The Days and Nights of the 50s, 7/25/26. He Gets on Base.

Epigraphs:

So you wanna get out?
Let me draw a map

–Superchunk

Good sex it never makes you feel hollow
Good sex it never makes you clean

–Kevin Drew

I watched your face die backwards
Little baby in my memory
You told me victory’s sweet
Even deep in the cheap seats

–Conor Obrest

I. Morning

I slept better than I have in a long time. As best as I can recall, I went to bed around 12:40 AM. and woke up around 6:40 AM. Six hours is not necessarily a full night’s sleep, but lately it has felt like a luxury. I woke up clear-headed, made coffee in my room, and headed down to the Lawson around the corner for another one. I picked up some potato chips while I was there, wandered back to the hotel, and settled into the morning.

The first order of business was practical. I checked my messages, replied to my son Hugh, and told him I’d be happy to swing by home on Monday as long as he let me know what time he expected to be home. “Love, Papa,” as always. I checked in on Elliott as well. Nothing had changed. As of this writing, we’re still meeting at 6:30 this evening at a beer bar in southern Osaka, and I am looking forward to it.

Once these logistics were out of the way, my mind drifted, as it sometimes does, toward movies and television.

I started thinking about The Sopranos. I’ve watched this show all the way through twice, and I’ve revisited a number of episodes over the years. I think James Gandolfini and Michael Imperioli both give remarkable performances, and there are many individual scenes I genuinely love. Even so, I’ve gradually realised that David Chase’s aesthetic simply isn’t mine. Whether the repetition is intentional or not—and I suspect it is—I find both the storytelling and the character arcs to be cyclical.

The performances remain compelling, but the show continually circles back over the same emotional territory. I understand why so many people consider it one of the greatest television dramas ever made. I don’t. I like it and I’m glad I watched it, but I don’t imagine I’ll ever watch the series again.

Thinking about The Sopranos naturally led me to the dialogue that has stayed with me over the years. Not necessarily the greatest lines ever written, but the ones I find myself returning to.

Roger Wade, in The Long Goodbye, pours two glasses of anisette and says to Philip Marlowe, “Take that goddamn J. C. Penney tie off.”

Marlowe calmly replies, “I’m happy to drink with you, but I’m not taking my tie off.”

I don’t know why I love that exchange so much, but I always have.

Another favorite comes from Godfather II. Michael Corleone’s sister comes to him with her new boyfriend Merle to ask Michael for money.

“Connie, I don’t know this Merle. I don’t know what he does. I don’t know what he lives on. Tell him you’re never going to see him again, and come and live with me in Tahoe.” She does of course. It’s funny, oddly romantic, a little menacing, and super funny.

Then there’s The Wire. Bodie has always been my favourite character, and one of my favourite exchanges comes in Seasons 3 shortly after Cutty gets out of prison.

“I’m surprised Avon lets y’all get your heads up.”

Bodie shrugs.

“Sometimes you got to.”

Four words. An entire philosophy.

Seinfeld contributes one as well. Kramer proudly shows Jerry his silk boxer shorts and encourages him to buy a pair. Jerry politely declines.

“No thank you. They’re just a little too delectable for me.”

Perfect.

Finally, there’s Michael Clayton. Arthur Edens has come apart at the seams strips off in the deposition room. Michael flies to Wisconsin to rescue him, and after a brief argument simply says,

“Let’s get out of Milwaukee and we’ll talk about it.”

Sometimes a single sentence can contain an entire friendship.

As I thought about these great quotes, I realized something that hadn’t quite crystallized before. I don’t dislike slow films. I dislike static ones. I love Tarkovsky, but I don’t love all of Tarkovsky equally. Mirror and Stalker feel alive to me. Nostalghia does not. Likewise, I don’t need constant action, but I do need movement—emotional, philosophical, psychological, narrative. I want to feel that a story is becoming something different from where it began.

That, I think, is the aesthetic I’m really chasing. After that my thoughts wandered to Craig Finn, the singer-songwriter who heads the Hold Steady.

The first Hold Steady song I ever heard was “Sequestered in Memphis.” At the time I misunderstood the entire premise. I thought the narrator was giving an interview to a journalist rather than being questioned by the police. Looking back, it seems obvious, but it never occurred to me then.

What always stayed with me, though, was a single line:

In barlight she looked alright. In daylight she looked desperate.

I’ve know exactly what Craig means here. I’ve been there too.

By then the morning had slipped away from me. As of this writing, I’m still working on my essay, Am I Bisexual? It should probably have been published two days ago. It’s one of the more complicated pieces I’ve written in a while, and I’d rather finish the edit properly than rush it out simply to keep the daily streak alive.

