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.” 

There’ve been a lot of things written that aren’t necessarily correct about me. So we were nervous. We got double-crossed by the people in The Last Dance. They sent a whole crew to Palm Springs and I talked [on camera] for three and a half hours. I was dubious because I hadn’t talked to anybody at Nike for years. Well, the end result was, in The Last Dance, all you could see was my rear end. They never used anything that I said.

I knew that Matt and Ben were gonna be involved but they weren’t officially involved—they were still signing the contracts. But Mandalay Bay and Sky Dance, this was major. I saw the other people involved—they told me about the actors, “You’re going to have the crème de la crème.” We agreed to do the movie.

So how did you consult on the film?

Alex comes up to Palm Springs, we get lunch, and he starts telling me about his idea. We we there for a minimum of three hours. He asked all the intimate questions of my life. Then I get a call saying, Matt Damon wants to speak to you. So we made arrangements to do a 90-minute Zoom. The first thing he said, to make it easy for me, was, “Sonny, I just wanted you to know, I’m a big basketball fan. I grew up five and a half blocks from Patrick Ewing. I went to Ridge Latin High School.” That’s where Patrick went to high school in Massachusetts. I’m a major Celtics fan. So he cracked the ice telling me that. Beautiful. We talked for an hour and a half that day. We talked about Rounders—I love poker. In fact, I wish they’d used a poker scene in Air rather than dice.

When they told me they were going to use dice, I said, “What’s wrong?” He said, “Sonny, it takes five hours to shoot a poker scene. One card comes, you flip a card…we ain’t got that much time. But dice. You get the damn dice, you roll it out in about 30 seconds, the game’s over.”

How did it feel to have Matt Damon play you?

You know, I’ve watched everything he’s done—Mr. Ripley, Good Will Hunting, Jason Bourne. I mean, he and Ben wrote Good Will Hunting. These two guys are winning Oscars and they look, especially Matt, like he’s 15 years old. But Julie, how in the hell can a kid from Trafford who graduated third from the bottom of his class end up in a movie with Matt Damon playing him? I can only tell you it’s an impossible dream.

What was your actual relationship with Michael’s mother, Deloris, like? In the movie, we see your character go down to North Carolina to introduce yourself.

Every conversation I had with Mrs. Jordan was on the phone. I had not met her until that day of the big meeting. The story behind that is, as I left Tony Roma’s with Michael [after our first meeting], and I thought it was over—he called Nike “Nicky,” and said Adidas had the best clothes—I asked Michael, “Who’s your best friend?” Because I knew I wasn’t going to get him after that first meeting. He was doing a favor for George Raveling, the assistant coach on the Olympic team and my best man at my wedding, meeting me. I gotta try one more time to get ahold of somebody else to talk him into this. I thought when I asked, he would tell me one of the players or Coach Dean Smith.

His answer to me, as he’s walking out of Tony Roma’s, was, “my family. They’re my best friend.” And he kept walking.

I ask somebody. I get [Deloris’s] number. I make a phone call and we start conversing. And that’s what led to that last meeting [in Oregon]. Mrs. Jordan and I formed a relationship, talking on the phone, and she and I became very close through life. The closest to honest thing about the whole movie is my relationship with Mrs. Jordan…that was real.

And you know, I hadn’t met Viola until the [premiere] party. Pam and I went over and introduced ourselves. She knew who I was right away. And she thanked me and she hugged me. As we’re hugging, as God is my judge, she says, “Son, I want to tell you something. I talked to Deloris Jordan yesterday. She told me to say hello to Pam and Sonny.” Pam and I cried.

What about the climactic scene where Matt Damon, as you, is in the big meeting with Michael Jordan and his family, pitching them on why they should sign with Nike. And Matt’s Sonny gives this incredible, showstopping speech—predicting what will happen in his life and career. Was there any truth to those words? Do you remember what you said in the meeting?

I didn’t make the whole speech—they created some of that. But I did have my minute in the sun. I did take over—we were showing film and the shoes and all that stuff. And [Michael and his family] were bored. They’re like, what are we waiting for? And I’m sensing this.

