from my favorite sexual act and I have never been able to cum this way. Not for lack of trying, I simply find that the women who have performed the act on me can never sufficiently been able to get their teeth out of the way. It is not their fault at all, but it is just that simple.

Soon enough, I asked her to climb on top of me. My penis was already erect and she was slick as well, and I entered her cleanly and easily. After a little while, we flipped around and began to engage in the missionary position. I was on the urge of cumming when I pulled out, turned over on my back, and finished my self off with two hands. Nine times out of ten I finish this way if I finish at all. After all, I know my own equipment better than else, so to speak. Before we began to have sex I put on some porn. I chose very quickly as we were on the clock. I selected some perfectly nun priest porn, totally chalk. Of course we both barely watched it as our eyes were mostly closed. The moment I came I toweled off, shut off the porn, and immediately pressed play on the Whiskeytown video I had paused before sex.

Then a funny thing happened. During sex she had repeatedly asked me to turn down the porn and to shush in general. She said we were at a business hotel and that we were bothering the other guests. Although I love to be babied. I do not like to mothered at all. It is just not my thing, and I have written about this at some length here. I already knew that I would not book Yuki again, and this moment helped crystalize my decision. She is sweet and cool, and I am glad I met her for one night, however she is just not my jam.

Anyway, she asked me to turn my music down. I just laughed and cranked it. Then she laughed too and the mood lifted and passed. Neither of us was yet in the mood for a shower, mostly because we were on the clock and by this point only had about 40 minutes left in our appointment. I did not feel like a round two, so I suggested we head down to the street to smoke for a smoke and then get a little dinner. Although we had less than an hour left and the hotel restaurant was a little busy, she agreed to have dinner with me.

We finished our cigarette and entered the first floor hotel restaurant. We sat down and briefly consulted the menu. The restaurant specializes in pasta, so I ordered tomato pasta with eggplant and she ordered the zucchini linguine. The food took a while to arrive, so halfway through the meal she asked for a doggie bag. I quickly finished my meal and we went upstairs so she could pack her bag.

The evening had never pretended to be anything it wasn’t. Neither of us confused it with romance. Neither of us imagined it was the beginning of some extraordinary love story. It was simply two lives crossing for a few hours before continuing in different directions. There is something quietly beautiful about that too.

Outside, Osaka was still very much alive. Trains rattled somewhere in the distance. Traffic rolled steadily beneath the hotel windows. Thousands of strangers were beginning nights that had nothing to do with ours. Ours, quietly and without complaint, was coming to an end.

I told her I was going to wash up for a minute. She said through the door that she had to leave. I said goodbye babes and she replied in the same fashion. When I came back out, she was already gone.

And I didn’t even kiss her goodbye.

IV: Coda

For most of my adult life, my future had always arrived with an outline. There was always another semester to teach. Another report to write. Another mortgage payment to make. Another family holiday to plan. Another school year waiting just over the horizon. Even when life became difficult, I almost always had a sense of what would come next. The details may change, but the broad shape of the story had already been sketched.

And now it hadn’t.

As I write this the marriage that defined nearly half my life has come to an end. My teaching career, after almost thirty years, is slowly coming to an end. My son is a grown man, trying his best making his own way in the world and earning his own money. My wife and I are immensely proud of him as well we should be. Our house of 19 years will soon belong to someone else. My life is rapidly becoming quite different and everything that had once seemed permanent has become part of the past.

This all may sound just a bit sad. Some of it may be, sure. It also happens to be exhilarating. Tomorrow I might wake up in Kyoto. Next month I might find myself in Singapore. A year from now I may be living in Osaka. Anything could happen.

Perhaps I’ll write ten more books. Perhaps no one will read them. Perhaps I’ll fall in love again. Perhaps I won’t. There will be close friends I haven’t made yet. There are cities I have not yet wandered. There are songs I haven’t fallen in love with, thank god.

There are mistakes waiting patiently for me. There are joys I cannot yet possibly imagine. For the first time since I was in my early twenties, the next chapter of my life has not yet been written.

As I stood there in that little Osaka hotel room, listening to Whiskeytown waft through the room, I finally understood what life had trying to tell me for days.

My life hadn’t fallen apart. It had, in fact, opened up. And somewhere beyond everything I thought I knew, waiting patiently for me, was the unfinished libretto.

Dedication:

For Yuki. Thanks for a lovely evening. I’ll never see you again, babe. Go with God.

On Why My Friend Litz and I Are No Longer Boyfriend and Girlfriend—for Now

Epigraph:

Some people claim there’s a woman to blame but I know it’s my own damn fault.
—Jimmy Buffett, “Margaritaville”

I. Meeting Litz Online

I met Litz on Tinder right around the end of April 2026, just about two and a half months ago today. Relationships often begin before either person realizes that anything has begun. Two strangers exchange a few messages, one of them sends a photograph or a joke, and suddenly an event that seemed inconsequential at the time becomes the first scene in a story.

Within a few days, Tinder suspended my account after yet another unsuccessful attempt to satisfy its increasingly byzantine photographic-identification system. I had failed this test many times before. The platform’s technology remained unable to determine that the large, slightly tired-looking man holding the phone was the same large, slightly tired-looking man depicted in the photographs directly beneath him. I found this highly frustrating, although by then it hardly mattered. Litz and I had already begun speaking elsewhere.

The first thing she sent me was a voice message. It lasted only a few seconds. I believe she simply introduced herself. What I remember best is her voice: low, warm, and unexpectedly musical. Litz had once been a professional singer. In her early twenties, she had received a recording contract in South Korea despite speaking little or no Korean at the time. I still do not entirely understand how that arrangement came about, but after hearing her speak I understood why someone might have wanted to record her.

Her voice reminded me slightly of Margo Timmins of Cowboy Junkies—not because they sounded identical, but because both possessed a quality that is difficult to manufacture: intimacy without effort and deeply sensual. To be frank, her voice turned me on immediately, and almost as quickly she did too. Litz could make a routine greeting sound private. Even when she was discussing work, groceries, family obligations, or the weather in Kochi City, I sometimes had the feeling that she was singing under her breath.

I told her how much I loved her voice. She later told me that she had fallen for me almost immediately. I cannot honestly say that I proceeded with greater caution.

Over the next six weeks, we talked almost every day, usually several times a day. Some calls lasted twenty minutes. Others lasted an hour, two hours, or longer. There were mornings when we spoke shortly after waking, afternoons when one of us called while walking somewhere, and nights when we continued talking long after both of us had run out of any practical reason to remain awake. By the time we met in person, we had accumulated hundreds of hours of conversation.

We discussed our families, our marriages, our children, our work, our financial worries, our health, our failures, and our hopes for whatever remained of the future. I have one adult son; she has two adult children. We spoke about the different paths that had carried us into our early fifties and about the lives we might still construct from there. We talked about music, food, travel, friendship, jealousy, loneliness, and sex. We also talked about nothing at all, which may be the greater test of intimacy. It is relatively easy to tell another person the dramatic events of one’s life. It is harder to remain interested while that person describes a difficult customer, a delayed train, an irritating piece of paperwork, or what she intends to eat for dinner.

With Litz, those ordinary conversations rarely felt ordinary.

At the time, I was emerging from a marriage that had lasted twenty-nine years. My wife and I had mutually decided to divorce earlier that spring, although the practical and emotional consequences of that decision were still unfolding. I had not lived as a single man since my early twenties. I had almost no recent experience of dating and even less understanding of how quickly two people could create a private world through their phones.

My mother and several other people cautioned me that Litz and I might be moving too fast. They were not hostile to her, nor were they trying to discourage me from beginning a new life. They had simply lived long enough to recognize acceleration when they saw it.

In retrospect, they were right.

At the time, however, the speed felt less like recklessness than recognition. After so many years inside one relationship, I mistook the intensity of discovery for certainty. Litz and I had not yet confronted the thousand small realities that distinguish knowing someone from imagining that one knows her. We knew one another’s histories, preferences, fears, and fantasies. We knew how to make each other laugh. We knew when the other person sounded tired or distracted. We knew which subjects produced excitement and which could quietly darken the mood.

That felt like knowledge. Some of it was. Some of it was projection. We also became virtually intimate before meeting in person. We had phone sex only twice, although the number is less important than what the experiences represented. Both of us had been lonely, and the intimacy provided a necessary outlet and a sense of closeness across a considerable distance.

At other times, when her work schedule or my obligations made a longer encounter impossible, we exchanged photographs or allowed each other brief intimate glimpses through the phone.