The plan from here is straightforward. I’m going upstairs to keep editing for another hour or two. I’ll get organised, probably grab a short nap later this afternoon, and then head down to southern Osaka in plenty of time to meet Elliott at 6:30.

Everything else can wait.

II. Afternoon

By nine I’d finally stopped putzing about I was about to start. I rearranged the room one more time, put on Neil Halstead instead of Ryan Adams, then Ryan Adams instead of Neil Halstead, opened three browser tabs, closed two of them, looked at hotel dates, thought about escorts for exactly as long as I had promised myself I wouldn’t, and somehow convinced myself this counted as preparation.

It did, in a way. Every writer has their rituals. Mine mostly involve avoiding the sentence I’m about to write.

I remembered a much loved Superchunk lyric:

“So you wanna get out / well I’ll draw you a map.”

This turned out to be the whole morning. Dude if this place sucks so bad just jet. I’ll buy you and Amtrak ticket. Seriously bro. Hit the brinks.^

The next few days existed only as pencil marks: maybe Osaka until Monday, maybe longer, maybe Pattaya, maybe Litz, maybe Hugh, maybe Mio. None of it fixed. Just possible roads branching away from the same hotel room.

The night before, Litz had mentioned how much she loved the ending of piece I wrote about her. I had already mostly forgotten this part, so I took another look. It went like this:

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

I made it halfway through before I started crying. Not dramatic crying. Just enough that I had to stop reading. Sometimes a paragraph waits until you’re ready to understand what you wrote.

III. Early Evening:

Around 6:30 this evening, after working for about an hour and a half on the edit of yesterday’s journal, I walked a few minutes from my new hotel to a nearby convenience store to get something to drink.

Several hours earlier, I had texted my friend Elliott to ask whether he wanted to grab a drink tomorrow night. As I walked to the store, he replied that he was up for it and suggested a beer bar in southern Osaka. I told him I would meet him there.

Thinking about Elliott, I reflected on how much I admire his intelligence. I am a high school teacher, and Elliott used to be one of my colleagues. He left the school years ago and now tutors economics online and manages various investments. He also used to teach mathematics.

I am a social studies teacher. Over the years, I have taught a wide variety of classes, and I feel that I could adequately instruct students in almost any area of social studies. Elliott’s mathematical intelligence, however, has always struck me as remarkable.

In fact, I sometimes envy the mathematics teachers I have known, because mathematics is simply not one of my strengths. I was a decent math student for a time, but I hit the wall with calculus during my junior year of high school and never took another math class. Today, I almost never use mathematics except for the calculator on my phone and a little basic financial housekeeping.

This does not mean that Elliott is smarter than I am. I consider myself highly intelligent. Nonetheless, several times over the years, I have wondered whether he might indeed be smarter than me.

Thinking about it today, I realized that this is probably because his intelligence expresses itself very differently from mine. If I absolutely had to, I could probably relearn enough mathematics to teach middle school. That would be about my limit. Elliott is whip-smart and could probably teach most of the social studies classes I have taught without too much difficulty.

I often reflect on how strongly my intelligence expresses itself in certain areas of life, while in others I am essentially incompetent. I have a solid understanding of subjects such as history, politics, philosophy, psychology, religion, and metaphysics. However, I could not change a tire to save my life.

Although I am not exactly made of money, I almost always call a professional to handle household tasks such as fixing a faucet or clearing a drain. I find these jobs to be a tremendous hassle. In fact, they piss me off. I am happy to pay someone a few dollars to come and sort them out.

As I entered the convenience store, my thoughts turned to the screenwriter Aaron Sorkin. Sorkin is one of the greatest television and film writers of all time. I love The West Wing and The Social Network, and I have enjoyed much of his other work. For reasons of his own, however, Sorkin insists on directing some of his films.

He wrote and directed Molly’s GameMolly’s Game sucks ass. The script is incomprehensible and all over the place. It is, without question, the worst piece of writing he has ever produced. The direction is equally terrible. The characterization is weak, the emotional beats are overdone, and the entire film is syrupy and sappy. I cannot stand it.

A second film of interest here is The Trial of the Chicago 7, which Sorkin also wrote and directed. The script is actually quite good, and the acting is strong. Once again, however, Sorkin’s direction is awful.

The film concerns the protests surrounding the 1968 Democratic National Convention in Chicago. I was not alive at the time, but my understanding is that thousands of protesters gathered in the city, largely in opposition to the Vietnam War and to the Democratic Party’s handling of it. The police responded with tear gas, clubs, arrests, and widespread violence. Some protesters fought back, and things became extremely ugly.

