Posted on by Matt Thomas

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.

Posted on by Matt Thomas

Don’t Pump Me Man!

Note: Spokane, early 1983: minor league baseball, cheap seats, and kids living in the gaps between innings. This piece recalls Spokane Indians games, chasing balls during batting practice, and a strange collision of childhood mischief and adult volatility at the edge of the outfield fence. Sandy Alomar Jr.—then a local catcher on his way to a long MLB career—signs a baseball in handwriting so precise it feels like a signature on a future already underway, while a moment of chaos involving thrown persimmons and a furious adult named Mike Trowbridge becomes the kind of story that sticks far longer than the season itself.

Epigraph:

Do you know who you’re fucking with?/ You’re fucking with a stallion mange.

Ween

It was 1983 in Spokane, the kind of summer that felt permanently suspended in late light and dry heat, where the air at night still carried the dust of the day like it had nowhere else to go. We played Little League baseball in uniforms that never quite fit right, and then on weekends we graduated to something bigger and looser and more important: Spokane Indians games at the old stadium, Single A ball, where the dreams were real and still close enough to touch.

The Spokane Indians were a kind of civic promise back then. It was a small town, and in the early 1980s there wasn’t always a lot going on. The Indians were not quite big league, but not quite nothing. Just enough baseball to make you believe that something important was always one bus ride away. The seats were cheap, the beer cheaper, and the fences closer than they should have been. The whole place had that slightly improvised feel—like the city had built it thinking, this will do for now.

We didn’t go to games like spectators. We went like we belonged.

Behind the outfield wall during batting practice, kids gathered like scavengers. We chased homers, argued over balls, sprinted through patches of grass worn down by repetition. Sometimes we were the only ones back there. Sometimes there were older kids, or dads, or random locals who knew the angles better than we did. It was a loose territory. Not quite policed. Not quite ours. Something in between.

That summer, the Indians had a catcher everyone knew. Local kid. Quiet confidence. Clean mechanics. The kind of player adults already talked about like he had a future attached to him.

Sandy Alomar Jr. was that guy even then—before the long MLB career, before the All-Star years, before anyone outside Spokane would know the name properly. He was already different. You could see it in the way he stood when he wasn’t moving, like he was always half a second ahead of the next pitch.

I got his autograph once. It wasn’t dramatic. Just a moment after BP, when he signed a ball for a cluster of kids leaning too far over a rail. His handwriting was unexpectedly beautiful—controlled, deliberate, almost elegant in a way that didn’t match the dirt and sweat of the field. I remember thinking even then: this is what someone looks like when they’re going somewhere.

I kept that ball for years.

Because baseball wasn’t just baseball. It was a hierarchy you could see. You had the guys who were going to make it, the guys who might make it, and the rest of us orbiting the idea that proximity alone might transfer something.

Most of them wouldn’t go anywhere. That was obvious even then, though nobody said it out loud. But that day, none of that mattered yet. What mattered was the fence.

Our party was up high in the stands on the first base side, just beyond where the stadium fence met a thin strip of wild space. A tree had grown there—some kind of fruit tree, nobody was ever fully sure what it was. Persimmons, maybe. Something orange-red and heavy-looking, the kind of fruit that doesn’t look like it should be thrown but absolutely is.

Some kids started throwing them. Just kids, just fucking around. But they didn’t know who they were fucking with. Fuck with me and I’ll fuck with you.

The fruit flew. Not carefully. Not aimlessly either. More like experimentation. Testing distance. Testing reactions. Some of them were aiming at fans, others just launching them over the fence because it felt like something you could do if no one stopped you.

It was mildly funny at first. Then mildly annoying. Then mildly dangerous in a way that nobody fully acknowledged.

Because persimmons, if that’s what they were, aren’t soft. They hit like small decisions.

I remember one bouncing near a row of seats and rolling under a foot. Someone laughed. Someone else shouted. But nobody moved with urgency yet. It was still in the category of “kids being kids.”

Until Mike Trowbridge noticed.

Mike T was there with his kids—David Trowbridge and his sister Dawn. David had been a teammate of mine in Little League, a few years younger, outfield guy, quiet in the way younger kids sometimes are when they’re still deciding how loud they’re allowed to be. Dawn was just there in the background of everything, observing.

Their dad, Mike, was not background.

