Ben Affleck didn’t set out to make a film about Gerry Cardinale, but the founder and managing partner of RedBird Capital Partners is nonetheless present in every frame of the upcoming Air. His is not a physical manifestation—you won’t spot the investor in a cameo opposite Affleck’s extravagantly begoggled Nike boss Phil Knight or Matt Damon’s carbohydrate-enhanced embodiment of Beaverton brand-whisperer Sonny Vaccaro—but the finished product serves as a recapitulation of Cardinale’s entire career as a dealmaker.
“This movie is the ultimate expression of the three rings of my Venn diagram, and the way I invest, which are: sports, media and culture,” Cardinale said this week during a teleconference with Sportico. “I mean, you talk about convergence.”
In the midst of one of his innumerable trans-Atlantic business trips, Cardinale’s on his way to Lombardy, where he’ll meet with a delegation of local power brokers to discuss plans to construct a new stadium for the Serie A club AC Milan. The legacy venue, San Siro, was built 97 years ago and is perhaps best described as “decrepito.”
The first title to premiere under Affleck and Damon’s RedBird-backed Artists Equity banner, Air was co-produced by Amazon Studios and Skydance Sports, the recently launched Skydance Media offshoot that also happens to be in cahoots with the NFL. RedBird also has a partnership in place with Skydance, which means that Cardinale has two lines plugged into the film. While it may be more expedient to rattle off a list of companies in which RedBird hasn’t invested, Cardinale’s many other high-gloss ventures include AC Milan, Fenway Sports Group, the XFL and YES Network.
While the film serves as the story of Vaccaro’s obsessive pursuit of Chicago Bulls rookie Michael Jordan, around whom the shoe salesman hopes to launch a line of basketball sneakers, Air is less a sports movie than it is a chronicle of a myth in the making. It’s about the transformative powers of raw belief, and the magic that happens when greatness intersects with obsession.
Cardinale refers to Air as “Moneyball on steroids,” although that may be understating the appeal of the project, which is heightened by Affleck’s deft handling of the material and the heady dopamine fix of early-‘80s nostalgia. (If the prospect of a Good Will Hunting reunion isn’t sufficient to get fannies in the seats, the sensory overload of watching Batman in Blue Blockers and a harried Damon rocking a goofy wig is worth the price of admission alone. Nothing says “Boston” quite like forcing your best friend to undergo a dumpy makeover right before you start yelling at him through a bullhorn every day for two months.)
While Air encapsulates so much of what is essential to Cardinale’s business philosophy, it also serves as a reminder of just how much the world has changed since Vaccaro was out courting Jordan. “It’s really about the legacy of Phil and what Nike has done, and yet it’s also coming out just as Michael is deliberating on the sale of the Hornets,” Cardinale said. “So, on the one hand, you have this examination of the impact of this seminal moment in sports and culture, and at the same time, there’s this invisible, god-like figure at the center of it all, and today he’s arguably the biggest intellectual property in all of sports. There’s a lot coming together here.”
(As Affleck has explained it, Jordan remains unseen throughout the film because the role is impossible to cast. The minute you show an actor who’s meant to be the living manifestation of a young Michael Jordan, everyone in the theater immediately nopes out. Nobody is Michael Jordan, and that’s exactly who you see up there on the screen.)
If Air is a feel-good movie about underdogs—and a wholly unseen Top Dog—Cardinale believes that many in today’s megabillion-dollar sports-industrial complex may be in for a less-than-happy ending. “With sports, there’s been a bubble, and these asset valuations have exploded, but none of the infrastructure has kept pace,” he said. “So they’re looking for new ways to narrow that gap. I usually go into that gap, and I close it by building these companies. Because one leg of the stool isn’t enough to keep you from toppling over.
“Sports today is a media story. It’s a culture story,” Cardinal added. “From where I sit, sports as a standalone entity has maxed itself out; it’s like Adam Smith and the tulip craze. You know, when you start hearing about people very freely talking about sports as an asset class, that’s when you gotta stop and be like, ‘uh oh.’ You see all this capital being raised to take minority stakes in teams that control premium valuations with no governance, and that’s just because investors want to be able to check the box and say they have sports exposure. And it’s just anti-Darwinian. It’s not sustainable, and it’s not responsible. And so yeah, I think we’re in a bubble.”
Cardinale is still a true believer in sports as a value proposition, and he’ll continue to invest during the shifting economic cycles. Case in point: One of RedBird’s biggest investments, with Fenway Sports Group, came together in May 2021, in the midst of a global pandemic. But risk management plays a big part in managing a $7.5 billion firm, and so the RedBird playbook never strays far from the fundamentals of his Venn diagram thesis.
The diversity of RedBird’s portfolio is a reflection of many of the lessons Cardinale learned from George Steinbrenner nearly 25 years ago when they worked together on a big-swing media play that would become YES Network. Instead of piecemeal rights fees, the forward-looking (and, it probably goes without saying, deep-pocketed) owner gins up a delivery system for equity.
“You gotta hand it to George, right? He was a visionary,” Cardinale said. “And that, basically, is my whole career. Everything I’ve done is really some version of that.”