There are only a few major action sequences in the movie. Sorkin’s handling of them is pure trash. He has no idea how to direct physical chaos. The cameras are always in the wrong place. It is difficult to tell where anyone is or what is happening. The entire thing feels out of control, and not in an intentional way.

Molly’s Game is a bad movie, and I do not care. The Trial of the Chicago 7 could have been a good movie with competent direction. Sorkin was simply not the man for the job.

As I walked back to my hotel, I began thinking about how strange it is that otherwise intelligent people, for reasons of ego, ambition, or simple misjudgment, sometimes insist on doing things at which they are obviously bad.

Then I thought: Well, I have probably done this too.

There have certainly been times when I believed I could handle something and ended up over my skis. I suspect this is true of everyone. We all have strengths and weaknesses, and intelligence manifests itself in different ways.

Over time, I have tried to learn how to pick my spots and stay in my lane. I do not always succeed. However, I hope I do a better job of it than Aaron Sorkin.

IV: Evening Back at My Hotel

As I walked to the train station to go meet Elliot I called Annie. Annie has always been completely outta control, and she absolutely loves it. Within five minutes she’d decided to crash her ex-husband’s wedding in a tent, seduce one of the guests, reminisced about working at Spokane’s Mars Casino, told me stories involving cocaine, dresses, gambling, and an older gay man who’d taught her “everything about sex,” invited me to her hypothetical future wedding, and, after I jokingly suggested we skip straight to sex ourselves, said she’d think about it. Talking to Annie has always been like standing beside a fire hose. The stories don’t really have beginnings or endings. They simply arrive.

The morning passed quietly. I answered a message from my brother Hugh, who was planning to stop by the house in Kyoto sometime during the coming week, and sent a few encouraging replies to several women I’d been chatting with online. One woman in the Philippines was hoping to find work overseas in Singapore or Malaysia. Another, somewhere in Thailand, simply wanted to know how my morning was going. Others had drifted into that peculiar limbo occupied by most dating-app conversations: friendly enough to continue, but unlikely ever to become anything more.

After a while I found myself scrolling through far more conversations than I probably should have. Dating apps create the illusion that your social world is constantly expanding, when in reality most interactions simply fade away after a few messages. Every now and then somebody surprises you, but most conversations end not with an argument or rejection, but with simple inertia. Nobody does anything wrong. Life just moves on.

Perhaps that’s why I no longer find the process frustrating. Years ago I probably would have chased every lead, replied to every message immediately, and wondered why nothing seemed to develop. These days I treat it more like browsing a bookstore than shopping for groceries. If something genuinely interesting appears, wonderful. If not, I’ll probably enjoy my coffee just as much.

My musical companion for the morning was Craig Finn. I first discovered him through “Sequestered in Memphis,” and, like many first-time listeners, completely misunderstood the song. I thought the narrator was speaking to a journalist after a reckless night in Memphis. Only later did I realize he was being questioned by the police. Somehow that misunderstanding didn’t lessen the song; if anything, it made me appreciate Finn’s writing even more. His characters are so vividly drawn that they feel real even when you’ve misunderstood the plot.

One line has always stayed with me: “In bar light she looked alright. In daylight she looked desperate.” Finn is ostensibly describing someone else, but the brilliance of the lyric is that it cuts both ways. By dawn, they’re both desperate. We’ve all had moments where the previous night’s confidence evaporates with the morning light. Finn simply found the perfect sentence to describe it.

V: On the Way to See Elliot

After finally giving up on the day’s editing, I showered, threw on a clean shirt, and hurried toward Taishō, where I was meeting Elliott at a craft beer pub called TNT. I was running a few minutes behind schedule—as usual—but Elliott has never struck me as the sort of person who minds waiting over a pint. I figured I’d make up the time somewhere between the hotel and the station, although experience suggested otherwise.

The train ride became one of those familiar periods of suspended possibility. While checking directions and changing lines, I also found myself checking dating apps, replying to messages, and idly wondering what the rest of the evening might bring. If everything went perfectly, I’d spend a few hours drinking good beer with Elliott, head back toward my hotel, and perhaps finish the night with a date. It wasn’t exactly a plan so much as several loosely connected possibilities competing for my attention.