He was one of those adults you noticed before you understood why. Volatile energy. Tight posture. Goatee, black tank top, gold chains around his neck. A bit of a greaser; drove a Harley. Always slightly too close to losing his temper. He wasn’t a bad guy exactly—he could laugh, he could talk—but you always felt like there was a second version of him sitting just under the surface.

He saw the fruit being thrown. And something in him snapped into motion. He walked straight to the fence line, fast enough that it changed the temperature of the moment.

“Knock that shit off right now,” he yelled.

The kids paused. Not because they were scared exactly, but because the voice had weight.

Then one of them—small kid, maybe ten, sunburned confidence, the kind of kid who doesn’t fully understand consequences yet—looked up and said:

“Don’t pump me, man.”

It was such a strange sentence. Too casual for the situation. Too confident for the speaker. Like he had borrowed it from somewhere older and wasn’t sure how it fit yet.

There was a beat of silence where the entire stadium noise seemed to pull back slightly.

Mike T looked at him.

“Don’t pump me?” he said.

Then his voice shifted.

“You want me to pump you? I’ll pump you.”

And in that moment—this is the part that still feels unreal even now—he climbed the fence. Not slowly. Not theatrically. Just decisively. Like the boundary wasn’t a boundary at all.

Everything changed at once.

Me, David, Dawn—everyone nearby—we all froze in that wide-eyed way kids do when they realize the rules might not hold. It wasn’t comedy anymore. It wasn’t baseball anymore.

It was just: Mikey baby don’t kill that kid.

That’s what it felt like in my head. Not words were spoken, just panic translated into something almost verbal.

The kids scattered instantly. Full sprint. No hesitation. The fruit stopped mid-air and dropped forgotten. The stadium behind us suddenly felt far away, like it belonged to a different scene entirely.

Mike T took a step forward, still inside the fenced edge of this improvised battlefield, breathing hard, still locked in that strange overlap between anger and disbelief.

And then—somehow—it was over. No actual violence. No contact. Just the threat of it, large enough to erase the mischief that had caused it.

The kids were gone. The fruit stopped flying. The tree stood there like nothing had happened. Afterwards, the stadium noise came back slowly, like a system rebooting.

My dad, Ross, had seen the whole thing. He was laughing, hard. Not the kind of polite laugh adults do when they think they’re supposed to. This was involuntary. Almost helpless. The kind of laugh that tries to stay respectful but can’t quite hold the line.

Because it was funny. In that terrible, chaotic way childhood sometimes is when it brushes up against adult intensity and survives without breaking.

Ross would tell that story for years after. The kid. The fence. The persimmons. The line: don’t pump me man. He never stopped laughing at that part.

Neither did I.

But at the time, I just stood there thinking about Sandy Alomar Jr. somewhere on that field, already on his way to something else entirely, signing baseballs in beautiful handwriting, while right behind the stadium wall the rest of us were learning the difference between games and consequences in real time.

Most of us wouldn’t make it to the Bigs. But for one afternoon in 1983, it all felt like it might matter just the same.was 1983 in Spokane, the kind of summer that felt permanently suspended in late light and dry heat, where the air at night still carried the dust of the day like it had nowhere else to go.

But for one afternoon in 1983, it all felt like it might matter just the same.

Dedication:

For Mike T. And for the kid. You got balls young man, I’ll say that.

Posted on by Matt Thomas

Scenes from Hamilton College IV: Sophomore Year II: The Sports Show, Ann, Getting Fired

Note: This is Part IV of the Hamilton series. Part I, Part II and Part III are available. This post will take up my friendship with Ann, the Sports Show John Innes and friends had, and losing my job at the print short.

I was living in the delta
Wasting most of my time

Car Seat Headrest

I mentioned in Part III that I was on a sports talk show on the college radio station, WHCL. This was called Sports Corner. John Innes was the leader; it was his show. A friend of ours called Jeff Kingsley was on the show, as well as myself. Kingsley was a huge Buffalo Bills fan, and he stayed on top of the sports news, especially the NFL. Innes was always super prepared, and taped the shows which he would later play for his dad when we got back to Washington State. I sort of kept up with the sports scene, but I was mostly there for comic relief. I would crack jokes and make fun of stuff, but was definitely the third banana on the show.

