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The Business Behind the Characters of ‘AIR’

Last Updated: December 22, 2023
Boardroom got insight from former Nike alum and the Ben Affleck film’s star-studded cast to learn all about who made Nike’s Michael Jordan deal happen.

The Air Jordan empire is one that churns out over $5 billion in annual revenue.

Thirty-seven years ago, the namesake sneakers tied to Mike held another position inside the offices of Beaverton and at shoe stores across the country.

“The Air Jordan was the only basketball shoe we could sell,” Ron Hill, a former Nike employee who oversaw product merchandising in the ’80s and ’90s, told Boardroom in 2022.

Michael Jordan poster (Image via Nike)

As it stands, the Jumpman is more than just a multi-billion-dollar subsidiary of the Swoosh: It’s a phenomenon that changed sports, culture, and commerce.

Not only did Nike and Mike establish an African American athlete as fashion’s most influential figure on the planet, but it also propelled other icons to take a stake in their likeness and turned Nike into a brand valued at over $190 billion today.

It almost never happened.

Coming out of college, a young Mike Jordan adored Adidas and was courted by Converse.

AIR, Ben Affleck’s latest feature film, tells the thrilling story of just how Jordan signed a deal with Nike that changed the course of history.

Prior to its 4/5/23 premiere — a serendipitous campaign coincidence — Boardroom got inside access from the Hollywood talent who depicted the power players in the game-changing contract.

Learn how those that were with the Swoosh from a spirited start-up to the dominant dynasty each influenced an industry.

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Sonny Vaccaro, Nike Basketball Marketing

David E. Klutho / Sports Illustrated via Getty Images

Accolades & Accomplishments

  • Formed the first high school basketball All-American Game, the Dapper Dan Classic.
  • Brought Michael Jordan to Nike.
  • Changed licensing in college sports by signing John Thompson, Jim Valvano, and Jerry Tarkanian to Nike contracts.
  • Founded ABCD Basketball Camp.
  • Discovered Kobe Bryant & Tracy McGrady, signing both to multi-million-dollar deals at Adidas out of high school.
  • Pioneered NIL by fighting the NCAA in the Ed O’Bannon case.

Few figures in sportswear are as impactful as the great Sonny Vaccaro.

At only 24 years of age, the Pennsylvania native founded the Dapper Dan Roundball Classic in 1965. With that, all of the country’s top high school talent — and college coaches — descended on Pittsburgh to see the best of the best play.

“It was the first All-Star game for high school kids ever,” Vaccaro told Boardroom. “Thirteen years ahead of the McDonald’s Game.”

Selling out the Civic Arena and forming friendships with the likes of Jerry Tarkanian, John Thompson, and Jim Valvano, Vaccaro came to be one of the most influential figures in the grassroots basketball scene simply by seeing ahead. In the late ’70s, he’d travel to Beaverton to pitch Nike on a basketball sandal concept he had prototyped.

Soon, Swoosh execs were so enthralled by his passion and personality that they instead offered him a job to sign shoe contracts with college coaches. Sonny’s scrappy approach and coach connections were enough to have 50 college programs sporting the Swoosh in NCAA action.

The next step was making a major splash in the pro game — an arena then dominated by Converse and Adidas.

“They were the underdog, which is such a weird way to think of Nike now,” Matt Damon, who plays Vaccaro in AIR, said on a Rotten Tomatoes panel. “But before this incredible deal, they were these renegade outsiders.”

Matt Damon as Sonny Vaccaro (Ana Carballosa / AMAZON CONTENT SERVICES LLC)

Leading up to the film, Sonny met Matt via Zoom. The two talked for well over an hour with the accomplished actor winning over the industry vet, who was already a fan.

“Him and Ben did Good Will Hunting when they were 12 years old,” Vaccaro laughs. “I watched every Jason Bourne movie and Rounders was a great movie. We talked and he asked me questions. He broke the ice by telling me he grew up five and a half blocks from where Patrick Ewing grew up.”