Somewhere between stations my thoughts drifted to Tomoyo, one of my former students whom I’d seen again at the book launch. We’d nearly gone out together once before, years after she’d graduated, but circumstances had gotten in the way. Twenty years have now passed since I first taught her, which removes any ethical hesitation I might once have felt. I found myself wondering whether I should simply ask her out the next time I am in Tokyo. Sometimes life becomes unnecessarily complicated because we spend too much time calculating the odds instead of asking straightforward questions.

That seemed to be the theme of the journey. I checked my bank balance, priced a few possibilities for later that evening, briefly reconsidered future trips to Thailand and even South Korea, nearly walked the wrong way through a station, and at one point came within a few feet of being clipped by a taxi while jaywalking. None of it mattered very much. My mind was simply ricocheting from one possibility to another while my body steadily carried me toward a beer with a friend.

By the time I emerged from Taishō Station, the mental static had largely disappeared. Elliott was waiting, the pub was less than a minute away, and for the next few hours the only decision I intended to make was which beer to order first.

=====

The Osaka Loop Line has a hypnotic quality after a while. Every minute or two another calm recorded voice announces the next station, another transfer, another reminder to mind the gap. After ten or fifteen minutes the words stop meaning anything. They become part of the rhythm of the journey, almost musical, drifting in and out beneath whatever happens to be occupying your thoughts.

Mine, for reasons I still can’t explain, wandered toward negative igloos.

I have absolutely no idea what a negative igloo is. I have never knowingly encountered one before or since. It arrived fully formed, demanded my attention for perhaps fifteen seconds, and then disappeared forever, leaving me no wiser than before. If someone were to ask me today what a negative igloo might actually be, I honestly couldn’t begin to answer. Nonetheless, somewhere between Kitahama and Taishō, negative igloos briefly became the most important concept in my universe.

The rest of my brain was scarcely more coherent. Ryan Adams was singing Drank Like a River, and I found myself thinking about the tiny crack in his voice—that moment where it sounds less like he’s performing a song than remembering something he’d rather forget. Some singers sound polished. Ryan often sounds wounded. There’s a difference, and it’s one of the reasons I keep returning to his records.

Then, just as suddenly, I realized I had absolutely no idea where I was.

I’d somehow missed my stop, wandered out the wrong exit, and was now standing in a station that looked vaguely familiar while possessing almost no useful geographical knowledge whatsoever. Google Maps insisted I was only two minutes away from Elliott. My instincts insisted otherwise. My instincts, it should be noted, have an unfortunate habit of arguing with Google.

For a few minutes I experienced what I can only describe as a minor travel panic. Not real panic—nothing so dramatic—but that familiar sensation every traveller knows, where every street begins to resemble every other street and every directional arrow seems specifically designed to send you somewhere else. I walked one way, doubled back, checked Google again, ignored Google, trusted Google, ignored it again, and somehow managed to end up exactly where I’d started.

Meanwhile my thoughts continued their usual pinball routine. Was the Sony credit card finally on its way? Should I spend part of August in South Korea instead of Bali? Would Yo still be available later that evening? Why hadn’t Jennifer replied? Why did Meinster have time to send me promotional emails but apparently not royalty statements? None of these questions had anything whatsoever to do with finding a pub in Taishō, but my mind saw no reason to separate one subject from another.

Eventually I admitted defeat and messaged Elliott. Dude I am totally lost. His reply arrived almost immediately.

Where are you?

It was the perfect question because I genuinely didn’t know.

Google claimed I was standing practically on top of TNT Craft Beer Pub. My own eyes suggested I was standing outside an Irish bar that definitely wasn’t TNT. For a brief moment I began to wonder whether the pub existed only as a cartographical rumour.

I texted him back and said I was looking at Taisho Station. He said he would be right there. One minute later I saw him across the street and crossed to meet him.

When Elliott finally rescued me from my navigational incompetence, TNT turned out to be exactly where Google had insisted it was all along. The fault, as usual, lay somewhere between the phone and the human operating it.

“You’re hopeless,” he said.

“I prefer ‘geographically imaginative.'”

He laughed. “Come on.”

One minute later we were golden.

VI: TNT Craft Beer with Elliot

The pub was everything I hoped it would be: a long wooden bar, a dozen taps of rotating local craft beers, a cheerful bartender in a baseball cap who somehow managed to keep everybody’s glass full without ever looking hurried. When one of the kegs kicked halfway through pouring my pint, she apologized and handed me the remainder for free.

“Sorry” she said.

“No worries,” I said. “I’ll always take half a beer for free.”

She laughed.

“I like your hat,” I said.

“I get that a lot,” she said.

I turned to Elliot and asked if he wanted to hear a joke.