The radio station didn’t have a lot of bandwidth so the listeners were mostly on campus and Clinton locals, but I recall Sports Corner having a number of regular listeners who would call in. From my point of view, the callers were the best part of the show. We treasured our listeners and gave them plenty of airtime. I never told any of them to “cold compress ma’am.” I was a regular as a sophomore and the first half of junior year until I went abroad to New Zealand. When I came back as a senior I think I just guested. I remember one show where Innes asked me what kind of sports were big in New Zealand. I said “marbles, marbles are really big.” I was just fucking around, but it was pretty funny. Although I was only marginally prepared, Sports Corner was a blast and Innes was a great host. He totally could have done it professionally.

I also talked in Part III about Ann. Ann was Ian’s girlfriend sophomore year, and I got to know her pretty well. Ann sort of took over where Rochelle left off in the mothering department, but she was really different from Rochelle. More intense. Ann didn’t like smoking and she tried to stop me from doing so, to no effect. I remember once, I think it was junior year actually, where at a dorm party she grabbed my cigarette from me and threw it out the window. I just shrugged and lit another one.

If Ann was intense, she thought I was. Innes and Ann and I were hanging out once and Innes said “M.A. (that was my nickname at college) is the chillest guy I know,” and Ann replied “I think he is the most intense.” Well, someone will maybe eventually get to the bottom of that one. One day I dropped by Ann’s room and there was a big jigsaw puzzle partially done. I started picking at it, and she stopped me. “That’s for me and Ian,” she said. Must have been some puzzle. Another time I went to Ann’s house with Ian and she tried, I guess, to pair me up with one of her friends. This wasn’t going to take, but we all did sleep, clothed, in the same bed that night. I don’t think I got a lot of sleep.

While some friends came and went at Hamilton, Ann I was close to sophomore, junior and senior year. After graduation she moved to the U.K. for a bit. I wrote about this elsewhere and will reprint it here.

“My friend Ann from Hamilton College went to England after graduation and she and I exchanged a few letters, back when people still wrote letters. She wrote me that she was drinking some, so I wrote a poem about my image of her over there. The original poem had two or three more verses, but they were terrible. Then a little while back I reconnected with Ann, which was great, and re-worked the poem, which wasn’t. It might have been a little better, but it was still bad. These two stanzas, on the other hand, are awesome, and maybe that’s all there ever needs to be said about Ann in England, you know?” Here is that poem fragment:

Ann belle princess of the isles
the orbs whisper your name even if you’ve gotten piles
or if you’re on the game

Buxom barmaid or bellicose barfly
begs the inevitable question
booze improves the poet’s eye. but ruins her digestion

I still like it.

Ann has read some of this blog, and even contributed a piece as a guest writer, which is not currently live.

The other big event sophomore year was when Deb fired me. I mentioned that as a freshman I skipped work some, and the next year this pattern was exacerbated. I still had no money, however work was becoming really tough. This was not Deb and Sally’s fault at all–I just couldn’t hack walking all the way up the hill just to collate. Instead, I spent time in the woods jumping off little cliffs and messing around in the late afternoon. No hard feelings; looking back I should have done things differently. I don’t remember exactly when I was fired, but I think it was about two thirds of the way through the year.

That’s it–this is a short one. There are a bunch of other things that may have happened this year or the next, so I’ll cover some of these in my upcoming junior year pieces.

Dedication: For Ann, the belle princess.

to be continued…

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On the Most Outta Control People in History (aka You’re Outta Control!): #1 Keith Rainere

Note: This piece begins a new series, The Most Insane People of All Time (aka You’re Outta Control), which looks at extreme historical and contemporary figures whose behavior, movements, or belief systems veered dramatically beyond the bounds of ordinary reality. The tone is intentionally informal and impressionistic rather than academic, blending biography, cultural memory, and personal reaction. The goal is not exhaustive analysis but a clear read on just how outta control these figures became. This piece takes up the case of Keith Rainere.

Epigraph: 

“Out of control / You’re out of control…”

— Out of Control, The Rolling Stones

Keith Raniere began life in New York in 1960 and built his early identity around claims of extraordinary intelligence and unusual gifts. He cultivated a reputation as a prodigy, a polymath, and a moral philosopher, though many of these claims were exaggerated or unverifiable. In the 1990s he co-founded a multi-level marketing-style company that ran into legal trouble, then pivoted into what became NXIVM, a self-improvement organization marketed as executive success training. Participants attended workshops, advanced through ranks, and absorbed Raniere’s pseudo-philosophical teachings. He adopted the title “Vanguard,” cultivated an inner circle, and emphasized ethics, discipline, and personal growth. Wealthy backers, including Seagram heiress Clare Bronfman, funded the operation for years, allowing NXIVM to expand in upstate New York and attract professionals, actors, and seekers.