As fate would have it, Damon was a Georgetown Hoyas fan thanks to his proximity to Patrick. Ironically enough, it was Sonny who had John Thompson’s teams playing in Nike Terminator sneakers.

Once filming began, Damon invited Sonny and his wife, Pam, to the set to see it all in action. Sonny’s character is the star of the film, with his passion for basketball and intimate understanding of influence being key catalysts in signing the star that made the brand billions and inspired the world.

“I never would’ve imagined Matt or anyone of that ilk playing me in a movie,” Sonny says. “These are things you dream of.”

Rob Strasser, Nike Director of Marketing

Photo by Adidas
  • Led marketing on the original Air Jordan campaigns.
  • Dubbed the “MVP” of Nike’s turnaround in the ’80s by Phil Knight.
  • Launched Sports, Inc. consulting in 1987 with Peter Moore.
  • Joined Adidas and helped launch Equipment — or EQT — a line that still proves popular today.
  • Convinced Adidas to move its US headquarters from New Jersey to Portland.

Inside the offices of Nike, perhaps the only nickname more beloved than “Air” was “Rolling Thunder.”

Rob Strasser, the brand’s director of marketing for much of the 1980s, provided the intrinsic fire that made Nike cutting-edge in the era it sliced through.

“Rob was an incredibly passionate guy and was very selective as to who was going to intersect with Michael,” Kirk Richardson, who ran Nike’s SMUs at Foot Locker in the ’80s, told Boardroom in 2022. “It was very tight.”

The burly bearded man with a high-powered bullshit detector and boldness to push new ideas is depicted by the slightly slender, but also animated, Jason Bateman.

“You know, I don’t do a lot of research,” Bateman said at SXSW with a laugh.

Matthew Maher as Peter Moore, Matt Damon as Sonny Vaccaro, and Jason Bateman as Rob Strasser (Ana Carballosa / AMAZON CONTENT SERVICES LLC)

Truth be told, Bateman was already a teen icon as a child actor at the time Air Jordans were first coming out. Unknowingly, he was being influenced by the marketing prowess of Strasser.

“For people my age when Jordan came into the league and the shoes?” Bateman told the Rotten Tomotates panel. “I’m a big sports fan so that was a big draw.”

During media appearances, Affleck made it clear that Bateman was the only person who could play Strasser. He also shared that Phil Knight credited Rolling Thunder as the man who made the speech that helped seal the deal in signing Jordan.

“It’s an American business story, and they made a rock show out of that,” Bateman says. “They were somehow able to enhance what Michael Jordan means to us, which was already the zenith of greatness and excitement. I’ll never think of Michael Jordan or Air Jordans the same way again because of what Ben was able to do with that film.”

While AIR captures Strasser and Knight on the way to signing Jordan, Strasser’s brilliance shortly after was enough to plant the seeds for Jordan Brand that would sprout years later.

“We created a whole business plan to take Jordan out of Flight and it became Air Jordan,” Hill said. “That was intentional. Rob said it was so, so it was so.”

Eventually, Strasser left Nike and later worked at Adidas. While he sadly passed away at the age of 46, the passion of Rolling Thunder provided the electricity for both brands to explode in the ’80s and ’90s with work that still resonates today.

Phil Knight, Nike Founder & CEO

Jamie Squire / Allsport
  • Co-founder and chairman of Nike, Inc.
  • Forbes recently ranked as the 25th-richest person in the world with a net worth of $45.1 billion.
  • Ran track at the University of Oregon.
  • 2012 inductee to the Basketball Hall of Fame.
  • Decorated philanthropist and author.

When considering the cast and characters of AIR, few have more mystique than Phil Knight and none have more money.

The collegiate track runner turned shoe salesman is responsible for building one of the biggest brands in the world, completely revolutionizing sports, marketing, and innovation through his efforts.

A storyteller himself, Knight gave Affleck the nod and blessing that the movie was good by him.

“I showed Phil Knight the movie, which halfway through I realized might have been a gigantic mistake,” Affleck said at SXSW. “But he was enormously graceful. I’ve been there myself, I’ve been known to appear in the occasional meme, so I know that people like to make fun of the boss. That’s part of the workplace culture.”