“A shepherd is in bed with his girlfriend for the first time. She asks him, ‘How experienced are you?’ He closes his eyes…starts counting…and falls asleep.”

The bartender laughed.

Elliott buried his face in his hands.

“Please,” he said, “never change.”

“I make no promises” I said.

By the time the quizmaster welcomed everyone, we’d accumulated enough empty glasses to suggest we were taking the evening seriously while simultaneously possessing almost no confidence in our ability to answer questions about anything.

“What’s are name?” Elliot asked me.

“How about the Glorious Mofos?”

“Of course.”

“Ladies and gentlemen,” the quizmaster announced, “welcome!”

“He seems enthusiastic,” I whispered.

“He’s paid to be.”

We were spectacularly mediocre.

Spain had won something. Bananas were radioactive. Kobe Bryant was apparently named after Japanese beef. Beyond that we entered a sort of intellectual free fall.

“What do you think?”

“No idea.”

“You?”

“Less than no idea.”

“Write banana.”

“I already did.”

“Excellent.”

Our strategy rapidly evolved into letting Elliott answer the questions that sounded plausible while I concentrated on drinking beer, admiring the bartender, and periodically checking whether Yo had confirmed our appointment.

At one point Elliott looked over my shoulder.

“You’re really going after this?”

“I think so.”

“You ever think about…you know…not?”

I considered that.

“For about three seconds.”

He laughed.

“I thought so.”

That was one of the things I’d always appreciated about Elliott. He never judges. He asked questions. Usually he agrees with me. Other times now. Occasionally he looks at me as though I’ve completely lost my mind. But whatever I do he never tries to become my conscience. Old friendships eventually settle into that rhythm. You stop trying to improve each other and simply learn to enjoy each other’s company.

The conversation drifted from Japan to Canada, from the weather to my girlfriends, from travel plans to parents. I vented a little about my mother bitching about my writing. Elliott listened more than he spoke, occasionally nodding, occasionally smiling in that understated Canadian way that somehow communicated, I don’t entirely agree, but I understand why you’re upset.

By the time the second round ended, I’d glanced at my watch three or four times.

“You’ve got somewhere to be,” Elliott said.

“I might.”

“You definitely do.”

“Indeed I do.”

He grinned.

“Go lose your T-card.”

I laughed so hard I nearly spilled my beer.

“I’ll report back.”

“You’d better.”

We settled the bill, shook hands outside TNT, and headed in opposite directions. Elliott toward another ordinary Saturday night. Me toward Umeda, where Yo-chan was waiting.

VII: On the Way to See Yo Chan

As I entered Taisho Station the JR announcements began their familiar chant once again.

The next stop is…

Somewhere between stations my mind wandered back to negative igloos. I still have absolutely no idea what one is.

The JR announcer continued serenely informing us that the next stop was Kyobashi, or Osaka Castle Park, or somewhere that probably existed. In my head it became:

“Please enjoy negative igloos. Transfer here for the glorious nonsense line. Please exit on the right.”

“Yeah, yeah,” I muttered. “I got it.”

I did not, in fact, have it.

Somewhere between the craft beer and the heat, I’d managed to convince myself I’d fallen asleep on the train. Maybe I had. Maybe I hadn’t. Either way, I suddenly had absolutely no idea where I was.

Oh, shit.

I checked Google Maps again. Every time I opened it, it confidently gave me a different answer.

“Seventeen minutes.”

I calculated that I would get to the shop about five minutes early. This turned out to be off. The announcer cheerfully reminded us to mind the gap.

“I’m trying to mind all the gaps.”

I got off the train and looked around. Then decided getting off had been exactly the right decision. I checked the train map on the station board. I was also seventeen minutes past Umeda. Oh great. Back we go.

I thought to myself: I need cash. Then a taxi. Then a cigarette. Possibly in that order. First I had to get back to Umeda.

The train came and I rode the short distance back. The instant I stepped onto the street, I lit a cigarette and hailed a cab. I had just a fee drags when a cab pulled up and I had to toss the cig.

The taxi driver nodded when I said, “Umeda.” Progress. Seven minutes, Google claimed. For once, we agreed. As the cab rolled through the humid Osaka evening, I realized I was no longer worried about getting lost. I was worried cause I was a little late.

I’d spent the entire afternoon imagining meeting Yo chan, and now my grand entrance was shaping up to be me arriving slightly sweaty, smelling faintly of cigarettes and carrying too little cash.

Great first impression I thought.

The driver dropped me exactly where Google said he would. Google immediately betrayed me again.