Behind the self-help veneer, however, the structure tightened. Raniere exercised increasing control over followers’ lives, and a secret subgroup known as DOS emerged, involving master–slave hierarchies, collateral-based coercion, and branding rituals incorporating his initials. Superman actress Allison Mack played a key role in recruiting members. Investigative reporting in 2017 exposed the group, leading to arrests. Raniere fled to Mexico, where he was found living in a villa with loyal followers, still holding late-night volleyball sessions and maintaining his guru persona. He was arrested in 2018, returned to the United States, convicted on multiple charges, and sentenced to 120 years in prison. The NXIVM empire collapsed, its mythology dissolving into court transcripts and testimony.

And yet what stands out most about Raniere is not grandeur but pettiness. The volleyball — endless, late-night volleyball as the center of spiritual life — already tells you everything you need to know. Important conversations at midnight on the court, guru hanging out in athletic shorts, disciples orbiting. It has strong George Santos energy: self-invented genius, weird rituals, faux casualness masking control. Then the egomania. The IQ mythology, the titles, the little cushion on stage so he’s physically higher than everyone else. It’s not even theatrical; it’s dreary. The branding scandal — initials burned into skin, coercion, sexual manipulation — pushed it fully into outta control territory. And all of it funded for years by the Bronfman money, which makes the whole thing feel even more surreal. Rich people with nothing better to do underwriting a volleyball cult.

What really kills it, though, is the atmosphere. It’s all so fucking boring. Endless seminars. Faux-ethical language. Guru perched slightly above the group. No charisma, no sweep, just control. I basically hate gurus, and Raniere is the worst kind: small, humorless, self-mythologizing. Even when he fled to Mexico, he didn’t become mythic — he just kept playing volleyball in a villa while the walls closed in. Outta control, yes, but also petty. Not a visionary gone wrong, just an egomaniac running a dreary self-help cult.

By contrast, Jim Jones has a sweeping, almost Shakespearean arc. He began as a Midwestern preacher in Indiana in the 1950s, preaching racial integration and social justice at a time when both were rare in American churches. His Peoples Temple grew steadily, and by the mid-1960s he relocated to Northern California, first to Ukiah and then to San Francisco, where he gained real political influence. The early movement was diverse, activist, and in some respects ahead of its time. But alongside the growth came drugs, paranoia, authoritarian theatrics, and increasing control. Facing scrutiny and defectors, Jones moved followers to an agricultural commune in Guyana — Jonestown — deep in the jungle. Life there deteriorated into long work hours, loudspeaker propaganda, and rehearsals for mass suicide. In November 1978, U.S. Congressman Leo Ryan arrived to investigate, accompanied, improbably, by Mark Lane, the JFK conspiracy lawyer hired by the Temple as a defender. After several members attempted to leave, Ryan and others were shot at a nearby airstrip, and Jones ordered the mass murder-suicide — cyanide-laced drink administered to more than 900 people. The trajectory is horrifying, but it has scale: idealism, power, paranoia, catastrophe. You can at least see how it built.

Marshall Applewhite is stranger still. A former music teacher who fell into an intense partnership with Bonnie Nettles, he constructed a theology blending Christianity, UFO lore, and apocalyptic expectation. After Nettles died, Applewhite grew more isolated and doctrinaire, leading the group known as Heaven’s Gate. Members lived communally, detached from ordinary life, waiting for a spacecraft they believed was trailing the Comet Hale–Bopp. In 1997, Applewhite convinced followers that they needed to leave their bodies to board it. Thirty-nine members died in a coordinated mass suicide in Rancho Santa Fe, California, wearing matching clothing and following a carefully staged sequence. The whole thing is eerie rather than theatrical — calm, methodical, and deeply surreal. Of the three, Applewhite may be the most bonkers, but also the most otherworldly, a teacher who wandered into cosmic delusion.

So the comparison is stark. Jones is tragic and terrifying, a charismatic reformer turned paranoid autocrat. Applewhite is cosmic and surreal, a gentle-seeming teacher convinced salvation lay behind a comet. Raniere, by contrast, is just small — petty control dressed up as philosophy, volleyball instead of vision, branding instead of belief. All three are outta control, but in different registers: tragic, cosmic, and contemptible.