I do not include this information to be provocative. It matters because the relationship did not begin as a cautious friendship that slowly became romantic after a series of conventional dates. Emotionally and sexually, we had already moved far beyond introduction before we occupied the same room. By the time I traveled to Kochi, we had created expectations that neither of us fully understood.

For most of those six weeks, we had almost no disagreements. Litz sometimes expressed concern about whether I brushed my teeth frequently enough, an impressive question given that she was hundreds or thousands of kilometers away and had never stood close enough to inspect them. I assured her that I did. She remained unconvinced. This should perhaps have told us something.

Mostly, though, we were happy. We called each other baby. We spoke openly about becoming engaged and, eventually, getting married. We discussed travel plans and imagined a shared domestic future with the confidence available only to people who have not yet attempted to share a bathroom, a schedule, a kitchen, or a narrow futon.

I knew we were rushing. I rushed anyway.

I returned to Japan on June 12, two days before my fifty-second birthday. Almost immediately, I began arranging the trip to Kochi. Traveling there from Kyoto or Osaka is neither impossible nor particularly convenient. The round trip cost roughly ¥25,000, and the journey consumed much of a day. At fifty-two, a man should perhaps think carefully before spending that amount of time and money to meet someone he knows primarily as a voice emerging from a small electronic device. I went nonetheless.

By the time I reached Kochi Station, it was close to eleven at night. The late arrival eliminated any possibility of a proper birthday dinner. We bought snacks and wine instead and carried them back to a hotel near the station, where we did our best to turn convenience-store provisions into a meal.

There was an unavoidable strangeness in seeing her at full human scale. For six weeks she had existed inside photographs and rectangles, her face appearing or disappearing according to the strength of the connection. Now she was standing beside me, very small and entirely real. Litz is only four feet eleven inches tall. I am six feet three. The physical contrast between us was nearly comic, although neither of us seemed troubled by it.

We talked, drank wine, ate our improvised dinner, and gradually adjusted to the fact that the person we had imagined was now close enough to touch. The transition was easier than it might have been. Her voice was the same voice. Her humor survived the journey out of the phone. The affection between us did not vanish under the brighter and less forgiving light of an actual room.

We slept together that night and again the following morning. The sex was very good, but what mattered more was the sense of confirmation surrounding it. Whatever else we had misunderstood, the attraction was real. We were comfortable enough to laugh, to pause, and to begin again. Nothing felt forced. The night seemed to promise that the emotional and virtual intimacy of the previous six weeks could become an ordinary physical life.

Had the visit ended the following morning, I might have returned home convinced that we had been right about everything.

But eight hours together seemed inadequate after six weeks of anticipation and a ¥25,000 journey. Litz had an apartment in Kochi City, and I asked whether I might stay with her for a few days. She kindly agreed and began rearranging her work schedule so that we could spend more time together. I was, and remain, deeply grateful for that generosity. Inviting someone into a small home is an act of trust. Inviting a new boyfriend who is more than a foot taller than you and has arrived carrying the accumulated habits of twenty-nine years of marriage may be an act of courage.

I expected to remain for several days.

I stayed for ten.

For the first time, Litz and I would no longer be two people describing our daily lives from a distance. We would have a daily life together. We would wake in the same room, eat the same food, negotiate the same space, and discover whether the ease of our conversations could survive the pressures of proximity.

For the first few days, it did.

II. On Learning Someone in Person

By the end of my stay, I had remained in Kochi for about ten days.

Those ten days contained enough happiness to convince me that our relationship had real promise. They also contained enough friction to suggest that promise alone would not be enough.

Very quickly we settled into something resembling a small domestic partnership. Litz would go to work, though she had generously arranged her schedule so we could spend much more time together than originally planned. I cooked when I could, helped with the laundry, cleaned the apartment, ran errands, and generally tried to make myself useful. In the evenings we wandered around Kochi, stopped for drinks, browsed little shops, cooked simple meals together, and continued discovering one another in the quiet rhythm of ordinary life.

Those ordinary moments are, after all, where real relationships actually live. The first few days were wonderful. Then, almost imperceptibly, small tensions began to appear. The first involved something so minor that I still find it difficult to believe it became an issue at all.

I am a smoker. Rather than smoke inside Litz’s apartment, I stepped onto her small balcony several times a day. While smoking I would occasionally call my family or a close friend back in Kyoto. I was speaking quietly, during the daytime, on private property. To me it seemed entirely unremarkable.

Apparently one of Litz’s elderly neighbors felt otherwise.

The neighbor contacted the building management company and complained that the foreign guest next door was smoking and talking on the balcony. The management company called Litz and politely asked if her guest could simply take phone calls inside the apartment instead. That was all.

There was no threat of eviction. There was no confrontation. Nobody came to the apartment. No police appeared. No lease violations were mentioned. It was, from everything I could tell, a routine request that could have been solved in approximately thirty seconds.

I would gladly have stopped taking calls on the balcony. Instead, something else happened. Litz panicked.

When she told me about the call she was visibly shaken. She was close to tears. She repeatedly told me she might lose the apartment she had worked so hard to obtain. She imagined herself forced to leave. She imagined financial disaster. She imagined the worst possible outcome almost immediately.

I asked her a simple question.

“Baby, did the management company actually say you were going to be evicted?”

“No.”

“What did they say?”

“They asked that you talk on the phone inside.”

“I can absolutely do that.”

For me, the problem was already solved. For her, it had barely begun.

Looking back now, I understand that this was not really about balconies, cigarettes, or phone calls. It was anxiety. Real anxiety.Not theatrical anxiety. Not attention-seeking anxiety. Genuine anxiety that transformed relatively ordinary inconveniences into looming catastrophes.

I had not fully understood the depth of that tendency while we were talking online because online relationships naturally allow each person to present a calmer, more edited version of themselves. Daily life removes that luxury.

Unfortunately, her anxiety had an unfortunate side effect. It triggered my own. There are many unpleasant emotions in life, but few I dislike more than chronic stress. I can handle sadness. I can handle disappointment. I can even handle uncertainty reasonably well. Constant anxiety, however, is simply not good for me.

As Litz became more anxious, I found myself becoming more anxious in return. Neither of us wanted that. Neither of us knew quite what to do about it.

Other small disagreements gradually appeared. From my perspective they were simply the kinds of adjustments every new couple eventually faces. From her perspective they often carried greater emotional weight than I expected.

For example, she became increasingly interested in my daily routines.

How many times was I brushing my teeth? Why had I skipped shaving that morning? Was I taking proper care of myself?

These were perfectly reasonable questions in another context. Had we been married for twenty years, they might have seemed almost affectionate. But we were not married. We were not engaged. We had only recently met in person after knowing one another online.

I was fifty-two years old. She was in her fifties as well. I thought that certain decisions about my grooming, my appearance, and my daily habits still belonged primarily to me. I tried to explain this as gently as I could, just as she tried to explain why these matters genuinely concerned her.

Neither of us was entirely wrong. We were simply beginning to discover the practical differences between two people who had fallen in love through conversation and two people attempting to share everyday life. The gap continued to grow.

Reflecting on our first six weeks together, I am increasingly struck by something that I already knew to some extent. There is, in fact, a tremendous difference between getting to know somebody online and getting to know them in person. This may seem obvious. However, my time with Litz underscored that truth in ways I genuinely did not expect.

By the time I finally left Kochi, we were still together. We were still affectionate. We were still physically intimate. We still considered ourselves boyfriend and girlfriend. But beneath the surface, the first fault lines had begun to appear.


III. One Day at a Time

When people hear that a relationship has ended, they almost always want a simple explanation. Someone must have been the villain. Someone must have made the cheated. Someone must have loved less, cared less, tried less, or failed more spectacularly than the other. Real life rarely works that way in my experience.

Litz is one of the kindest people I have ever met. She is generous with her time, devoted to her children, remarkably hardworking, and capable of great tenderness. She also struggles with anxiety in ways that sometimes make ordinary life much harder than it needs to be. I, meanwhile, have my own collection of flaws. I rush into things. I value independence almost to a fault. I can be stubborn, dismissive of worries that seem obvious to others, and too quick to believe that every problem has a quick solution. These qualities have served me well in some areas of my life. In this relationship they sometimes made matters worse.