Fourth floor. I found the fourth floor. Everything was locked. No people. No reception. No Yo-chan. No nothing.

Just an eerily quiet hallway that felt like the set of a film where everyone had disappeared moments before I arrived.

I called the shop.

“I’m here.”

A reply came back almost instantly.

“First floor. It’s hard to find.”

No shit.

A guy walked over and picked me up. We walked five minutes to where the shop really was, no where near where Google said it was. Typical. This guy knows nothing. Apparently.

Five minutes later I found the place.

VIII: Yo Chan

The shop staff took me up in the elevator to the 7th and opened the door to room 701. For some reason I found this number to be fitting. There was a shower but no sink. I took my own clothes and began to rinse off. Yo chan soon entered the room. She looked like her picture, but not quite. The agency website said she 24, a fact she confirmed in person. She looked about 28 to me, and I supposed her life was perhaps not the easiest.

I found her attractive, and knew I would be able to cum. She joined me in the shower, soaped up, and began to stroke my dick. In general, I prefer to handle my equipment. It is a sensitive area, and I just know it best. I turned my back to her, and then a minute later I stepped out and toweled off. She followed shortly thereafter.

As we stepped out of the shower, she assessed my naked body. She said, “You look like Boris Johnson.” I laughed away and didn’t reply. I decided then that there were some conversations not worth extending.

We climbed onto to bed. I was already erect, and she was at half mast. She unwrapped a condom and slid it on my dick. I had never sucked anyone’s dick before, and I was both exited and just a little nervous.

We began kissing. I like a bit of tongue during kissing, however, her tongue was a little aggressive. Oh well I thought, kissing, at least tonight, would not the main event. I broke the kiss, and went down on her. She was semi-erect, however I was able to fit her full penis into my mouth. The first thing I noticed was her large foreskin. The second thing was, the act was neither pleasant nor unpleasant, and she tasted neither good nor bad. I was eager to make her cum.

After a bit, she motioned for me to come back up to the head of the bed. She climbed back on top of me, and slid my dick into her ass. She had applied lube to her asshole, and hard dick slid in easily. After a short amount of time, I asked her to turn around and entered her from the rear. She began to moan and pant, and I found this very sexy. I was about to cum, and then, as I usually, do, I pulled and finished on a towel while sitting on my knees.

I then collapsed back the bed. She also sat on her knees, and came on the towel. Some of her cum landed on my leg, which I found faintly amusing. After this, I needed a cigarette. There was no smoking in the room so I asked her if I could go downstairs. She said sure, just pick me up a Pocari Sweat and call reception to get back up. I told her I would be back in five minutes, however I knew this was a lie. The fact was I would smoke three of four cigarettes and decompress for a while. This was about an hour into our date, and I had paid for ninety minutes. I did not want to re-engage in sex, so smoking and thinking quietly seemed like a good plan.

When I stepped back onto the street, the wind had gone out of my sails. Not in a bad way. Just…gone. For most of the day I’d been propelled by anticipation. Catch the train. Find Elliott. Don’t get lost. Meet Yo chan. Get the cash. Find the building. Try not to make an idiot of yourself. Then, just like that, there was nothing left to chase.

Osaka was still humming around me, but I’d become a spectator again. I checked the time on my phone. It was 12:30 AM. This immediately made me think of the Katheryn Bigalow film Zero Dark Thirty. I found myself thinking about Zero Dark Thirty. I’d never understood the criticism that it somehow endorsed torture. Showing something ugly isn’t the same as celebrating it. A film can portray violence honestly without recommending it, just as Goodfellas isn’t an argument for joining the Mafia. Sometimes a story simply trusts the audience to tell the difference.

I ducked into a nearby convenience store and bought two Pocaris, two beers, a burrito, and a pack of pack of cigarettes. I smoke another heater and drank one of the beers on the street. Then I called up to reception. There was no security, and I did not see any other customers the whole time I was there, however, at least time, I did what I was told.

Back in bed with Yo, we both undressed again and she fell asleep. I found our legs entwined. He body was very comfortable, and I can honestly say this was the sweetest part of the evening.

She woke up and pointed at the clock. It was time to go. We dressed and walked to the elevator. I leaned to give her a goodnight kiss, and she kissed me back, lightly. This was goodbye.

=====

It was after last train, so I got a taxi back my hotel near Yodoyabashi Station. The taxi rolled silently through the warm Osaka night I leaned my head against the window and watched the city slide by. Tomorrow I’d probably throw myself into another impossible plan, another train, another woman, another glorious and bizarre day. I was, by this point, quite tired.

