When Sean Patrick Small was a teenager, people were always telling him that he reminded them of Larry Bird. Some of this was his own doing—he wore no. 33 on his high school basketball team in Los Altos, California, after all—but much of it was just the way he looked. Six-foot-4; hair the color of wet sand; a stoic resting face. Later, as a film student at the University of Southern California, Small found himself mulling over Bird’s past as he considered his own future.
“I was trying to think about how to, you know, make this acting and writing career kind of move forward together,” Small tells me over Zoom in the middle of July. (Our interview, like all the others for this story, took place prior to the SAG-AFTRA strike.) “And so I was like, I’m going to write a role that I could play.”
In 2014, Small started working on a miniseries about Bird, based in part on a book he’d read and optioned called When March Went Mad. Small researched and wrote and pitched the show for years. The director of Coach Carter signed on. Small kept shopping his idea around, and in doing so, he caught wind of a project that had already been green-lit and had also spent years in development: a program about the rise and fall and rise and rise of the 1980s Los Angeles Lakers, based on the Jeff Pearlman book Showtime. “I heard about Winning Time,” says Small, “and I was like, I’m definitely going to watch that show! Maybe they’ll have a Larry Bird character within it!”
Sure enough, there was a Larry Bird character—set to be played by Bo Burnham. But Burnham dropped out in 2021, citing scheduling issues. Soon after, Small’s sister-in-law’s friend happened to spot a new casting notice for the part of Bird. Small submitted a self-tape for the role, was invited to do another audition over Zoom, and then got called back to another virtual session in front of producers. “I was on set two weeks later,” he says.
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“I mean, it was just like—this six to seven years of work and research that culminated into these two to four weeks of auditioning and getting the role and being on set,” Small says. “As Larry Bird would say: ‘Luck favors the prepared.’ So I was prepared for the moment, I jumped at it, and now we’re here.”
Luck, favor, and preparation happen to be three of the themes underpinning Winning Time, which begins its second season this Sunday on HBO. That goes not only for the characters in the story—and for the real-life people and events that inspired them—but also for many of the Winning Time actors themselves.
Some of them, like Small, or Quincy Isaiah and Solomon Hughes, who play teammates Magic Johnson and Kareem Abdul-Jabbar, respectively, joined this cast as near-rookies getting their big breaks. Others, like Michael Chiklis, cast as Boston Celtics pooh-bah Red Auerbach, are veteran talents who wound up on Winning Time thanks to some small bit of serendipity. John C. Reilly may be the straw that stirs the drink with his bombastic, gleeful performance as Lakers team owner Jerry Buss, but even he is a guy who came in off the bench, so to speak, to earn a starting role in this production. All these winding paths inform and enhance Winning Time in Season 2, as its characters deal with new champagne problems, old lingering hang-ups, and constantly having to audition for your own job. At its best, Winning Time is a show about creativity, basketball, persistence—and about how sometimes you wait your whole life for everything to change in an instant.
The simplest kind of sports lore is when the winning comes at the end. Like when a plucky, ragtag group raises an improbable trophy. Or when a determined athlete (or two) overcomes personal setbacks to take home the gold. Or like last spring’s Winning Time debut, which kicked off with a charming hustler in Jerry Buss (Reilly) buying a basketball team and concluded with said basketball team winning the 1979-80 NBA title. The show’s first season had an arc as satisfying as a skyhook swish.
“Season 1 was this story gift because it was just this Cinderella season,” says showrunner Max Borenstein. “They draft Magic. Buss buys the team. They have all these challenges—and then they win the first year, which is great.” But now, Winning Time is eager to demonstrate that success can be even more interesting when it’s only the start. The title of the Season 2 premiere, after all, is “One Ring Don’t Make a Dynasty.”
That is the first of seven episodes that explore what happens when the victors squabble over the spoils. Attention, money, and power: all of them scarce resources that are both hard-won and harder still to maintain.
Teammates like Magic and Kareem battle injuries and bristle over salaries. The Lakers coaching staff (led by Jason Segel as Paul Westhead and Adrien Brody as Pat Riley, resplendent in a stress-induced neck brace) is beset by stubbornness and the distinct paranoia of realizing that there’s a meeting happening without you. Even the Buss family feels more fractured than before, with Jerry’s three children jockeying to be validated or even just noticed by their old man. (“You’ll never be Daddy’s favorite son,” one sibling taunts another in a scene that feels like it came from Succession.) As Jeanie Buss grows more confident, “the awareness that you do know what you’re talking about comes with this sort of indignation,” says Hadley Robinson, the actress who plays the young scionne. And that’s all just the enemy within. The real big bad still looms in the Boston Celtics, led by Bird.
“We’re trying to tell the story of a dynasty,” Borenstein says, “and one season, one win doesn’t do it. So when we looked at what comes next in the story, it became clear to us that this had to be The Empire Strikes Back. This is where you’re going to face your enemy for the first time: your rival, your greatest rival. And you’re going to face every internal obstacle along the way.”