I knew that I had to do something to pep up this conversation. And I did speak. Whether I gave this, you know, last will and testament of mankind [laughs]…Matt did a hell of a lot better than I did. But that scene happened. Maybe not the exact words. One of the most seminal things is when Peter [Moore] showed her the shoe, she did say something very similar to, “It’s just a shoe until my son puts his foot in it.” That’s how she was. “Do we own a piece of this or do we not own the piece?” Obviously everybody [in the room] was involved, but I had my moment in the sun.

After that meeting, I got involved with the family. We traveled to Europe together. They had disagreements during the time with Nike where I was the intermediary. We sold Michael’s sister a treadmill ’cause I couldn’t get on the damn treadmill.

Michael gave Ben Affleck his blessing to make the movie. Have you heard from Michael?

I still haven’t talked to Michael. I haven’t talked to anybody from Nike. I had a couple ex-employees call me. But I can tell you this. Ben went to Michael, spent a day on the golf course with him, and Michael gave him his blessing. When Ben asked him, “Do you have any problems with Sonny?” He said, “I have no problem with Sonny.”

When I started to work for Adidas, we were now on opposite sides of the fence. Nike was my biggest competition…my parting with Nike and Michael, that was business.

You first met Michael before he knew how to pronounce Nike, and had a front-row seat to him becoming a world superstar—in large part because of Nike’s branding of him. How does fame change a person?

What I found out in the 10 years with Michael, especially the tour, ’cause it was more intimate then, was Michael has two lives. He has two personalities. He is this great athlete that does extraordinary things athletically, but he has this mindset that he can divorce himself from people and be a private person. He had different relationships with different people and very few intimate. Michael had problems with his teammates, didn’t get along with everybody. Didn’t mean guys on the team hated them. He just didn’t get along with him. He’s also the same guy who said, “Republicans buy sneakers too.” Michael in my mind is two different people that achieved the same goal because the same goal was to be a great basketball player. He had the aptitude and the mindset to want more in signing a contract—and his mother guided him into that. He took that mindset to own part of Nike and create it as a business.

LeBron, Kobe, all these guys got a piece of whatever. Maybe Victor [Wembanya’s] going to get a piece. This new kid. If I’m Victor’s agent, I want a piece of it right now. Not five years from now to see if he makes the All-Star team. He’s in a place now to own a piece of somebody. And if I’m a new company, I sign him. ’Cause he’s supposed to be damn good.

But no one else came out and did for shoes what Michael did. He created a new industry for the athlete. Not only were they getting paid more, they had a chance to put their name on the product. No one can ever do that again.

Air depicts this glorious high in your relationship with Michael with Nike. But after this deal, you were pushed out of Nike, you say the FBI investigated you for corporate espionage, your role in the Nike deal was later minimized by Phil Knight. There was The Last Dance controversy. Did these feel like heartbreaks or was it just business?

I was never a businessman, Julie. I was a kid with a lot of good ideas. It hurt. I was disappointed a lot but it never destroyed me. I didn’t always get a chance to answer an accusation. A more powerful individual or group always gets the last word in the media, right? I was never really afforded that opportunity to say, well, that didn’t happen that way. I wasn’t in place to call press conference in my life, right?

Sometimes it’s business for the other person. For me, it’s always been personal. My relationships are all personal. When Adidas lied to me, I quit. They told me they’d give me $100 million [to sign LeBron James]. They gave me $70 million. They put it [the rest] in incentives. I quit. Why? Because I told [LeBron’s mother] Gloria in person, LeBron in a hotel room when he was a senior in high school, you’re going to get $100 million. We get there to sign the damn contract. I opened it up and it was, you know, it wasn’t a hundred million, another 30 million total in incentives. Incentives meant nothing to me. My idea is, give all the money now. If you’re scared [and offering] incentives, don’t give the damn deal.

I grew up gambling in Trafford. Playing poker was a ritual birth. We all did it. We all played in the number games. I went to Las Vegas when I graduated from college. I won. I lost. I was good. I was bad. But I was always Sonny.

The resulting conversation has been edited and condensed for clarity.