Neither of us was trying to hurt the other. We were simply carrying different histories into the same room. And perhaps that is what every relationship really is: two biographies attempting to occupy the same present tense. Sometimes they fit together naturally. Sometimes they require patience neither person yet possesses. Sometimes they arrive at exactly the wrong moment, even when the feelings themselves are genuine.

I do not regret meeting Litz. I do not regret falling in love with her. I certainly do not regret the laughter, the conversations that lasted until sunrise, the train rides, her little apartment in Kochi, or the quiet mornings when, for a little while at least, building a future together felt entirely possible. Those moments were real. They remain real.

Today, Litz and I are no longer boyfriend and girlfriend. We are, however, still good friends. We continue to care about one another and talk on the phone, and we both hope that time will provide perspective where emotion sometimes could not. We are discussing the possibility of traveling abroad together later this year. If this happens it happens and if it does not it does not. In either case, we will travel as friends, not as a couple.

The challenges in our relationship were the product of two imperfect people, each bringing old habits, old fears, old hopes, and old wounds into something new. That is not failure. It is simply the complicated business of being human.

So I will keep trying. To become a better man. A better friend. And, if circumstances ever allow, a better boyfriend. I hope Litz finds the same peace she has always wished for me.

Some people claim that there’s a woman to blame. But I know it’s my own damn fault. Perhaps.

Dedication:

For my friend Litz. Let’s just take things one day at a time, baby.

Note: Interested readers may also wish to read the love poem I wrote for Litz during the early part of our relationship. This poem is linked below.

On Meeting My Wife Sachie

Epigraph

Lisa says on a night like this it’d be so nice if you gave me a kiss.

—The Velvet Underground

Author’s Note: This essay is the first of several essays on the theme of my 27 year marriage to and recent divorce from my wife Sachie. As noted below, I met her in the summer of 1997 in Kumamoto Japan, her home town. I had just accepted a job with NOVA Corporation in that same city. This essay traces the first few months of our relationship.

The dates in this essay are reconstructed from memory nearly thirty years later. While I have tried to be as accurate as possible, the chronology is necessarily approximate.

Introduction:

In January of 1997, a few months before I departed for Japan, my grandfather Bill Kolb handed me an envelope.

Inside was $1,700 in cash.

Even now this sentence doesn’t sound quite real.

My mother still can’t believe it. Truth be told, neither can I. Bill wasn’t a wealthy man handing me money because he had too much of it. He simply believed in me. I don’t know exactly why. I was twenty-two years old, fresh out of college, without much of a plan beyond teaching English for a year somewhere on the other side of the world.

“Go with God,” he said. “Good luck in Japan.”

Nearly thirty years later, I still believe it was one of the greatest gifts anyone has ever given me.

Kumamoto and NOVA:

I left for Japan in April with two duffel bags, a stack of CDs, a handful of books, several pack of cigarettes, and the sort of confidence that belongs almost exclusively to young people. I wasn’t fearless. I was simply too young to appreciate all the things that could go wrong.

Before arriving in Kumamoto, NOVA sent me to Osaka for about a week of training. Most of the details have faded into that blur reserved for airports, orientation sessions, and hotel conference rooms, but I do remember how Japan felt.

Little things amazed. The stations. The food. The language. Even the convenience stores. I’d never been anywhere remotely like it.

Then I took the train south to Kumamoto.

People who have never been to Japan often imagine Tokyo whenever they hear the word “Japan.” Kumamoto is not Tokyo. It moves at its own pace. The downtown area is was built around a long covered shopping street—the Shotengai—that functioned as the city’s living room. People shopped there, met friends there, drank there, wandered there, and, if you stayed long enough, discovered that everybody seemed to know everybody else.

I arrived without knowing a soul. That didn’t last very long.

NOVA occupied a building at the north end of the Shotengai. At the time it was an enormous company, hiring English teachers from Britain, Australia, New Zealand, Canada and the United States. It has since gone downhill. The classrooms had glass walls. Lessons ran almost continuously. Teachers appeared, disappeared, smiled, taught, smiled again, and hurried off to the next class. It all worked surprisingly well.

It also felt a little like living inside an aquarium.

Things became even more interesting when I learned I’d be sharing an apartment with one of my supervisors.

Her name was Sam. She was from Wales, probably in her mid-thirties, and had an almost supernatural awareness of everybody else’s business. She wasn’t mean about it. She simply seemed constitutionally incapable of not knowing who was dating whom, who had called in sick, who had stayed out too late, and who might be about to break one of NOVA’s many unofficial rules.

My other roommate was a fellow teacher named Heather. The arrangement wasn’t terrible. It just wasn’t private.

Most afternoons I’d finish teaching, wander through the Shotengai interested me more and more with each passing day. I was also hoping to meet someone.

Not because I had arrived in Japan determined to find a wife. I had come looking for adventure, work, and maybe a little direction. If romance happened somewhere along the way, that would simply be a bonus.

Then one afternoon, sometime around late May, the classroom door opened and in walked Sachie Asahi.

The first thing I noticed was her haircut. It was incredibly short—shorter than mine—and on almost anyone else it probably wouldn’t have worked. On her it looked perfect.

The second thing I noticed was her T-shirt. Across the front was Andy Warhol’s Campbell’s Soup Can. Now at twenty-two I saw connections everywhere.

My first thought wasn’t, She’s wearing Warhol.

It was, She might actually know the Velvet Underground.

As soon as class ended, curiosity got the better of me.

“Miss Asahi,” I said, “can I ask you something?”

“Sure.”

“Do you know the Velvet Underground?”

She smiled.

“Yes I do. They are one of my favorite bands.”

Mine too.

That certainly got my attention. Looking back, that conversation probably lasted less than a minute. In memory it lasts forever.

Our First Two Dates:

A few days later I found myself lingering outside NOVA around lunchtime, pretending I wasn’t waiting for anyone in particular. I was waiting for her.

The door opened. Out walked Sachie.

“Are you heading home?” I asked.

“Yes.”

“Would you like to get some lunch?”

She thought about it briefly and said “I know a nice coffee shop.”

We walked over together. The owner was an older gentleman who made coffee the traditional Japanese way, pouring hot water slowly through paper filters with the concentration of a surgeon. We ordered sandwiches, lit cigarettes, and settled into conversation as though we’d been doing it for years.

At one point I looked at her cigarette and smiled.

“You know,” I said, “nurses probably shouldn’t smoke.”

Without missing a beat she smiled back.

“Teachers probably shouldn’t either.”

Touché.

It was such a small exchange. I’ve remembered it for twenty-nine years.

I wish I could tell you I played it cool after that first lunch. I did not.

Whenever our schedules lined up, I would find myself outside NOVA around lunchtime. Sometimes I really was heading out for lunch. Sometimes I was just hoping the door would open and Sachie would walk through it.

Sometimes it did.

As we were finishing our first lunch together I asked if I could call her. She said yes.

I called her the next morning around eleven, thinking this was an appropriate time. When she answered she laughed.

“Why didn’t you call earlier?”

“I didn’t want to seem too eager.”

“Eager would have been good.”

This was encouraging.

Our first proper date was a screening of Hal Hartley’s Amateur. I remember the movie mostly because I remember the evening. Hartley has always struck me as one of those directors I admire more than I love. I’m glad I’ve seen his films, but they never quite found a permanent place in my heart.

Near the end of the film she leaned toward me. Not to kiss me. Not yet.

She brought her lips close enough that I could feel her breath against my ear and whispered, in English,

“What is this music?”

I didn’t know but it didn’t matter. What mattered was that one moment of intimacy.

She was close enough that my entire body lit up. We didn’t kiss in the theatre. I think we held hands on the walk back to the car, but that’s about all. It was wonderfully innocent in the way that only the beginning of a relationship can be.

Kumamoto is not a very big city, and we quickly settled into a rhythm. We’d grab coffee, wander through the nearby Shotengai, or simply drive around with nowhere in particular to go. Looking back, it strikes me that we spent an awful lot of time in her little Mitsubishi. We couldn’t exactly go to my apartment—I lived with my boss, after all—and bringing a young American teacher home to meet your very traditional Japanese father wasn’t something either of us was ready for after a week or two.

So the car became our living room.

We’d park by the river or find a quiet place to talk, windows cracked just enough for the cigarette smoke to drift outside. We would make out in her parked car. I would finger her and she would return the favor. It never felt dramatic. It just felt…comfortable. We were both twenty-two, trying to figure each other out one car ride at a time.

I Join Washington Language School:

Around the same time another opportunity came along.

