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‘Air’: The Real Sonny Vaccaro on Matt Damon, Michael Jordan, and Shoe-Biz Heartbreak

To some people, the sneaker industry might not seem very sexy—but Sonny Vaccaro, the man who introduced Michael Jordan to Nike and helped broker the landmark deal in 1984, has blazed an operatic arc in his career, filled with hundreds of millions of dollars in deals, world superstars, and gut-wrenching betrayals.

By befriending Jordan’s mother, Deloris, in the early 1980s, the Trafford, Pennsylvania, native ended up signing Jordan to the athlete’s first shoe contract before Jordan had played a single game for the Chicago Bulls. The deal, which gave Jordan a piece of Air Jordan profits, catapulted Nike to the front of the shoe industry and revolutionized sports marketing. (According to one estimate, Jordan made over $1 billion from Nike by 2020.) In the decades since, Vaccaro was fired from Nike, allegedly investigated by the FBI as part of an investigation into corporate espionage, hired by Adidas (where he signed Kobe Bryant as a high school student), and then, according to Vaccaro, burned by Adidas over what he says was supposed to be a $100 million deal with LeBron James. (Adidas ended up offering James less money, lining his deal with incentives instead; James signed with Nike.) Vaccaro resigned shortly after.

Vaccaro hasn’t just advocated for athletes in the shoe industry, though—he cofounded the Dapper Dan Roundball Classic, a showcase for high school players, in the 1960s; launched the ABCD basketball camp, to help promote the country’s best players, in the 1980s; and scored a major win for college athletes in 2014 after leading a major case against the NCAA that resulted in college athletes being paid for the use of their names and images in video games and television broadcasts.

In recent years, though, Vaccaro claims that Nike has tried to minimize his role in the Jordan deal and Jordan’s growth into a global phenomenon—an allegedly revisionist history that, for Vaccaro, boiled over when he was cut entirely from ESPN’s 10-part documentary The Last Dance. (To prove his significance in Jordan’s ascendancy, Vaccaro auctioned off a pair of autographed black Air Jordan VIs that Jordan gave him after wearing them to start Game 4 of the 1991 NBA Finals.) This recent controversy is partly why Ben Affleck’s new movie, Air, is especially sweet for Vaccaro. Not only is Vaccaro played by Matt Damon, but he’s the hero of the film—putting him in the center of negotiations, as he develops a relationship with Deloris Jordan (Viola Davis) and ultimately gives a showstopping speech convincing the Jordans to sign with Nike. 

Though Vaccaro says he did not get to see the Air script, even as a consultant on the film, it was informed by his words. About eight years ago, Vaccaro was the subject of a 30 for 30 episode called “Sole Man.” An intern on that show, Alex Convery, had access to Vaccaro’s transcripts and ended up writing the film, which was included on 2021’s Black List roundup of the best unproduced screenplays.

On Wednesday, the same day Air was released in theaters, Vaccaro, an energetic 83-year-old, called VF from the Palm Springs home he shares with his wife, Pam. In a long conversation, Vaccaro talked about his first conversation with Matt Damon, his memory of the landmark Jordan deal, the teenage player he’d want to sign now if he was still in the shoe industry, and much more.

Vanity Fair: When did you first hear that a movie about you was in the works?

Sonny Vaccaro: When the Rams played in the Super Bowl two years ago, [Skydance Sports president] Jon Weinbach calls me and says he and [Mandalay Entertainment founder and CEO] Peter Guber have a project they’re doing that they want me involved with and it includes Michael Jordan. That’s all they told me. Pam and I go down to Beverly Hills and for three and a half hours we have lunch with him and about 15 people. He invites me to be a part of it—as a consultant. But said, “We’re not going to share the script. You have no control over it or editing.”