The Most Insane People of All Time (aka You’re Outta Control!): #2 John McAfee
The Most Insane People of All Time: #3 Elizabeth Holmes (aka You’re Outta Control!)
Posted on by Matt Thomas

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.

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On it, Pete

Note: Some stories get better in the telling. This one doesn’t need to. It arrives fully formed—one line, perfectly placed—and has stayed that way ever since. I’ve told it for years and it still lands exactly the same. No embellishment required.

It’s September, 1989.

Two new teachers had just arrived at St. George’s School in Spokane, WA. These are Paul Hogan and Pete Aiken. Paul would go on to have a long and distinguished career, eventually becoming Principal of Jesuit High School in Portland—a major job, the kind that makes a life. I have no idea where Pete is today.

That night, my dad Ross invited them over to the house for dinner. It was one of those late-summer evenings that still carried a little warmth but hinted at the coming turn. Ross was out back at the grill, working over the barbecue with a beer in hand. The adults clustered nearby, talking, drinking, getting to know the new arrivals. There was that particular tone of adult conversation—half-professional, half-social, everyone just slightly aware of roles and impressions.

Out in the yard, it was just the three of us: Pat, Mike, and me. We were playing catch with a tennis ball. Nothing serious. Just throwing it around, loose, casual, the way kids do when the game isn’t really the point. At some point, either Mike or I made a bad throw. It sailed wide of Pat—too far, too high—and rolled past him.

A completely ordinary moment. The kind of thing that happens a hundred times in a backyard, in a summer, in a childhood.

Pat was six. He didn’t chase the ball. He didn’t complain. He didn’t turn to us. Instead, he turned—calmly, deliberately—and looked over at Pete Aiken, one of the brand-new teachers, a guest in our home, a man he had just met. And in a tone of quiet assurance, as if assigning responsibility in a meeting, he just said:

“On it, Pete.”

That was it. No smile. No wink. No awareness of what had just happened. The ball was recovered. The game went on. The adults kept talking. The evening continued. But something had shifted, just slightly, just enough.

Because in that moment, a six-year-old child had somehow crossed the boundary between worlds—between kids and adults, between play and work—and issued a line that did not belong to him, but fit him perfectly.

I don’t remember what happened next. I only remember that line. And I remember that we have been laughing about it ever since.

The On It Pete Blues (Pete’s POV)

I was new to the city, new shirt, new street,

Standing in a backyard trying hard to be discreet,

Ross on the grill and the talk running deep,

Just another first night—then I heard, “On it, Pete.”

I hadn’t been briefed, hadn’t learned the terrain,

Didn’t know the house or the shape of the game,

Just a beer in my hand, trying not to overreach,

Then a six-year-old turned and delegated to Pete.

Now I’ve worked in schools, I’ve handled my share,

Rooms full of noise, moments needing repair,

But nothing quite like that clean little feat—

Being calmly assigned by a kid in bare feet.

No panic, no pause, no doubt in his beat,

Just a glance and a nod—“On it, Pete.”

And the ball got found, and the night rolled on,

But I knew right then something strange had gone on—

In a yard full of voices, one line cut through the heat:

I wasn’t just visiting.

I was on it.

Pete.

Dedication:

For my brother Pat. And for Pete. Just get on it already baby.

Note: If you liked this story you may also like the stories below, which also cover my time at St. George’s High School.

Scenes from St. George’s, Part I: Erosions, First Love, Headmasters
Scenes from St. George’s, Part IV: Mason Anderson’s Seven-Step Method for Picking Up Women
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On Comebacks and Failed Comebacks IV: Muhammad Ali

Note: This essay is the third entry in the series “On Comebacks and Failed Comebacks.” The earlier pieces looked at very different kinds of returns: the moral vindication of Kofi Annan and the small, tactical in-game comebacks engineered by Joe Nash of the Seattle Seahawks.


The story of Muhammad Ali operates on a much larger stage. Ali’s exile from boxing after refusing the Vietnam draft and his eventual return to the championship ranks is one of the most famous comebacks in sports history. But the episode described here—the Los Angeles suicide rescue in 1981—is a smaller and stranger moment.


The event appears to have genuinely occurred, yet it also carries the faint aura of legend that often surrounds Ali’s public life. The champion arrives, speaks to a desperate man at a window, and the crisis resolves itself. It is almost too perfectly aligned with the myth of Muhammad Ali not to raise a few questions about performance, storytelling, and the way public figures sometimes inhabit the roles the world expects them to play.