Washington English School offered better hours, more independence, and what sounded like a healthier working environment than NOVA. I handed in my month’s notice and, sometime around the middle of July, packed my two duffel bags yet again.

Leaving NOVA turned out to be one of the easiest decisions I’ve ever made. Fortunately, Washington was only a short distance away. The boss gave me the use of a cheap apartment, which was a bonus. For the first time since arriving in Japan I had a place of my own.

It wasn’t much. A small furnished apartment on the second floor of a walk-up, two tatami rooms, sliding doors, a tiny kitchen, an even tinier bathroom, a loft that was far too hot to sleep in during the summer, and just enough room for one young teacher who didn’t own very much.

I unpacked my books, stacked my CDs beside a little stereo, purchased groceries I barely knew how to cook, and slowly began settling into something that resembled ordinary life.

When I wasn’t teaching, I was usually doing one of two things. I was either with Sachie or working on a baseball simulation game.

That probably sounds stranger now than it did then. My uncle Steve had inspired me to try designing a tabletop baseball game based on real statistics, and I became completely absorbed by it. Most evenings found me surrounded by notebooks, pencils and baseball encyclopedias, trying to solve statistical puzzles. For weeks one pitcher, Lefty Grove, refused to cooperate. His adjusted ERA simply would not behave the way I wanted it to.

By August we were seeing each other almost every day.

One evening another young woman came on to me at a bar. I was briefly tempted. She was perfectly nice, and yet while talking with her I realized, almost in the middle of the conversation, that I didn’t want to be talking to anyone else except for Sachie.

The next day I told Sachie what had happened. She listened quietly and then she smiled. I said I would like to become exclusive. She agreed. Sometimes the most important decisions in life announce themselves quietly. This was one of those cases.

A few weeks later we decided to spend a weekend together in Tokyo.

Like so many romantic plans made by young people, ours was perfect in theory. Reality had other plans.

Our weekend in Tokyo was supposed to be the moment. We agreed we would have sex in our hotel room. By then we had been dating for a couple of months. We were crazy about each other, and it was time for the real intimacy to begin.

For dinner we had fish and soup and a few glasses of wine. Sachie was never much of a drinker, especially in those days. A few glasses of wine were enough to leave her happily, gloriously intoxicated. By the time we got back to the room she was laughing, stumbling a little, and having a wonderful time.

Then she collapsed across the bed. She was too drunk. Sex was off the table. We went to sleep

Somehow that failed evening made me like her even more. Real relationships, I was beginning to discover, aren’t built on perfect moments. They’re built on imperfect ones that two people survive together.

A week or two later back in Kumamoto life intervened in a somewhat dramatic way.

During the afternoon of August 31, 1997, I was walking home from work when someone stopped me on the street.

“Princess Diana died in a car accident.”

For a second I thought I’d misheard. I was shocked.

News traveled differently then. There were no smartphones and no social media. One stranger told another stranger, and for a few moments the whole world seemed strangely quiet. Such was the case here.

I walked the rest of the way home thinking about Diana, about Paris, about how somebody so famous could simply disappear in the middle of an ordinary night.

History has a curious habit of attaching itself to our private memories. I can’t think about Princess Diana without thinking about that afternoon.

Sachie came over later that afternoon. The mood was quieter than usual. We talked for a while, made coffee, listened to music, and eventually stopped talking altogether.

This time there was no hotel. No elaborate plans. No expectations. Just the two of us in my tiny apartment.

It happened naturally. We fell into bed together. We became lovers.

The sex was good; however I had nothing to compare it to. I was a virgin at 23. She had had some limited experience. I wore a condom for perhaps the first and last time. After that we weren’t trying to make a baby necessarily. If it happened it happened.

Outside, late-summer Kumamoto carried on exactly as it always had. Cars passed. Somebody’s television drifted through an open window. Somewhere in the distance a train moved through the evening.

The world hadn’t changed.

Mine had.

Looking back now, it’s tempting to search those first months for signs of what was coming.

Were there clues? Warnings? Promises?

Possibly.

There was simply a young American teacher who had wandered halfway around the world with two duffel bags, too many cigarettes, a head full of music, and absolutely no expectation of meeting the person he would build his adult life with.

And there was a young Japanese English student who happened to walk into one of his English classes wearing an Andy Warhol T-shirt.

The rest, as they say, is history.

Conclusion:

Sachie and I stayed together for twenty-nine years. We were married for twenty-seven of these.

Our marriage eventually came to an end just this spring, as many marriages do. Time changes people. Interests diverge. Careers pull in different directions. Habits change. Sex stops. Sometimes two people simply grow into different versions of themselves.

We tried our best. In the end our best was not good enough but we had fun along the way,

This essay belongs to two young people on the cusp of life. It belongs to coffee and cigarettes. To our long walks on the Shotengai. To Kumamoto. To our friends who were also young and looking to make a little life of their own.

To a little Mitsubishi with the windows cracked on warm evenings and making out passionately in the front seat.

To the Velvet Underground and an old man carefully pouring coffee.

To a whispered question in a dark movie theatre.

And to a grandfather who slipped an envelope into his grandson’s hand and said, “Go with God.”

Dedication:

For my wife, Sachie. And for my grandfather Bill Kolb, my hero. I love you Grandpa.

For Litzy Litz With an I My Babush Baby: A Love Poem 

“Isn’t she / pretty in pink.”
— Richard Butler

Baby, I love you so very much.
And darling, baby, I don’t mean just. 
I mean to ten thousand stars and back again,
And I’ll write this poem like a half-good man.

I’ve done this before and I’ll do it again,
But meeting you, baby, is the biggest win.
The greatest win of my whole strange life.
And someday soon you will be my wife.

Pause. Deep breath, dude. Don’t get all rude.
Spill the beans and spill the tea.
Don’t get all weak in the knees please. 
Baby Litzy, I love you clear to the moon,
And every time I see you, darling, I swoon.

I’ll fall to my knees and beg you please,
Say yes forever and stay with me.
For life, my darling. For all our days.
Forever and ever in every single way. 

And baby I’ll never, ever give you up,
For I am no chump, and I’ve taken my lumps. 

So Litzy, my Babush baby, pause.
Cause baby, just because because.
I’ve written poems since I was eight,
And some were good and some weren’t great.

And that’s the way these things can go.
Sometimes they shine, sometimes they blow.
I wrote for girls who said they were pearls,
Sweet little queens in shiny worlds.

But none were half as sweet as you.
And baby, yes, that much is true.
No candy shop or sugared peach
Could ever come within your reach.

Babush! Lol and OMG.
Baby, darling, can’t you see?
I love you like the bees love honey.
Like Wall Street loves money.

I love you like ships love the sea.
Like tall green forests love the trees.
And baby this may sound absurd,
But I mean every word.

I love you more than words can say,
More than the sunlight loves the day.
More than my father—and yes it’s true.
But more than anything: I love you.

Sweet baby babes, it’s been three weeks.
And still I cannot quit your cheeks.
Your apple cheeks are so soft and sweet.
They totally cannot be beat.

And if you’re sad or feeling blue,
I’ll always make some room for you.
Just rest your little head on me,
And baby all will gravy be.

Cause you’re four-eleven, cute and small,
And I’m six-three and standing tall.
Baby mine, I’m built like trees.
You rise up barely to my knees.

So I shall buy you some small place,
A little home with warmth and grace.
Or maybe some downtown apartment
Where all of our love can rest apace. 

And yes beneath the sheets we’ll creep—
OMG, baby, did I just say sheets?
But sheets, my darling, cannot lose.
They totally and fully rule.

I must have took some love-drunk pill,
And baby I am floating still.
Or maybe swallowed the whole jar.
I know that sounds a little bizarre.

But that’s just how I feel for you,

My Babush baby tried and true.
Don’t yawn, my pet, don’t drift away.
I need your sweetness every day.

I’m crazy for you. Wild it’s true.
And usually I’m mellow, 
But not around you. No no no.
Around you all my feelings do grow.

They rise and swell like ocean tides,
Like moonlit waves at eventide.
They crash and roar upon the shore
And then come rolling back for more.

The angels watch from high above.
The gods too, baby. That is love.
They watch you, me, and all mankind—
The short, the tall, the sweet, and the kind.

And sweetheart yes, you are my heart.
At least the biggest, finest part.
Though room remains there for my son.
And baby I have only one.

He means the whole wide world to me.
Just like you do, my honey bee.

Baby baby, my Litzy Litz honey.

I have some money. And you do too.
But our love runs deeper than money, honey,
And baby I know that much is true.