For those fond of Phil’s footwear journey or familiar with Shoe Dog, AIR is not a one-to-one reproduction of the actual events that went into signing Michael Jordan. However, for Phil, it still felt right.

“He said, ‘Well, it didn’t exactly happen like that, but that’s the spirit.’ He had so much respect for Deloris and Michael,” says Affleck. “He said, ‘We were friends.'”

Deloris Jordan, Mother to Michael Jordan

Amy Sussman / Getty Images
  • Mother of Michael Jordan.
  • Key player in Nike negotiations and royalty arrangement.
  • Accomplished author and philanthropist.
  • Clinton Global Initiative Award winner in 2005.

In the 1950s, a young Deloris Peoples met her eventual husband, James Jordan, fittingly at a high school basketball game.

The prophecy of birthing the basketball business’s most influential icon would continue when the young couple moved to New York City and Deloris became a bank teller. By the summer of 1984, a match of her maternal instincts and the value she saw in her son culminated with her role in not only suggesting her son took a meeting with Nike but also signing a contract that empowered him and other athletes to follow.

Though the general public may not know the role of Deloris as prominently as the aforementioned executives, her famous son was well aware of the importance she had in the initial deal as well as what it meant to properly portray her in the film.

Image via Warner Bros.

“Michael Jordan is the most intimidating and impressive man you’ll ever see in real life,” Affleck said at SXSW. “I asked him about his mother and a look of reverence, awe, love, and gratitude came across his face. He said, ‘None of this would have ever happened without my mom believing in me.'”

In Affleck’s meeting with Michael, there was only one request: his mother must be played by the great Viola Davis.

“It was an honor to play Deloris,” Davis said at SXSW.

“Viola Davis is the best actor I’ve ever seen,” Affleck said. “I’ve never seen anything like it.”

When portraying Deloris, Davis leaned into the mother’s calm but confident demeanor.

“She is a study in Zen neutrality,” Davis said on the Rotten Tomatoes panel. “The woman is very, very steady and quiet.”

With that quiet confidence, Deloris was able to foresee just how much her son meant to her and what he would soon mean to the world.

“There was one person in the room who recognized that Jordan was going to be great,” Affleck said. “She recognizes that there must be some price to even be alone in that way. If there’s nobody else in the world like you? That’s a lonely feeling.”

David Falk, Agent to Michael Jordan

Image via Getty Images
  • Served as an agent to the likes of Michael Jordan, Patrick Ewing, Juwan Howard, and Allen Iverson.
  • Helped build both the Jordan Brand and Ewing Athletics through negotiations, leverage, and relationships.
  • Signed both basketball and apparel contracts for his clients that set records and shifted industries.
  • Largely considered one of the most powerful people in the history of sports and sportswear.

In the 2020s, a handful of power agents have become household names due to the 24/7 news cycle and deeper integration of business and sports.

In the 1980s and 1990s, one man defined the job and the industry — David Falk.

The super agent of all super agents, Falk found ways to turn NBA athletes into full-fledged superheroes. From Michael Jordan to Patrick Ewing, Falk’s clients raked in the dough on and off the court, having the endorsements and sizzle to engage an audience and promote products around the clock.

In the movie AIR, living legends like Phil Knight and Michael Jordan are less stars of the storyline and more pillars of the background.

Chris Messina as David Falk (Ana Carballosa / AMAZON CONTENT SERVICES LLC)

Falk, however, depicted by Chris Messina, steals the show. Like any agent of his era, it was not just the talking he did in the boardroom that made him a magnet for lucrative deals but the long-distance conversations he had from New York to Oregon that change the course of history.

“When I read it, I loved it,” Messina said on the Rotten Tomatoes panel. “But I was like, ‘Oh shit, this is a lot of phone calls.'”

