In a Hollywood Reporter essay, former uber NBA agent Arn Tellem -- who is now vice chairman of the Pistons and who is married to former longtime CBS boss Nancy Tellem -- describes the HBO Showtime Lakers drama as "cruel, dishonest and staggeringly insensitive," especially in its treatment of Jerry West. "The show’s paradox is that it prides itself on being faithful to the facts, and yet — between the formulaic script and stick-figure cartoon characters — reality seldom intrudes," says Tellem. "Hiding behind the disclaimer 'this series is a dramatization,' Winning Time imagines itself a 'satire' that treats pretty much everyone with equal odium, covers pretty much everything with equal ordure. Pro basketball players are greedy braggarts and narcissists; pro basketball owners, ruthless bigots and hedonists. Of all the athletes and executives shamed and ridiculed in the first two episodes, the most brutal — and gratuitous — character assassination was reserved for Jerry West (played in the series by Jason Clarke), the universally beloved former Lakers player, coach and general manager known as Mr. Clutch. In the series opener, which aired on March 6, his character seemed to be modeled on Yosemite Sam — a boozy, impulsive hothead who steamrollered anyone in his path, angrily snapped a golf club over his knee and stormed away to curse out a colleague, and chucked his 1969 NBA Finals MVP trophy through his office window in a fit of frustration. Never mind that West is a health nut who has always shied away from alcohol. Never mind he’s not just a gentleman but a gentle man who prides himself on treating others with grace and compassion. And never mind that his old office at the 'Fabulous Forum' didn’t have windows. Indeed, none of the arena’s basketball offices did. I ought to know. I was there."
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Sally Field was ready to sign on to Winning Time without reading the script: “I saw the pilot that Adam McKay did and it was really, really good," says Field, who plays the mother of John C. Reilly's Jerry Buss. But beyond being an avid Lakers fan, Field was attracted to the story Winning Time is telling. "It's about culture in LA in the late '70s, both the Black culture, the business culture, and the pressure of these young talents that are taken out of their families and thrust into a big arena," she says. "It also takes a look at the whole machinery behind what this is.”
Michael Chiklis is okay with portraying his beloved Red Auerbach as an antagonist: "I knew I was being cast in the role of one of the principal antagonists, and that’s fine," he says. "I’m sure Red would have loved that. If you’re going to tell a story from the Laker standpoint, no one’s gonna be hated more than Red Auerbach and Larry Bird and the boys from that Celtics team. Everything I’ve researched and looked into says that Red Auerbach was universally loved and respected and admired by his players, the administrations he worked with, and the fans in the Boston area. Conversely, if you played against Red Auerbach, you f*cking hated him. He was a gamesman, so he was there to beat you and would do everything he could to make that happen."
Quincy Isaiah recalls landing Winning Time's Magic Johnson role after a "slow burn" of an acting career: "Yeah, I screamed," he says with a laugh, recalling a call from executive producer Adam McKay and casting director Francine Maisler. "I had to put the phone on mute. I just screamed and ran around in circles. Took it off mute, told them 'thank you, I look forward to working with y'all', hung up the phone, did it again, and then called my mum and then she did it too."
Nailing his dad Norm Nixon's mannerisms, voice and cadence was easy for DeVaughn Nixon: But DeVaughn says the physical aspect of it was a challenge. “I had to drop 30 pounds and had to get shredded,” he says. “I had to really fine tune my basketball skills as well and become a baller again, because I hadn’t touched the ball since high school.”