And maybe that sounds a little funny.
Laugh out loud. Let’s laugh awhile.
Cause baby we are the cool-kid crowd,
And darling we do it all with style.

And I shall buy you a shining ring.
Yes dear, the ring is the thing.
No wait—make that two instead.
One for your hand and one for my head.

Platinum maybe, or jeweled with light,
Like the crown you wear day and night.
Princess mine, yes the ring’s the best.
And baby your beauty outshines the rest.

And I shall worship down at your feet.
And honestly baby, ain’t that neat?
Then I shall stand and carry you slow
Back to our room where the soft lights glow.

And I just said bed—yes that’s true.
That is just what I said to you.
With giant pillows that puff and billow,
Soft as clouds or a little marshmallow.

Or maybe baby it’s a waterbed.
Wouldn’t that rule? Enough said.
We’ll sleep together like little mice,
Warm and tiny and cozy and nice.

And ain’t they cute? Well shoot, they are.
Baby you shine like a lucky star.
Our first date now is drawing near.
OMG baby, it’s almost here.

And we have spent long hours on phones,
So neither of us feels all alone.
Cause baby you always carry me,
As I carry you through stormy seas.

And I don’t know much, but this I know:
My love for you will just grow and grow. 
I’m fifty-two and you are fifty,
And honestly baby, ain’t that nifty?

I don’t want younger girls no more,
Even the pearl-like beauties ashore.
Cause baby I only and fully want you.
Forever and ever. Tried and true.

Bank it sweetheart. Trust what I say.
Everything’s gonna be fine someday.
Pause dude. Baby just chill.
Don’t go and spill your ink at will.

Don’t splash your words all over the page.
That is the path to readerly rage.
Keep it moving. Keep it light.
Keep the rhythm warm and bright.

Cause baby this poem must soon end,
But I shall always your heartstrings mend.
If sadness finds you, I’ll stay nearby.
I’ll hold your hand and I’ll never lie.

For I will never break with you.
My heart stays faithful, tried and true.
As faithful as wind over oceans blue,
And sweet as melons in morning dew.

And I shall take you to heaven and back,

With love and warmth and midnight snacks.
And heaven, darling, must surely be
Somewhere with you right next to me.

So come here close now, baby mine.
Your little hand fits well in mine.
And I shall kiss your mouth so sweet,
And places farther down beneath—

OMG baby, I just said south.
Quick, back again now to your mouth.
Your lips, your nose, your hips, your eyes,
The stars reflected in midnight skies.

And all of you shall belong with me,
As mine belongs completely to thee.
For sure, sweetheart. Forever true.
Litzy Litz baby—I love you.

Dedication:

For my darling Litz. I am so happy that you are in my life baby. I promise to love you forever and a day. I love you.

The Great Roast of Bill Simmons, The Podcasting GOAT

Note: Bill Simmons has many gifts, but none more enduring than his ability to take a perfectly good idea and turn it into a totalizing worldview. Chief among these is his obsession with “who gets the keys,” a concept that began as a useful shorthand for late-game NBA hierarchy and has since metastasized into a governing principle for all human activity. In Simmons’ hands, the question is no longer who closes Game 7, but who closes anything: marriages, movies, bands, revolutions, and possibly even the Enlightenment. It is a framework so elastic that it explains everything and therefore, in a quiet and almost admirable way, explains nothing. Yet Simmons returns to it again and again, like a man who has discovered fire and insists on using it to cook every meal. The result is less analysis than ritual: a familiar incantation that reassures both host and listener that control exists, that someone always has it, and that identifying that person is the highest form of understanding. Whether this is insight or compulsion is an open question, but in the meantime, Simmons has the keys—and he’s not giving them back.

I. The Obsessive With the Keys

Bill Simmons is a strange and singular figure in American media, a man whose greatest innovation may have been to take the interior monologue of a slightly obsessive sports fan and publish it wholesale, unfiltered, and then slowly convince an entire industry that this was not only acceptable but essential. He is not quite a journalist, not quite a commentator, and not quite a comedian, but rather a hybrid form: a “Sportish Guy,” as Cousin Sal once put it, who treats every game, every movie, and every stray anecdote as part of a single, ongoing argument about how the world works. Central to that argument is his enduring fixation on control, on agency, on the question he returns to again and again with the devotion of a man checking the locks before bed: who gets the keys?

It is tempting to dismiss this as a bit, and in some sense it is, but like all of Simmons’ best bits, it has metastasized into something larger and more revealing. What began as a useful shorthand for late-game NBA hierarchy—who has the ball, who takes the shot—has expanded into a general theory of human behavior. Quarterbacks have the keys. Movie characters have the keys. Entire bands, dynasties, and historical figures are evaluated based on whether they had, lost, or never quite secured the keys. That Mark Sanchez could, for a brief and inexplicable moment, be discussed in these terms tells you less about Sanchez than it does about Simmons’ commitment to the framework. He does not particularly care if the fit is perfect. The system must be applied.

This is what makes Simmons both compelling and faintly ridiculous. He is, at heart, a “who’s on my team” guy, a loyalist who rewards proximity, familiarity, and shared history, sometimes to a fault. Former colleagues have occasionally noted that he can cool on people once they leave his orbit, a tendency that reads less as malice than as a kind of emotional sorting mechanism: you are either in the ecosystem or you are not. Some, like Kevin O’Connor, speak warmly of early generosity—gifted shirts, guidance, a foothold in Los Angeles when money was tight. Others have been less charitable, and the occasional critique, including a much-circulated piece in The New York Times, has tried to frame Simmons’ blind spots, particularly around race, as more systemic. These critiques are not wholly without merit, but they often feel slightly overdetermined, flattening a personality that is better understood as idiosyncratic rather than ideological. Simmons himself tends to respond not with grand rebuttals but with motion—hiring voices like Van Lathan, insisting, plausibly, that such moves were already in progress, and continuing on as if the conversation will resolve itself over time.

There is also, undeniably, an ego in play. Simmons has built an empire—Grantland, then The Ringer—largely on the strength of his own voice, and he is not shy about asserting it. Stories persist, as they do in any media ecosystem, including the long-running rumor that he played a role in Magic Johnson’s exit from NBA Countdown, a claim Simmons has repeatedly and emphatically denied. More verifiable is the moment that effectively ended his ESPN tenure: a live broadcast of NBA Countdown in which, after a colleague spoke at length, Simmons leaned in with heavy, unmistakable sarcasm—“Oh, is it my turn to talk now?”—a line that was funny, revealing, and, in the context of corporate television, fatal. It was the voice of the columnist breaking through the format, the irrepressible instinct to comment on the comment, to seize the keys even when the structure said otherwise.

What makes Simmons unique, and worth writing about at all, is that these contradictions—generous and insular, insightful and reductive, earnest and performative—are not bugs but features. He is a weird obsessive who has turned his obsessions into a career, and in doing so has given us a language that is at once clarifying and absurd. He loves the game, he loves the conversation around the game, and above all he loves the feeling that somewhere, in any given moment, someone has the keys.

II: The Bits That Ate the Brain

If the keys are the theory, the bits are the practice. Simmons has always understood that repetition is power: say something often enough, with just enough conviction, and it graduates from joke to canon. Thus “greatest stickman,” a phrase that should have died in a driveway, becomes a legitimate category, and suddenly Burgess Meredith is being floated as an all-timer. “Sal, Sal, BM was the greatest stickman of all time. Every lady wanted a ride.” It is ridiculous, obviously, but also irresistible. The specificity disarms you. The confidence sells it. The framework expands.

This is the Simmons trick: take a private-language riff and run it until it becomes a public one. It does not matter that no one else has ever considered ranking “stickmen.” What matters is that Simmons has, and that he will return to it, again and again, until you find yourself half-convinced that you, too, should have an opinion. It is analysis as inside joke, inside joke as analysis.

III. The Ecosystem

No system survives without a supporting cast, and Simmons has assembled one of the most durable in podcasting.

There is Cousin Sal, the indispensable counterweight, quicker and often funnier, whose primary function is to puncture Simmons at exactly the right moment. The Vegas trips are their shared masterpiece: two grown men insisting, year after year, that this time they will behave differently, and then not. Simmons, improbably, claims that he only smokes in Vegas. No one believes this. The morning-after pod is the payoff—hungover, frayed, the truth leaking out in fragments. “I only had three cigarettes last night,” Simmons offers. Sal, without missing a beat goes: “Yeah, more like three lighters.” It is the kind of line that ends the discussion because it cannot be improved.