As alluded to, many of Messina’s scenes in AIR have him yelling and yakking it up with Matt Damon who stars as Vaccaro. To make the magic come to life on screen, Affleck positioned each actor on opposite sides of the same set to amplify the chemistry.

“We got to do those phone calls at the same time,” Messina said at SXSW. “Matt and I were down the hall from each other with three cameras on each of us and Ben would go back in forth. To do it together was a blast.”

Though Messina may have a drastically different hairstyle than that of the chrome dome Falk, the intensity he brings channels the same spirit of the accomplished agent that changed the game through the Jordan x Nike deal.

“The majority of players who have endorsement relationships simply get paid to wear shoes,” Falk told Boardroom in 2022. “The elite players, since Michael, have their own signature.”

Howard White, Nike Sports Marketing

Ethan Miller / Getty Images
  • Played basketball at the University of Maryland for Lefty Driesell.
  • Worked for Nike in the late ’70s & ’80s as a field representative, developing relationships with athletes.
  • Played a major role in recruiting Michael and the Jordan family to Nike.
  • Helped introduce and launch the Jordan Brand.
  • Currently resides as Vice President of Jordan Brand.

Years before the NBA adopted the idea of nickname uniforms, a basketball star at the University of Maryland was ahead of the game.

Howard White, better known as “H,” had his introductory initial embroidered on the back of his Terrapins game uniform in quotes instead of his last name. If that serves as any indication of the level of sauce and influence this man possessed, it would all arise in AIR, played perfectly by Chris Tucker.

“Howard White is a good friend of mine,” Tucker said at SXSW. “He helped me out so much and he really schooled me.”

Image via People

A larger-than-life personality despite working behind the scenes, the man MJ calls “H” helped nurture the very important relationship between the Jordan family and the Nike brand in the early days of the deal. Since then, he’s played pivotal roles in both building and expanding the Jordan Brand, recently assisting in the signing and storytelling around No. 1 draft pick, Paolo Banchero.

His knack for relationships spans much further than sports, making his existing friendship with Tucker the chance to take his on-screen portrayal to another level of research and excellence.

“I had all access to him and everybody he mentored like Charles Barkley,” Tucker told a Rotten Tomatoes panel. “I had people from his childhood he played hopscotch with and teachers and coaches. I got a lot of information together to embody his spirit and dialect.”

Though White’s outsized excitement makes him command a room from the start, it’s his optimism that makes him beloved by ballplayers, businesspeople, friends, and family.

“Everybody said he was like Confucious,” Tucker says. “This nice guy who thought about the world as a glass half full, not half empty.”

Peter Moore, Nike Creative Director

Photo by Adidas
  • Served as the first-ever Creative Director at Nike.
  • Designed the Air Jordan 1 and the Nike Dunk.
  • Created Nike’s most memorable posters of the 1980s.
  • Launched Sports, Inc. consulting in 1987 with Rob Strasser.
  • Played a part in crafting brand identities for athletes like Jordan, John McEnroe, and Dikembe Mutombo.
  • Joined Adidas and helped launch Equipment — or EQT — a line that still proves popular today.

Search StockX or pull up at Foot Locker and you’ll find the fingerprints of Peter Moore’s pen all over the industry.

In 1976, Moore began doing creative consulting work for Nike by way of his own agency. Soon enough, he was in the house as the brand’s first creative director. A decade after his first gig at the Swoosh, he designed the two most popular basketball shoes in the NBA and NCAA, both of which are billion-dollar entities themselves in 2023: the Nike Dunk and the Air Jordan 1.

“Peter Moore had a vision for a brand,” Brad Johnson, former Nike Basketball Product Line Manager, told Boardroom in 2022. “Peter and Rob were like two peas in a pod and they knew that once we signed Jordan and this started steamrolling that Nike had something really special.”

In AIR, actor Matthew Maher portrays Moore as an engineer who’s both eclectic and astute.

Matthew Maher as Peter Moore (Ana Carballosa / AMAZON CONTENT SERVICES LLC)

Due to Moore’s death in 2022, Maher had to research the lost legend.