In that sense the episode captures something essential about Ali’s comeback. By the time his boxing career entered its final chapters, he had become more than an athlete. He had become a figure whose life continually generated stories that felt larger than ordinary events.


Whether one treats the Los Angeles episode as simple heroism, public theater, or some mixture of the two, it remains a fascinating illustration of how Ali’s legend continued to grow long after the great fights were over.

Some comebacks are measured in championships.

Others are measured in stories.

The career of Muhammad Ali contains both. His return to boxing after the long exile of the late 1960s is one of the great sporting comebacks of the twentieth century. Stripped of his title for refusing induction into the Vietnam War, banned from the ring during what should have been his athletic prime, Ali eventually returned to reclaim the heavyweight championship and cement his place as the most famous boxer on earth.

But the Ali comeback is not just about boxing.

Long before the exile and the triumphant return, the story had already begun to take on mythic dimensions. In 1964 a young fighter from Louisville named Cassius Clay stunned the world by defeating Sonny Liston for the heavyweight title. Soon afterward he announced that Cassius Clay was a “slave name” and that he would henceforth be known as Muhammad Ali.

The change was shocking to much of the American public at the time. Ali aligned himself with the Nation of Islam, spoke openly about race and politics, and quickly became one of the most controversial athletes in the country.

Then came the draft.

In 1967 Ali refused induction into the U.S. Army during the Vietnam War. The consequences were immediate and severe. He was stripped of his heavyweight title, banned from boxing, and faced the possibility of prison. For several years the greatest fighter in the world was not allowed to step into the ring.

The exile transformed him.

When Ali eventually returned to boxing in the early 1970s, he was no longer merely a talented heavyweight with a flair for poetry and bravado. He had become something larger: a political figure, a symbol of resistance, a man whose name carried moral and cultural weight far beyond the sport.

The comeback fights that followed helped cement that transformation. In 1974 Ali traveled to Zaire to face George Foreman in the legendary The Rumble in the Jungle. Foreman was younger, stronger, and widely expected to win easily.

Instead Ali introduced the world to the “rope-a-dope,” leaning back against the ropes and absorbing Foreman’s punches until the younger champion exhausted himself. In the eighth round Ali knocked him out.

It was one of the great theatrical moments in sports history: the exiled champion returning to reclaim the crown.

But somewhere along the way Ali’s comeback had begun to operate on another level entirely.

He had become something more than a boxer. Part athlete, part moral figure, part living myth. And like all myths, the Ali story eventually began to generate episodes that feel almost too perfectly suited to the character.

One of the strangest of these occurred in Los Angeles in 1981.

A man was threatening to jump from the ledge of a ninth-floor building. Police had been negotiating for hours. Crowds gathered below, watching the terrible drama unfold at a distance.

Then Muhammad Ali arrived.

Accounts differ slightly in the details, but the basic outline is consistent. Ali spoke to the man from a nearby window, urging him not to jump. Eventually the man climbed back inside the building with Ali beside him. Photographs exist of the moment, and police officers later confirmed the story.

By all reasonable accounts, Ali helped save the man’s life.

And yet the story carries a faint aura of improbability.

Not because it didn’t happen—it clearly did—but because it feels so perfectly aligned with the Ali persona that one can’t help wondering about the role of performance in the moment.

Ali had always understood something most athletes do not: that being Muhammad Ali was itself a kind of public art.

From the beginning he blurred the line between competition and theater. The rhymes, the predictions, the playful insults directed at opponents—all of it was part of a larger performance. Ali didn’t simply fight boxers. He performed the role of the greatest boxer in the world.

By the early 1980s that role had evolved even further. Ali was no longer just the heavyweight champion. He had become a global cultural figure, a symbol of resilience after exile, a man whose public presence carried moral weight.

So when the story of the suicide rescue circulated, it seemed less like an unexpected episode and more like the natural continuation of the legend.

Of course Muhammad Ali would appear at the window.

Of course Muhammad Ali would talk the man down.

Of course the cameras would be there.

None of this means the moment was insincere. Ali may well have acted from genuine compassion. But it is also possible—one suspects just slightly—that he understood something about the scene as it unfolded: that the story would become another chapter in the larger narrative of Muhammad Ali.