There is Joe House, lawyer by day, chaos agent by night, who turns every appearance into a small act of self-destruction. “House Eats” remains a high-water mark: an adult man consuming Chinese food until he vomits, captured and distributed as legitimate sports media content. It should not work. It works perfectly. Drunk House—slurring, swearing, denouncing Daniel Snyder with operatic intensity—is not a bug but a feature. Simmons does not rein him in; he amplifies him. The ecosystem thrives on this permissiveness.

And then there is Nephew Kyle, the quietly essential, publicly baffling producer whose qualifications are, at best, opaque. The nepotism is acknowledged, even embraced. Simmons does not pretend otherwise. He does not have to. The show goes on. The levels are sometimes off. The energy is always on.

IV. The Interviews: High Risk, High Variance

Simmons as interviewer is a study in range. At his best, he is disarming, patient, and genuinely curious, capable of extracting moments that feel both candid and consequential. His conversation with Al Michaels is a case in point: Michaels, relaxed, recounts the day of the O.J. chase, including the now-legendary call-in where a supposed eyewitness punctuates his tip with “Baba Booey.” The co-host takes it seriously. Michaels does not. “It’s a joke, dude,” he essentially says, and in that moment you see the difference between professionals. Simmons knows enough to step back and let the story land. It is radio as it should be: a master talking, a host listening.

The interview with John Skipper is another apex moment. Post-ESPN, Skipper speaks with a level of openness that borders on the shocking—cocaine use, morning routines, the normalization of behavior that would end most careers. Simmons guides rather than pushes, and the result is a “huge get,” the kind of conversation that justifies the entire enterprise.

At the other end of the spectrum sits the Denzel Washington interview, a minor classic of mismatch. Washington arrives as if for one kind of conversation; Simmons is clearly expecting another. The opening is awkward, the rhythms off. To his credit, Simmons does not retreat. He leans in, tries to find common ground, and eventually does, or at least something like it. It is not a triumph, but it is revealing: the limits of the format, the limits of the host, the persistence of the effort.

V. Homerism as Method

Simmons’ greatest cultural contribution may be the legitimization of homerism. Before him, fandom was something to be managed, disclosed, occasionally apologized for. With him, it becomes the point. He is, unapologetically, a Boston guy: the Boston Celtics are not just a team but a lineage, a narrative, a near-mythological entity anchored by figures like Larry Bird, whose legend grows incrementally with each retelling. The takes are, at times, outta control. They are also, in their way, coherent. Simmons is not pretending to objectivity. He is offering a perspective, and trusting that the audience will meet him there.

This approach extends beyond basketball. Baseball, once a central obsession—AL keeper leagues, granular analysis—fades over time, dismissed as too long, too slow, no longer aligned with the rhythms of his life or his listeners’. Basketball remains the core competency, the area where his knowledge is both deep and defensible. Everything else orbits around it.

VI. Family and Formation

The personal mythology is never far from the surface. Simmons’ father, a longtime Celtics season-ticket holder, is both character and audience, the origin point of the fandom that would become a career. The pride is evident, even when unspoken. The access—courtside seats in the 1970s—becomes part of the narrative, a credential as meaningful as any byline.

His mother, less present on the pod but frequently referenced, provides another axis: a love of movies, a different kind of cultural literacy that feeds into Simmons’ broader interests. The recurring mention of being a child of divorce functions as a kind of grounding note, a reminder that the voice, however confident, has origins in something more fragile. He seems, by most measures, to have come out fine.

VII. Drift and Discipline

As the empire grows—Grantland, then The Ringer, now under the umbrella of Spotify—Simmons changes in ways both subtle and obvious. He fades certain voices who no longer fit the evolving brand: Adam Carolla, once a regular presence, becomes less so; Michael Rapaport, similarly, drifts out of the rotation. The official reasons are varied—tone, fit, the simple passage of time—but the underlying dynamic is familiar. Simmons is, at heart, a “who’s on my team” operator. The team changes. The roster turns over.

And yet, it is hard to shake the sense that the affection remains. These are not clean breaks so much as quiet reassignments, the byproduct of a system that requires a certain level of control. Spotify money, corporate expectations, the need to maintain a particular tone—these exert their own pressure. The outta-control energy that defined earlier iterations of the pod is still there, but it is managed, channeled, occasionally held back.

VIII. The Countdown Moment

If there is a single scene that captures Simmons in miniature, it is the one that ends his ESPN tenure. On NBA Countdown, a colleague speaks at length. Simmons waits. And waits. And then, with a level of sarcasm that is both unmistakable and, in context, disastrous, he interjects: “Oh, is it my turn to talk now?” It is funny. It is honest. It is, within the rigid structure of live television, unacceptable.

He is removed not long after.

The moment endures because it reveals the core tension: Simmons the columnist versus Simmons the employee, the impulse to comment versus the requirement to conform. He cannot quite suppress the former, even when the latter demands it. He reaches for the keys, even when they are not his to take.


VIII. Conclusion

Bill Simmons is the GOAT podcaster, full stop, and it’s worth saying that clearly at the outset because we only roast the ones we love. Bill Simmons has given us an entire language—keys, stickman, Vegas nights, Sal lines, Drunk House—and if you’ve been along for the ride, those bits don’t wear out, they compound. They get funnier with time, richer with context, a kind of private shorthand that becomes, almost accidentally, a shared culture. You either hear “three lighters” and laugh immediately or you don’t, and if you don’t, there’s not much point explaining it.

This is part of what makes Simmons both beloved and, in certain circles, a little contentious. He has clearly made enemies—inside ESPN, across the broader media landscape, and occasionally among former employees—and while it’s easy to chalk this up to ego or looseness, the better read is that the looseness is largely performative. Underneath the hangout vibe, the teasing, the Nephew Kyle chaos and the Drunk House indulgence, there is a very real set of standards, and Simmons enforces them. He is, at heart, a “who’s on my team” operator, and the team matters. People drift out. Some of that isn’t pretty. Most of it, however, is consistent with how he’s always operated: loyal, selective, and ultimately in control of the room.

At the same time, there is a sense now that Simmons is, if not slowing down, then at least rounding off the sharper edges. He talks openly about retirement in a way he didn’t a decade ago, and you get the feeling that he is aware, at some level, of the limits of the bit. Will he be seventy-five, still ranking stickmen and assigning keys? It’s hard to see it. He’s a boss now, a central figure inside Spotify, with responsibilities that extend well beyond the pod. The insurgent has become the institution, and while the voice is still there, it’s necessarily more managed than it once was.

There’s also the simple fact that Simmons is no longer a writer in the way he once was, and he knows it. The old columns—the mailbags, the trade value pieces, the obsessive digressions—have given way to the pod, to conversation, to rhythm. He jokes that his fingers don’t work anymore, and like most of his best lines, it’s funny because it’s partly true. The Book of Basketball stands as the monument to that earlier phase: long, ambitious, slightly out of control in the best way, complete with the famous pyramid (Jordan at the top, Magic above Bird, a decision that still tells you everything you need to know about him). But the shift from writing to talking isn’t a decline so much as an evolution. Simmons was always more voice than text anyway. The medium finally caught up to the man.

If and when he does step back, what we lose is not just a podcast or a brand but something rarer: a genuinely original voice that bent an entire corner of the media world toward itself. Plenty of people analyze sports. Plenty of people talk about culture. Almost no one has managed to fuse the two into a single, durable, endlessly riffable system the way Simmons has. The keys, for all their absurdity, are real in that sense. He found them early, used them often, and built something that will outlast the bit itself.

And if he eventually decides to set them down, or even just hold them a little more loosely, it will mark the end of a run that, for all its contradictions, was unmistakably his.

The Adventures of the Thin Man and Andrea II CHAPTER 4: The Thin Man’s Great Grandfather in Moscow I

CHAPTER IV — THE ANNEX

Scene One: The Office / The Invitation

The office was already in its late morning rhythm, which meant it had stopped pretending to be anything other than itself. Papers moved in shallow stacks. Ink dried on fingers that did not belong to the men using them. Conversations rose and fell without consequence, like breath in a cold room.

Niko sat at his desk with the quiet concentration of someone trying to stay slightly ahead of his own life. The work was not difficult. It was worse than that—it was repetitive in a way that made thought drift toward other, less supervised subjects.

The Southerner arrived without announcement, as he always did. He never seemed to enter a room so much as appear already inside it, as though the office had quietly agreed to produce him when needed.