Winning Time executive producer and writer Rodney Barnes agrees. “I think facing yourself, in order to become great enough to face your greatest obstacle, makes for great television.”
How’s this for a rivalry: “Bishop Montgomery; Harvard-Westlake,” trumpets Solomon Hughes over Zoom, reminiscing about a ’90s high school boys basketball state tournament matchup that happened to pit him against his Winning Time colleague Jason Segel. “It was at Harvard-Westlake,” Hughes says.
“Their students section was crazy. They were like, organized. And I feel like they knew every personal detail about us as players, and they riled us up—” he says. Segel, who is on the same Zoom listening to all this, pipes up. “I don’t remember much,” he smirks, “because we just had our heads down, playing our way to the state title.” (Segel was part of back-to-back state champion teams in 1996 and 1997; he even earned the moniker “Doctor Dunk.”)
Segel’s antagonism is in jest, and it disappears altogether when he talks about what it’s like to work on Winning Time with someone like Hughes. A former Cal basketball captain and Harlem Globetrotter, Hughes has a PhD that involved studying recruited collegiate athletes—and a total blank slate of an IMDb page. (Hughes, 43, told Sports Illustrated that he thinks he’d been on one audition, for an Advil ad, before being recruited for Winning Time.) Watching Hughes go from being a total newbie learning the basics of blocking and camera angles to a real actor going to emotional places was like seeing “the next ascension,” as Segel puts it. “He surprised me,” he says. “And it was like, the coolest thing to watch Solomon like, just become sort of so f’ing great.”
In Winning Time, Segel’s character, the embattled Lakers head coach (and Shakespeare enthusiast) Paul Westhead, is a stickler for “the System,” his preferred style of play. When it comes to acting, Segel has a method, too. “I taught Solomon my system,” he says, blurring the line between actor playing coach and coach helping actor.
Adrien Brody takes on a similar air when talking about working with less experienced actors. His take on Pat Riley’s transformation from mustachioed has-been to slick Showtime operator is one of the most fun parts of this season—and a great example of how luck favors the prepared on this show. Paired in a Zoom room with Quincy Isaiah, the 27-year-old who plays Magic Johnson with such magnetism that he worried about his lips cracking from all the smiling, Brody says that he “took real pleasure in seeing Quincy excel in this position.”
“You know, there are a lot of parallels, I feel, to my character in this,” Brody says. “In being in a position to impart some of the wisdom that I have earned in my lifetime.” Like Hughes, Isaiah joined Winning Time with very little acting experience under his belt; before getting cast, he had grown frustrated enough with fruitless auditions that he was thinking of joining the military. Instead, Brody says, “I saw him do his thing, and he didn’t need my help.”
At that, Isaiah perks up and flashes that face-stretching smile. “You said I didn’t need your help,” he tells Brody, “but I would argue that is helpful for me—the acknowledgment.”
“That’s the truth!” Brody says. “It’s just a reminder that you’re doing it already, you know?”
“It’s nice to be verified, you know?” Isaiah says. Sometimes your own reality is easier to accept when it’s being reflected back at you. But unlike Isaiah in this particular moment, not everyone related to Winning Time is going to love what they see this season.
“YEP, THIS ACTUALLY HAPPENED,” reads an on-screen caption during a chaotic Season 2 scene involving Buss, Riley, and the hilariously volatile Jerry West—played by Jason Clarke. It’s funny, in other words, because it’s true.
On the one hand, this kind of bold assurance feels like a bit much, or at least much like a bit: a little distracting, a little too conspicuous. On the other hand, I can’t deny that when the words appear, it’s at a moment when I really could hear myself wondering: Wait, DID this really happen?!
Last season, Winning Time was not exactly merrily received by the people about whom it was written. The real-life West released a statement through his attorneys that “the Jerry West in Winning Time bears no resemblance to the real man.” Kareem panned the program on his Substack. (“If you gathered the biggest gossip-mongers from the Real Housewives franchise and they collected all the rumors they heard about each other from Twitter and then played Telephone with each other you’d have the stitched together Frankenstein’s monster that is this show,” he wrote.) Magic Johnson said that “you can’t do a story about the Lakers without the Lakers.” (The show does have some connections to the real thing, if you squint: the character of Norm Nixon is played by DeVaughn Nixon, Norm’s son.)
It was understandable that some of the principal characters in the story might react this way—after all, they are depicted doing things like smashing up pool houses, throwing trophies through glass windows, and cheating on their partners. (Also, it’s worth noting that many of them were involved in a 10-part Hulu documentary about the Lakers called Legacy that came out last fall.) But Reilly scoffed Johnson’s comments off last year. “People have said, ‘How can you tell the story of the Lakers without the Lakers themselves?’” he told Vulture. “And my answer to that is, ‘How could you tell it with them?’”