If so, it was a brilliant instinct.

Because the image of the champion talking a desperate man back from the ledge captures something essential about the Ali comeback. After the long years of controversy and exile, Ali returned not merely as a boxer but as a figure people wanted to believe in.

The story may be small compared with the great fights—the Rumble in the Jungle, the Thrilla in Manila. Yet in its own strange way it may be just as revealing.

A champion reclaiming his title is impressive.

A champion stepping to a window and becoming, for a moment, exactly the hero the world expects him to be—that is something else entirely.

And Muhammad Ali, more than anyone, always understood the power of the moment.

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On Talent and Talent Spotting

This piece grew out of ordinary days at school rather than any single dramatic event. It’s about leadership as I’ve experienced it—imperfect, iterative, and learned mostly through miscalibration. The Bash & Pop line isn’t about suppression; it’s about timing. Talent is fragile. So is trust.

Epigraph

“Lick it shut before I lose my guts
Or I might rip it to tiny pieces.”
—Bash & Pop, Tiny Pieces

I.

You can tell within thirty seconds which young person is carrying voltage and which one is carrying rehearsal. At Rits Uji it happens once or twice a year: a student, or a recent graduate drifting back onto campus, unmistakably alive. It’s not polish. It’s not performance. It’s the high of being, for once, unedited. They don’t need to say much. You see it in the way they stand, in the way they occupy air without apology.

When that happens, the moment goes strangely timeless. I don’t feel older or younger—I feel outside of age entirely, the way I used to at the International Student Forum when a handful of kids ran circles around the adults simply because their energy was cleaner. That’s when I have to be careful. The instinct to spill truth rises fast, to say something too honest or too directional. I’ve gotten it wrong before—said too much, too soon, watched a young person recoil from a truth they weren’t ready to carry. That’s when the Bash & Pop line surfaces: seal it before instinct turns into damage.

II.

Youth talent isn’t just something you identify; it’s something you steward. And stewardship starts long before contracts, titles, or decisions about who someone is going to become. At Rits Uji my job is mostly invisible: CAS, Student Council, the quiet nemawashi that turns chaos into consensus. But the real work happens in smaller moments—when someone bright crosses your field of vision and you feel the spark you could either fan or overwhelm.

That’s the danger. Talent doesn’t need fireworks; it needs pacing. Recognition without collapse. Direction without hijacking momentum. My own instinct can run hot—I want to give the whole truth at once, to offer the map before they’ve even decided where they’re going. Leadership, for me, has meant learning restraint. Not caution. Respect for the shape that hasn’t formed yet.

III.

The flip side of youth talent is youth fragility. It’s just as easy to read. Today it was a judo kid—curled in the nurse center, eyes red, voice small—caught in the churn that forms when discipline starts to eclipse humanity. You can see when excellence becomes pressure, when identity narrows to a single verb.

That responsibility feels heavier. One wrong word—one too-direct truth—can land harder than anything they face on the mat. So I measured my voice. Offered steadiness instead of analysis. The temptation to diagnose, to explain the larger pattern, was there. But not every insight needs to be spoken in real time. Sometimes leadership means keeping the ink from running red.

IV.

Restraint has a cost. Not dramatic. Just a quiet pressure in the chest—the sense of holding back a sentence that arrives fully formed but can’t yet be given. That’s the part of leadership no training covers: seeing a young person clearly and deciding how much of that clarity they can carry.

You swallow the rest. Not because you doubt it, but because timing matters more than brilliance. The wrong truth, delivered too early, can fracture trust. The right truth, delivered at the right moment, steadies the ground under someone who is still learning how to stand.

V.

With my son, talent has never been about molding or steering. It’s the opposite. I want his spark to move in whatever direction it’s already leaning, and I want to run alongside for as long as he’ll let me. That’s the calibration I carry into school without meaning to—the belief that momentum matters more than mastery, that the job isn’t to sculpt but to notice and match pace without crowding.

Watching him grow taught me the discipline I try to practice at Rits Uji: let the young be young. Let the talent be wide before it is refined. When the moment grows too bright or too raw, when the truth wants to spill too quickly, the choice isn’t silence. It’s timing.

VI.

In the end, talent spotting is less about brilliance than about restraint. Not leading from the front, not pushing from behind, but matching rhythm long enough for someone to find their stride. Youth talent dazzles. Youth fragility aches. Somewhere in that overlap, leadership becomes atmospheric rather than performative.