A few hours earlier I’d been arguing with Google Maps, inventing negative igloos, convincing myself I’d missed stations that probably never existed, and experiencing a full-blown case of what I can only describe as travel boggle. Now all that urgency seemed faintly ridiculous. The date had happened. It had gone OK. I lost my T-card. I’d survived.

Travel does that. What feels catastrophic at eight o’clock becomes a mildly amusing anecdote by twelve-thirty.

But for the moment, there was nowhere I needed to be.

IX: Late Night Hotel and Bed

Back in my room I took off my shirt, washed up, and prepared for bed. For reasons I can’t entirely explain, my thoughts eventually wandered toward football. I’ve always enjoyed the sport, even if basketball remains my first love, and one of my earliest football memories comes from a Washington State game against Stanford. My mother, Claudia—CL to longtime readers—was friendly with Janet Elway, John’s mother, and at one point Janet served as something of a mentor to her. Through that connection, we ended up at the game while John Elway was still Stanford’s quarterback.

Before kickoff, Elway apparently told my mother that if he threw a touchdown, he would point toward us in the stands. Naturally, he did throw one. He was John Elway, after all. And after the score, he looked up and pointed in our direction while we yelled ourselves hoarse. I was still rooting for Washington State, which complicated the moment slightly, but even then I understood that we were watching somebody exceptional.

Elway went on to become one of the defining quarterbacks of his generation, first at Stanford and then during a long NFL career with Denver. What stays with me, though, isn’t the statistics or the championships. It’s the strange intimacy of that afternoon: my mother’s connection to his family, the promise made before the game, and the tiny gesture toward the stands after the touchdown. Sports are full of enormous public moments, but the memories that survive are often the small private ones folded inside them.

I claimed into bed, and indulged in one final reflection for the day. I thought about how funny it was that one minute you are deep in the throes of passion, moaning and panting your partner’s name, and the next you are smoking a cigarette, drinking a beer, and thinking about Zero Dark Thirty on the street. Sex, which feels so wonderful and necessary at the time, does tend to recede pretty quickly. However, the power of good sex, as Kevin Drew says in out epigraph, cannot be beat.

Dedication:

For Yo chan. Thank you for taking my T card baby. Godspeed. You rule.

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. And also, nobody shushes my boy.

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.

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: 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.

On Larry King, the Radio GOAT

Epigraph:

“I listened to the radio / I waited all night long…”
— Radio Radio, Elvis Costello

Note: This piece reflects my personal memories of listening to Larry King’s overnight radio show in the late 1980s and early 1990s, along with later impressions from television appearances, interviews, and conversations with people who knew him. It is written in the spirit of appreciation and nostalgia rather than media criticism, and emphasizes the uniquely loose, humane, and unpredictable quality of King’s radio work, which for me remains the defining core of his legacy.

I grew up listening to Larry King’s overnight radio show between roughly 1988 and 1992, and in my opinion — which happens to be correct — the radio show was much better than the television version that later made him famous. The TV show was good, even great at times, but radio was longer, looser, freer, and far more unpredictable. It had weird guests, weirder callers, and the feeling that anything might happen at two in the morning. That’s where Larry really lived.

I would listen in my bedroom at my parents’ house in Spokane, Washington, the volume turned low, the house quiet, insomnia hovering. The Spokane AM station — KGA 1510 — carried the show from around 9 PM Pacific time, and then, wonderfully, they would run it again. So I’d listen from nine to midnight, fade, wake at two or three, and hear the same segment again in a half-dream. The effect was surreal. Didn’t I just hear that caller? Didn’t Larry just say that? It created a strange loop of late-night déjà vu that only made the whole thing more atmospheric. The show felt less like programming and more like a continuous nocturnal conversation.

My friend Kelly Rudd loved Larry too. When we were in high school we were both big fans of the radio show, and we talked about it constantly. There were a couple of things that we especially liked. The first was that Larry famously did no preparation. He knew a huge amount about the world, of course, but he didn’t read guests’ books ahead of time. He wanted to come in cold. If his guest was a firefighter, he’d ask, “So what’s it like to be a firefighter?” It sounds lazy, but it was brilliant. By staying open and getting out of the way, he let the conversation go anywhere. This way the show became eventful.

Another thing we loved was what happened after the guest left. Larry would open the lines and take questions about absolutely anything. Most of the time he was generous and patient, but when callers went off the rails he had a signature phrase. He’d cut them off gently: “Cold compress, ma’am,” or “Cold compress, sir.” Basically: lie down, ice your head, regroup. It was hysterical, especially because he used it sparingly. When “cold compress” dropped, you knew things had gotten weird.