He leaned on the edge of Niko’s desk.

“You are still here,” the Southerner said.

“I am paid to be,” Niko replied.

“That is not the same thing,” the Southerner said, smiling faintly. “Come along tonight. There is a place. A bathhouse annex. Dice. People worth meeting. You will find it useful.”

Niko looked up. “Is this work?”

“It is better than work,” the Southerner said. “It is instruction.”

Across the room, the Teutonic Knight cleared his throat with deliberate severity. He approached, holding a single sheet of paper as though it were evidence in a moral trial.

“This document,” the Knight said, “has migrated again.”

Niko glanced at it. “It appears to be in the correct file.”

“It was not there yesterday,” the Knight insisted.

“It is there today,” Niko said.

The Knight stared at him as though the universe had briefly failed to obey.

The Southerner sighed softly. “He is correct, you know. The paper is now where it should be.”

The Knight hesitated, recalibrated his indignation, and finally withdrew with a small, wounded dignity.

When he was gone, the Southerner tapped Niko’s desk twice.

“Seven,” he said. “Be there at seven.”

And then he left, as if the conversation had already been archived.


Scene Two: The Bathhouse Annex / Anya Appears

The bathhouse was warmer than the street in a way that felt almost indecent. Steam softened the edges of everything—voices, money, judgment, time. The annex behind it was not officially part of anything, which made it more important than anything that was.

Dice moved across low tables. Drinks appeared and disappeared, something without accounting. Men spoke in half-sentences that assumed agreement. Somewhere, someone laughed too long at a joke that had already ended. The crowd was a mixture of civil servants, military men, commercial travelers, and the odd semi-criminal element that such places always attract.

The Southerner greeted people as he passed, each nod suggesting a prior history Niko had not yet been invited into.

“Here,” the Southerner said at last, guiding him toward a table where the air felt slightly denser. “Watch first. Then play.”

Niko did not ask questions. He rarely did.

He sat.

The dice were small and worn, softened by use. They looked less like objects than habits. The first roll came quickly. Loss. The second, neutral. The third, unexpectedly favorable.

He felt something loosen in him—not relief exactly, but attention.

That was when she appeared.

Not entering so much as arriving within his field of perception, as though she had been standing just outside his awareness and decided to step in.

Anya did not look at the dice at first. She looked at him. Then she smiled slightly, as if confirming something she had already guessed.

“Buy me a drink,” she said.

It was not a request that demanded urgency. It was a test that did not require refusal. Niko paused just long enough to register the tone, the cost, the structure of the moment.

Then he nodded. “Of course.”

She accepted this as expected behavior.

Later, much later, after the dice had lost their clarity and the room had begun to fold into itself, Niko walked back through the city alone.

His lodging was a narrow stairwell building where the air smelled faintly of coal dust and old wood. He climbed slowly, as if each step were part of a decision he had already made.

In his room, he did not undress properly. He sat on the edge of the bed with his shoes still on, then removed them with deliberate care. Anya remained in the corner of his thoughts, not as a person exactly, but as a continuity.

He imagined a version of the future where she was simply present in it without explanation. Where evenings were not entered alone. Where dice were occasional rather than defining. Where risk could be contained rather than pursued.

He turned onto his back. The ceiling was damp in one corner. He would have to get that looked at, that is if his landlord could ever be located.

He fell asleep thinking, not of winning, but of Anya.


Scene Three: Two Weeks Later / The Restaurant

The restaurant was modest in the way things become modest after expense has been calculated too carefully. The light was steady, neither flattering nor cruel. Anya arrived slightly late, which made her presence feel more intentional when she finally appeared.

Niko stood when she entered, then immediately felt slightly foolish for doing so.

“You didn’t have to wait,” she said.

“I did not wait,” he replied. “I arrived earlier.”

This was technically true and socially irrelevant. They ordered simply. Niko paid without hesitation, though the number at the bottom of the bill lingered in his mind afterward like a minor echo.

Anya watched him over the rim of her glass.

“You are not very careful with money,” she said.

“I am careful in other ways,” he said.

“That is what men always say,” she replied, not unkindly.

There was a pause between them that was not awkward, but not empty either. It held its own structure.

When they left, she took his arm briefly—not as possession, but as orientation. He did not misread it. It was one night.

That would matter later.


Scene Four: The Morning / Anya’s Apartment

Morning arrived without ceremony.

Niko woke to the sound of movement in another room, not hurried, not performative. The ceiling above him was plain. The air smelled faintly of tea and something warm that had been cooked without ambition.

He lay still for a moment, listening to the normality of it. Anya entered carrying a cup of tea. She set it on the table beside the bed without comment.

“You stayed,” she said.

“I did,” Niko replied.

“That is not always how it goes,” she said.

“No,” he said.

She sat at the edge of the bed briefly, as if confirming that the space between them still existed in a usable form. Outside, the city was already functioning. Inside, nothing required immediate adjustment.

Niko took the tea. It was slightly too hot. He did not complain.

Anya watched him drink it, then stood.

“You should go soon,” she said, not unkindly.

“I know,” he said.

He did not move immediately.

And for a short while longer, neither of them tried to name what had already begun to form between them.

The Adventures of the Thin Man and Andrea II: The Thin Man’s Son. CHAPTER 3: The Thin Man in Costa Rica

Matt texts the Thin Man before he has even fully decided to.

There is a kind of threshold in sending a message like that, where intention arrives slightly after action. The screen shows the name and then the words appear as if they were always going to exist.

Found her.

There is no immediate reply.

Matt goes to the hotel rooftop pool instead, because the body refuses to remain still when the mind is doing work it cannot complete. The city below is a port city, functional rather than beautiful, ships moving like punctuation marks across water that does not care about narrative.

He swims slowly. Not exercise. Just repetition. Something to keep him inside himself.

The Thin Man arrives without announcement.

Matt sees him later in the lobby, as if he has always been there and only now decided to become visible. There is nothing theatrical about his movement. He is dressed simply, unremarkable in a way that only becomes noticeable after you have already started paying attention.

They do not greet each other like friends. They never have. They greet each other like continuity.

Matt watches him cross the space and feels, not for the first time, that proximity to him changes the temperature of events.

LUCÍANA

The café is near the port, where the air carries salt and fuel in equal measure. Luciana arrives slightly early, not because she is nervous, but because she is efficient. She chooses a table where she can see the entrance without appearing to be watching it.

When Niko arrives, she recognizes him immediately, though recognition does not translate into welcome. Time has done what time does, which is soften edges without removing structure. He is older now, but not unfamiliar in the way she expects him to be unfamiliar.

They sit.

For a long moment, neither of them performs memory. When they finally speak, it is careful, almost formal. He asks about her life. She answers without inviting him into it. There is warmth in her tone, but it is bounded. Controlled.

She tells him about their son. He listens without interrupting.

“He is in Dubai,” she says after a time. “He is working in media. Content. Travel. He is doing well for himself.”

Niko nods once. No visible reaction beyond that. But something in the air shifts slightly, as if a long thread has been acknowledged without being pulled.

Luciana continues. She has a daughter now. A marriage. A life that has moved forward without apology. When Niko asks nothing more, and she is briefly grateful. Then she tells him, clearly and without cruelty, that this is not something she wants reopened.

He understands. He does not argue. He never argues with time.

MATT THOMAS AT THE HOTEL

I am still at the hotel when he returns. He does not look like a man who has just been refused something. He looks like a man who has confirmed a hypothesis and chosen not to act on it. There is a difference, and I am beginning to understand it.

I ask him if he saw her. He says yes.

I ask what she said. He does not answer immediately. Then he tells me about Dubai, about the son, about the fact that life has continued in a direction that does not require his permission.

I wait for more. There is no more.

That is when I realize how little I actually know about him, even now. Later that night, I finally ask the question I have been circling since Tokyo.

“What is your real name?”

He does not look surprised.

He never looks surprised.

He says he is from Georgia. That his name is Niko. That he was born in 1977.

Nothing more.

And somehow that is enough to change the entire shape of what I thought I was holding.

CODA — MATT THOMAS IN KOYTO

I am back in Kyoto, but I am not fully back in anything that resembles ordinary life. The school still exists. I still teach. I still perform the version of myself that can explain narrative voice to students who are mostly thinking about lunch. I have had readings now—one in Kyoto, one in Tokyo—and people are starting to treat me as if I might become something recognizable.