They don’t need speeches or interventions or the full weight of truths learned the hard way. They need someone who can read the moment, steady the air, and resist tearing it open before its time. And if you’ve judged the moment correctly, they outrun you.

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On the Top Five Male Athletes of All Time

Note: Today I am releasing the first of four pieces in a long-gestating project on the greatest athletes of all time. Like all lists, I am fully aware that this will engender disagreement, and that’s part of the point. My criteria include sporting accomplishments — championships, MVPs, world records — as well as off-the-field impact and historical significance. Some figures, like Michael Jordan, have a mixed legacy; others, like Pelé, have an almost unblemished one. I would love to hear your thoughts, so please do consider dropping a comment whether you agree or disagree. This piece will be followed by numbers six through ten for the men, and then a separate top ten for women.

1. Babe Ruth

Babe Ruth remains the number one choice. He completely changed the game of baseball with his power hitting and his two-way play. America’s game would never be the same. From humble beginnings in Baltimore, he became the highest-paid and most visible athlete in the world. His larger-than-life personality — the booze, the women, the cigars — all contribute to his myth.

The 1927 Yankees remain shorthand for the greatest team ever assembled, and Ruth’s pairing with Lou Gehrig gave baseball one of its most iconic duos. The relatively early deaths of both men add a certain pathos to the story. Ruth won seven World Series titles, hit 714 home runs in an era when power was rare, and essentially invented the modern slugger. He even has an iconic candy bar named after him. Unassailable.

2. Muhammad Ali

Next to Ruth, Ali is 1A. You could argue Jordan for pure dominance and brand success, but Ali was not only great in the ring — he intersects with 20th-century history in ways that put him over the top.

From his origins as Olympic gold medalist Cassius Clay to his name change, his foregrounding of Muslim identity, his refusal to fight in the Vietnam War, and his connections to the Black Power movement and Malcolm X, Ali became far more than a boxer. He later paid a tragic physical price for fighting too long, and his public battle with Parkinson’s disease only deepened his stature.

Ali talked better than anyone before or since, floated like a butterfly, stung like a bee, and was a three-time heavyweight champion of the world. He looms large not just in sport, but in global cultural memory. A clear number two.

3. Michael Jordan

Jordan comes in at number three — though among younger generations he is arguably better remembered than Ruth or Ali, which suggests that his status may continue to rise.

From his famous early cut from his high school varsity team, to the game-winning shot as a freshman at North Carolina in 1982, to his early playoff frustrations against Boston and Detroit, Jordan’s arc is mythically clean. Once he broke through, the dominance was total: six NBA championships, five MVPs, ten scoring titles, and an undefeated Finals record.

Off the court, Jordan became the most successful sports marketer in history. His shoe deals and advertising footprint dwarfed anything that came before. His legacy is not without complications — gambling rumors, the David Stern suspension theories, a rocky tenure as owner of the Charlotte Hornets, and an ongoing public feud with Scottie Pippen — but none of that erases what he was on the court. An undeniable number three.

4. Pelé

Pelé belongs at number four because he remains the single greatest icon in what is almost certainly the world’s most popular sport. I grew up on basketball, baseball, and football, yet even I knew who Pelé was by the age of six.

For people like my son — a soccer fan and influencer — Pelé is bigger than Ruth or Ali. Other players, Messi included, may rival or surpass him on pure technical grounds, and Maradona has a competing mythos, but Pelé’s status as a hero from the global south remains unmatched.

He won three World Cups with Brazil, scored over 1,000 career goals depending on how one counts, and became the first truly global sports celebrity. By all accounts, he was also a gracious and generous human being. There is little that detracts from his legacy. A natural number four.

5. Jackie Robinson

Jackie Robinson belongs on this list for his brave and immensely graceful breaking of baseball’s color barrier — and by extension, professional team sports in America.

Credit is due to Branch Rickey for taking the risk, but it was Robinson who carried the weight. Through his base stealing, his hitting, his defense, and above all his composure, Robinson became a model of quiet strength and dignity under pressure. He won the inaugural Rookie of the Year award, an MVP, a World Series title, and was a perennial All-Star.

One may admire Jordan without loving him, but Robinson is universally — and rightly — beloved. He helped reshape not just baseball, but American race relations more broadly. A fitting number five.

Dedication:

For Steve Treader, the greatest sportswriter I know.