Anyway, Kelly and I loved Larry so much that when the station suddenly dropped the show, Kelly proposed we drive to the radio station and protest. So we skipped school, drove across town, and rang the intercom demanding to speak to someone about the cancellation. The station manager eventually came down and heard us out. We knew we weren’t changing anything, but it felt right to try. Larry never came back to Spokane radio, and the show faded not long after, but the whole episode captured what the show meant to us. It wasn’t just background noise. It felt alive.

Larry’s on-air style was the key. He was unbelievably relaxed. By the late ’80s you could tell he had done thousands of hours. Nothing fazed him. Weird guests, drunk callers, eccentrics — all the same to Larry. He absorbed everything. He had pet phrases — “cold compress” chief among them — and he deployed them like a veteran reliever, only when needed. He famously did no prep, and he leaned into naïve questions. He’d ask something simple and let the guest do the work. The effect was disarming. People opened up. He also had real humanity. He listened. He didn’t mock callers. He didn’t rush them. There was compassion there, and I think that’s what I loved most.

And the show could get wonderfully out of control. In one story Larry told from his old Miami days, an adult actress he was interviewing suggested they just have sex during the commercial break. Larry, amused, asked the producers to clear out — but there wasn’t enough time. That kind of anecdote captures the looseness of late-night radio. It wasn’t polished. It was alive.

Larry left the overnight Mutual Radio show in 1994 to focus on television. By then I had already drifted away, but I still caught Larry King Live on CNN over the years. I remember watching during the O. J. Simpson trial while at Otago University in New Zealand, when the show became part of the nightly noise. Later there were the Vladimir Putin interviews — classic Larry, conversational and oddly disarming. And of course there were the great comic moments, like the interview with Jerry Seinfeld where Larry suggested the show had been canceled and Seinfeld snapped back in disbelief, and the Norm Macdonald appearance where Norm kept repeating, “I’m a deeply closeted homosexual,” and Larry tried earnestly to parse it. “So that means you’re gay?” “No, Larry,” Norm replied, “it means I’m deeply closeted.” Pure Larry: sincere confusion meeting absurdist comedy.

Larry’s personal life was famously complicated. He married eight times, had several children — including sons Chance and Cannon later in life — and lived in a kind of perpetual romantic improvisation. The marriages came and went. The last ended painfully and publicly. He once joked he’d never leave his wife unless Angie Dickinson came along — and when she did, he married her. That was Larry: impulsive, affectionate, slightly chaotic. Despite decades of success, he didn’t leave the kind of massive fortune people assumed. The money came and went, as did the marriages. It was a life lived in motion.

My friend Sergio Mandiola actually knew Larry in his later years in Los Angeles. Sergio was running an independent studies program at Beverly Hills High School, and Larry’s sons Cannon and Chance, and he taught his sons for three years. Larry would come by for open nights or just to chat.

Sergio Mandiola: “Larry would come in from time to time and we would talk. He was lovely and open. He talked about his family and his career. One time he told me, ‘Sergio, you should totally have a radio show!’ I was flattered. One thing about Larry is his politics were more to the left than he let on on air. He had strong views and wasn’t afraid to share them in person. Larry was a true mensch and I’m glad I got to spend time with him. I miss him.”

In the end, I’ll say it plainly: for me, Larry King is the radio GOAT. There was no one like him, and there probably never will be. It wasn’t just longevity. It was the curiosity, the looseness, the humanity, the love of people, politics, baseball, and life. He trusted the conversation. He let the night unfold.

And then there was that absurd, wonderful USA Today column, which read like a diary gone completely outta control. Mets lose 6–4…Rain in Baltimore…Clinton flies to Ireland…You’d read it and think, Larry, baby, WTF is this? And also, Mr. USA Today, WTAF are you doing paying for this? But somehow it worked. It was pure Larry — fragmentary, observational, intimate.

And that’s how I remember him most clearly: late nights in high school, the radio turned low, insomnia hanging in the room, Spokane quiet outside.. Sometimes I’d listen from nine to midnight, fade, then wake again to the rerun, half-dreaming, half-aware, caught in that strange déjà vu — didn’t I just hear this? — while Larry kept talking, calm as ever, taking calls from truckers and insomniacs and eccentrics. My listening years were brief, but they stuck. And when I think of Larry now, that’s where I go back to: the low hum of AM radio, the half-fade, and the sweet sounds of his voice in my ear.

Dedication:

For the one and only GOAT, Larry Motherfucking King. RIP baby.