As if to preemptively shield Season 2 from criticism that its many absurdities are too embellished, the show’s creative team has started sharing episode companion PDFs that provide receipts on the amazing-but-true details. (“DID BOSTON FANS REALLY ROCK THE BUS?” is one example from the Episode 1 companion, while another guide answers the question: “DID KAREEM ACTUALLY ROLLER-BOOGIE?”) The files also admit when something has been tweaked for creative reasons, as with a composite character this season named Honey. “I think the companion guides, to be perfectly honest, were a result of some of the reactions of Season 1,” says Kevin Messick, one of the show’s executive producers. “Some of that information wasn’t out and available as readily, so therefore things become debatable to whoever Googled it last. … Hopefully it makes a little more sense or at the very least sparks a more kind of honest conversation about the show, which I think got a little bit lost last year.”
According to director and executive producer Salli Richardson-Whitfield, “we were very diligent about” getting the details right. She and her team pored over footage of, say, the 1984 NBA Finals between the Lakers and the Celtics, trying to nail every inch of screen space. “We have wardrobe there, and I’m like: Pause that tape right there. I need that guy in the blue shirt with the curly hair. I want him in that spot. OK, you see that sign? I want that sign. Because we want to recreate it as much as we can.”
But for Richardson-Whitfield and the actors she works with, some of the most important moments are still the ones they have to conjure up themselves.
“My favorite parts about working with Salli,” Isaiah says, “was the more intimate scenes and the scenes where I’m dealing with my family, or dealing with [Magic’s girlfriend] Cookie, and where [Richardson-Whitfield] is pushing me and really making me go there, and saying like, Hey, I don’t believe you, and making me fight and fight and fight and really helping me become a better actor.” The goal is to not need to remind people that THIS REALLY HAPPENED all the time.
Last year, showrunner Borenstein compared Winning Time to The Crown, the ripped-from-the-headlines show about the British royal family. And just like that show, it’s almost as fun to read up on the real stories as it is to watch the exaggerated ones on screen. But what really distinguishes Winning Time is the way there’s a third dimension to relish, too: the trajectory of the actors, rookies and journeymen alike.
Small, for instance, made some appearances in Winning Time’s debut last spring, but he really shines in Season 2. He hoops in jeans; he stares tragedy in the face; he carries himself with an air of blank disdain. And he resembles Bird even with the ball in his hands. “I’ve watched you,” says Chiklis, who plays Red Auerbach, to Small with admiration during our interview. “I’m like, holy shit, you got Larry’s shot!”
That part took some doing: Small worked intensively with NBA shooting guru Idan Ravin to emulate Bird’s mechanics and silhouette, breaking down his own basketball habits and relearning how to shoot from scratch. (“You’re paying me to train to become Larry Bird with the guy who is training NBA All-Stars?” Small says incredulously. “I mean, I’m living the good life right now!”)
Chiklis notes that his own casting was, fittingly, a stroke of luck on top of a stroke of luck. First, someone dropped out of a tiny role in the movie Don’t Look Up, a project from Adam McKay, who is a Winning Time executive producer. Chiklis was cast for a one-day cameo in the film, and that day, McKay realized that Chiklis could make a great Red Auerbach. He told Chiklis to call his agent, because he had just offered him the role. “I said, don’t eff with me, man,” Chiklis says. “He goes, ‘I would never eff with you.’ And sure enough, he wasn’t.”
The role of Jerry Buss, meanwhile, was once assigned to Michael Shannon, and for a time, reportedly, Will Ferrell. But a season in, it’s hard to imagine someone other than Reilly playing the character. (Even the real Jeanie Buss admitted to Variety that she thought Reilly should win an Emmy for his work.) In Season 1, Reilly’s Buss is a showman through and through, installing glitzy dancers and playing a sort of three-card monte with the finances of the team. In the second season, as problems with the Lakers pile up publicly and Magic grows disgruntled, Buss’s disposition darkens just enough to cause a few shivers. He is by turns goofy and kinda scary, his affability cut with glinting menace. When Westhead, the team’s head coach, uses the innocuous phrase “my team” in conversation, Buss flips from gladhander-in-the-middle-of-mixing-a-drink to stone-cold-assassin-who-refuses-to-share. “Actually, it’s MY team,” he responds.
“That’s like being a leader, you know? And that’s something I had to learn how to be, actually, on this job,” Reilly says. “Sometimes it’s the tickle, and sometimes it’s the slap. I think those are both in the toolbox: intimidation and encouragement. Bonhomie and, like, threats. People have to know that you mean what you say, and then you’re going to back up your words. I learned that early on as a kid on the South Side of Chicago.”
Reilly smiles. “I say, you know what? The road behind me is strewn with people that underestimated me.” When he puts it that way, he suddenly looks just like Buss. Not everything in Winning Time is verbatim, sure. (Except the parts that are!) But sometimes, as in this second season, it’s the interpretation that speaks loudest.