It does not go to my head. But the Thin Man does. He’s always there.

We talk on Signal in fragments. Nothing structured. No schedule. Just interruptions in time that feel more real than the rest of the day. I sit in shisha places after work and try to write, but what I am actually doing is waiting for the next message.

Book II is already taking shape in my head.

I am just not sure yet whether I am writing it is writing me.

The Adventures of the Thin Man and Andrea II: The Thin Man’s Son. CHAPTER 2: Matt Thomas in Costa Rica

COSTA RICA — LATE FEBRUARY

Before I got on the place for Costa Rica the school was still trying to pretend this was still a normal conversation.

Vice Principal Nakata-san called me into the office with the kind of politeness that always signals something is already decided. The room was too bright, the air-conditioning too strong, the framed notices on the wall insisting on order. I sat down expecting administrative concern and got something closer to procedural disbelief.

“If you leave during term time,” Nakata-san said carefully, “your employment status may be affected.”

I nodded as if this was news I could process. Inside my mind was pure white. I said I understood. but I was going anyway.

There was a pause after which neither of us spoke.

“I am not firing you,” Nakata-san added, almost gently. “But you are… on thin ice.”

I thanked him, which felt like the wrong response but also felt like the only one available. When I left the office I was not thinking about consequences in the way institutions intend. I was thinking about distance, and how quickly it can become irreversible.

The flight to Costa Rica felt like a correction rather than a journey.

I watched the map on the screen and thought about how absurd it was all becoming. Somewhere over the Pacific, I opened my laptop and tried to write some notes, but nothing useful formed. Everything kept collapsing back into the same name.

Luciana Solís.

I did not yet know what I was looking for. I only knew that stopping now would mean admitting the shape of the obsession too clearly.

San José arrived humid and unceremonious. Costa Rica did not announce itself so much as absorb you. I moved through it with the slightly displaced awareness of someone who has read too many fragments of a story before seeing the whole thing.

I started where any amateur investigator starts: public record offices, municipal archives, online registries that are barely maintained but still technically alive. Marriage records, birth records, civic logs that feel like they were designed to discourage curiosity rather than enable it.

The work was slow and unglamorous. Most of it was administrative noise.

And then, on the third day, something aligned. A record. A name. Luciana Solís.

It is not dramatic when I found it. There was no cinematic recognition, no surge of certainty. Just a quiet moment where the page refused to behave like a coincidence.

I sat back from the screen and realized that my hands were slightly cold.

That is when I knew I was no longer guessing. This was the Thin Man’s son’s mother.

The Adventures of the Thin Man and Andrea II: The Thin Man’s Son. CHAPTER 1: The Thin Man in Tokyo

TOKYO — 1:13 PM, late January

He wakes up without remembering the descent. Not the drinking. Not the last message. Not the shape of the night leaving his body. Just the slow return of weight.

The house is rented, not lived in. A clean, architectural expanse in western Tokyo—glass, pale wood, too much air between objects. The kind of space that does not ask questions because it assumes nothing will answer.

He sits up once, then stops. 1:13 PM. The afternoon has already begun without him. He lies back for a moment and listens to the silence of money maintaining itself. There is a bottle on the floor beside the bed. Half-finished. Warm now. He doesn’t look at it again.

He stands, showers without thinking, dresses in the order that muscle memory dictates: black shirt, trousers, jacket. No tie. Never a tie unless someone insists.

His phone is already lit when he returns. Two messages. One from Tomoyo.

“Weekend still okay?”

One from Mina.

“Bar As One. Late.”

He reads them without responding yet. Then another notification appears. A different rhythm. Alejandro.

No name attached. Just the letter cluster, like something filed incorrectly in a system that never bothered to correct itself.

“Need you in Akasaka. KBS situation. Quiet, but messy.”

He stares at it longer than he should. Then:

“Corporate accounting discrepancy. Possibly internal extraction.”

That word—extraction—is always a translation problem. It never means only one thing. He exhales, once.

And for the first time that day, he is fully awake.

KYOTO — That Same Day

I am in my classroom when I see the notification. I’m not during anything important. Just one of those pauses between things where students are pretending to work and I am pretending not to notice they aren’t.

The phone is face down. I flip it. It’s Signal. I don’t even check the sender first anymore; I know it’s from the Thin Man.

“Akasaka. KBS. Quiet job.”

That’s it. No greeting. No explanation. No punctuation beyond necessity.

I look up at the room. The students are writing essays on narrative voice, ironically enough. I tell them to keep going and step into the hallway.

Outside, the corridor smells like floor wax and winter coats that never fully dry. I write back:

“You’re back?”

A pause.

Then:

“Always.”

I sit down on the stairs and realize I’ve been waiting for this message more than I admitted to myself. Not because I want the job. Because when he appears, the world becomes legible again.

Even if it shouldn’t.

TOKYO — 5:57 PM That Same Day

Akasaka in daylight is almost offensive in its normality. Glass buildings pretending they are neutral. People moving like they have somewhere else to be even when they don’t. He enters KBS through a side entrance.

Not invited. Not uninvited. Just expected. The problem is explained in fragments.

A mid-level finance manager has flagged irregular payments in a production budget. Someone else has flagged the flag. A third layer has erased the second.

Now everyone is quietly pretending nothing happened while insisting something must be done. He listens. He does not take notes. He asks three questions.

The answers contradict each other in useful ways.

By 4:02 PM, he knows what happened. By 4:07 PM, he knows who benefited. By 5:12 PM, he knows why no one will say it out loud.

He leaves without announcing that anything is resolved. This is the job. 

On the street outside, he finally replies to Tomoyo who he has beeb seeing for about two moths now:

“Saturday still okay.”

Then Mina:

“Later.”

Then Alejandro:

“Done.”

No embellishment. No summary. Just closure.

KYOTO — 10:02 PM That Same Day 

I am in a shisha place near Sanjo when he updates me. Not the kind of shisha place you imagine. Cleaner. Quieter. Students pretending to be older than they are. A place where time slows down but doesn’t stop.

I have a draft open on my laptop. A text arrives. It is about him. It is always about him these days.

“KBS resolved.”

That’s all. No story. No detail.

I type:

“What was it?”

Three dots appear. Disappear. Return.

“Accounting.”

That word again. He uses it the way other people use weather reports. I lean back.

Outside, Kyoto is doing its careful thing—bicycles, soft neon, the sense that nothing ever fully arrives here.

I realize I’ve stopped writing fiction and started writing evidence. 

TOKYO — 11:35 PM That Same Night

Bar As One is half-lit, as always. Mina is behind the counter like she has been there longer than the building. She does not ask what happened in Akasaka. She never asks anything that can be answered incorrectly.

He sits and orders a whisky ginger. They talk about nothing that matters. Tomoyo arrives later. She wears corporate black like it is a second job. She kisses him once, briefly, like a scheduled interruption. He notices everything about her that is real and nothing about her that is performance. That is what he likes about her.

At some point, his phone vibrates again. A new Signal message. It’s from Matt.

KYOTO — 11:26 PM. That Same Night.

I’m still at Shisha, still thinking about the Thin Man, I shouldn’t be doing this in public. But I am.

Me:

“I think I understand what you do in Tokyo.”

A reply comes faster than expected.

“You don’t.”

I almost smile. Then I don’t. I type:

“I’m going to Costa Rica.”

This time there is a long pause.  Then:

“Why.”

I look at the ceiling of the shisha place. Smoke moves like it has intention.

“Luciana.”

The name sits there on my screen like it has weight. I don’t know if he will respond. 

But I know I’ve crossed a line.

TOKYO — 12:14 AM The Next Morning

He reads the name once. Then again. Luciana.

Not spoken in years. Not held in any current system. Not part of any job file. He steps outside for a smoke. 

Akasaka is quieter at night, but not safer. Just less honest about itself. He does not ask Matt not to go. That would be meaningless.

Instead he writes:

“Don’t dig wrong.”

Then, after a pause:

“If you’re going, be precise.”

He puts the phone away. Tomoyo is still inside, laughing at something someone said that is not funny. Mina is polishing glasses that are already clean.

He thinks, briefly, of leaving Tokyo again. Not because something is wrong. Because something has started.

And that is usually enough.

KYOTO — 12:44 AM The Next Morning

I read his message twice.

Be precise.

As if precision is the problem. As if I have ever been anything else. 

I close my laptop. Outside, Kyoto continues as if nothing has happened. But I know it has.

I have a name now. And names are how you begin to lose your distance from things.