“Peter Moore had just passed away a week before I was offered the role in the movie,” Maher said on a Rotten Tomatoes panel. “I dived in, read a lot about him, and watched documentaries in which he was featured. What struck me was looking at his designs and ideas that were so amazing ahead of their time, but when he was talking? He’s just a regular guy! He’s talking about, ‘There was too much red and we just decided to leave it that way!’ He was very direct.”

While the person who made the Air Jordan 1 fly was Michael himself, Maher found a common thread behind the basketball brilliance of MJ and the design prowess of Moore when researching his subject.

“The biggest parallel was listening to pro athletes talk about what they do,” Maher says. “A genius does not always express themselves very well when he’s talking about what he’s genius at. He is a genius, but he’s at a crossroads in his life. He’s going through a midlife crisis where he’s waiting for something to come along where he can really apply himself.”

With the Air Jordan 1 and its icon campaign, Moore did all that and, well, more. His ability to be stubborn enough to believe in unique ideas but fluid enough to work with others gave him the ability to build Nike in the ’80s and later a new generation of Adidas in the ’90s — to include Kobe Bryant’s signature line with Audi.

“He’s a brilliant collaborator,” says Maher. “He’s not precious about his ideas. The idea itself is bigger than he is.”

George Raveling, Team USA Assistant Coach

Bernstein Associates / Getty Images
  • Played basketball at Villanova.
  • First African American coach in the ACC at Maryland as an assistant under Lefty Driesell.
  • Coached Michael Jordan in the 1984 Summer Olympics.
  • Head coach at Washington State, Iowa, and USC.
  • Worked at Nike as Director for International Basketball after his coaching career.
  • Inducted into the Basketball Hall of Fame.

At Villanova University, the 6-6 Raveling starred as a forward.

Three years after graduating, he’d become famous for playing guard.

Accidentally attending Dr. Martin Luther King’s I Have a Dream speech due to persuasion by a parent, Raveling ended up serving as security for King on stage. His height and assertiveness to volunteer empowered him to ascend to the right place at the right time, getting gifted a copy of the speech from MLK himself — something he still holds to this day.

That timely nature and strong stature made Raveling revered on the college coaching circuit throughout his career, forging a relationship with a young Michael Jordan when the two represented Team USA under head coach, Bobby Knight.

For his influence and relationships, Raveling became one of the most pivotal college coaches to sign a shoe deal with Nike and also a conduit for the original Jordan deal getting done.

Marlon Wayans as George Raveling (Ana Carballosa / AMAZON CONTENT SERVICES LLC)

Though his screentime in AIR is short, his tenure with the Swoosh was long and impactful. Working for years as an executive at Nike, his thematic portrayal by Marlon Wayans depicts a meeting at Tony Roma’s in Los Angeles in which the coach connects dots for the deal that changes the course of history.

“He was a fantastic man,” Wayans said on a Rotten Tomatoes panel for the film. “He coached on the Olympic team. I read the monologue and the fact that that was real? That he still has the I Have A Dream speech in his possession? At a young age, he was at that rally. He had a long career of [activism].”

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Ian Stonebrook

Ian Stonebrook is a Staff Writer covering culture, sports, and fashion for Boardroom. Prior to signing on, Ian spent a decade at Nice Kicks as a writer and editor. Over the course of his career, he's been published by the likes of Complex, Jordan Brand, GOAT, Cali BBQ Media, SoleSavy, and 19Nine. Ian spends all his free time hooping and he's heard on multiple occasions that Drake and Nas have read his work, so that's pretty tight.

About The Author
Ian Stonebrook
Ian Stonebrook
Ian Stonebrook is a Staff Writer covering culture, sports, and fashion for Boardroom. Prior to signing on, Ian spent a decade at Nice Kicks as a writer and editor. Over the course of his career, he's been published by the likes of Complex, Jordan Brand, GOAT, Cali BBQ Media, SoleSavy, and 19Nine. Ian spends all his free time hooping and he's heard on multiple occasions that Drake and Nas have read his work, so that's pretty tight.