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Writing ‘Air’ Meant Untangling the “Rashomon of Shoe Deals”

In the spring of 2020, Alex Convery was feeling stuck—and not just because he was trapped in his home like the rest of us. Despite landing two of his scripts on the celebrated Black List by that point, he was struggling to find any traction in his career. Everything changed when he watched The Last Dance, the highly anticipated documentary that chronicled the historic run of Michael Jordan and his six-time-NBA-champions, the Chicago Bulls. But Convery was most intrigued by something that was barely addressed in the 10-hour series. 

“I saw that little two-minute segment on Nike and Air Jordan, and how the deal never should have happened, and all these strategic missteps by Adidas and Converse. And I had this eureka moment of, ‘Man, that would be such a cool movie,’” he says. “Everyone has their own version of the deal, but there’s only one guy who said, ‘Jordan’s the guy—go sign Jordan.’ And that’s why, to me, it was always worth taking [Sonny Vaccaro’s] point of view.”

And thus Air took flight. Written by Convery and directed by Ben Affleck, the charming sports drama stars Affleck BFF Matt Damon as Vaccaro, who puts his career and reputation on the line in the hopes of landing Jordan—a then 21-year-old who was far from a lock to be the league’s next star. The A-list cast also includes Viola Davis as Jordan’s mother, Deloris Jordan; Jason Bateman as Nike’s former director of marketing, Rob Strasser; Chris Tucker as Nike executive Howard White; Chris Messina as Jordan’s powerful agent, David Falk; and Affleck as Nike cofounder Phil Knight.

Vaccaro had made his name in high school basketball circles, starting the first national all-star game as well as an elite camp that became a showcase for future stars like Kobe Bryant and LeBron James. But his true claim to fame came in 1984, when he managed to sign Jordan. Nike originally thought the debut Air Jordan would earn $3 million over its first three years on shelves. Instead, it earned $126 million…in year one. 

Convery approached Air as a heist or caper film. “For a movie like this where you don’t have the benefit of explosions and action scenes, you have to find other ways to inject tension into it and find that conflict,” he says. He found plenty of that conflict as he pored through Vaccaro interviews on YouTube and read ESPN writer Wright Thompson’s stories about Michael Jordan; Knight’s memoir, Shoe Dog; and Swoosh: The Unauthorized Story of Nike and the Men Who Played There, cowritten by Strasser’s widow, Julie Strasser.

While Convery chose to follow Vaccaro, others have claimed to be the Jordan deal’s true MVP. “They call it the Rashomon of shoe deals for a reason,” Convery says. “In success, everyone wants to go back and take a piece of that credit. And look: Who’s right, who’s wrong, that’s not necessarily for me to say. We’re just trying to capture, maybe not the capital-T truth, but the essence of the moment.” Convery says Vaccaro told him, “‘All of these conversations happened.’ Did they happen in this order, at these locations, at this exact timing? No. But we’re making movies so there’s always going to be dramatic liberties.”

After Convery finished his script, he got in touch with Vaccaro and drove to his home in Palm Springs for a daylong visit. “We went through the script and talked about what I got right, what I got wrong, what was important to them, and the stuff that wasn’t necessarily important,” he says.

But the real game changer was Affleck coming on board as director, producer, and actor in the supporting role of Knight. Unsurprisingly, the decorated filmmaker arrived with his own ideas about what would happen in Air—and with Matt Damon. The Good Will Hunting duo took their own pass at Convery’s script, which both thrilled the young writer and worried him. Affleck’s next request was also a tall order: “From day one, he said, ‘I want Michael’s blessing. I won’t do it unless he’s okay with it,’” Convery says.

Thankfully, Affleck got Jordan on board—though not in the film. While Damian Delano Young acts as a stand-in for the athlete, Jordan isn’t a character in Air; his face is shown only in archival photos and footage, and Delano Young has only two lines (“hello” and “Bulls colors”). Why? “The minute you cast someone as Michael Jordan, that’s going to be the headline around the movie, and sets a whole different expectation,” Convery explains.