Football player Arch Manning has the highest NIL valuation of $6.5 million! Critics worry that name, image, and likeness deals upend amateurism—yet few trace its roots back to one unconventional path. Long before Caitlin Clark and Bronny James, one NBA hopeful bent the rules and set a precedent. A former NBA player even once took credit for opening up doors for future players. He even credited the former Nike executive, the legendary man behind Michael Jordan’s historic shoe deal for the success.

Before digging into the past, in the present, we see Lakers player Bronny James, who is the highest-paid student-athlete in this recently created NIL history. He had an On3 NIL Valuation of $4.9 million, thanks to his deals with PSD Underwear, Nike, Beats by Dre, and more! Speaking of women’s college basketball and its growing popularity, Caitlin Clark had an NIL valuation of $3.1 million. She had a long list of brand deals, with some of the notable names being Nike, Gainbridge, Gatorade, State Farm, Xfinity, Buick, and more.

It has paved the way for others as well. But who sparked the idea first by bending the rules? “I’m happy about it. I mean, I’m technically, I’m the reason why… if you think about it, I was the first one to go overseas,” former NBA player Brandon Jennings said on the Captain Jack podcast. Jennings was a true trailblazer! When the NBA posed a big challenge to the former high school standout, he opted for an unconventional route. In his recent interview with DJ Vlad, the former Milwaukee Bucks shared that the master man behind their plan was Sonny Vaccaro.

Unsure of whether his academic grades are good enough for him to get into Arizona, Jennings called Sonny Vaccaro. “I couldn’t get into Arizona, I called Sonny about going overseas, so Sonny is the reason why I started this whole NIL thing, and I signed to Under Armour,” he recalled. “I think we’re going to have a revolution, and Brandon Jennings, a kid from Compton, is going to start it,” Vaccaro once said as per the New York Times. Sonny guided him throughout the time and even expressed intrigue at how parents of players approached him to guide their kids to follow the same path. 

Here is what forced Jennings to take a different journey to the NBA. To encourage more players to compete at the college level, David Stern and NCAA President Myles Brand established the one-year rule, which required draft prospects to have at least a one-year gap after high school before entering the NBA. College players weren’t making much, so Jennings decided to take his talent to Italy and became the first American to play professionally in Europe

Throughout that year overseas, Vaccaro continued to mentor Jennings, arranging high‑level exposure at showcases like Impact Basketball in Las Vegas and fielding calls from parents interested in similar paths. This Under Armour collaboration cemented Vaccaro’s role not just as a shoe‑deal guru but as a trailblazer for unconventional pre‑NBA paths, making him the pivotal figure behind Jennings’ early career and the modern NIL paradigm

Jennings signed a €1.65 million (net) contract with Lottomatica Roma—roughly $2 million—becoming the first American in Europe and landing Under Armour’s inaugural basketball deal. But was Jennings Vaccaro’s only superstar?

Sonny Vaccaro and Michael Jordan:  A spark that started it all 

When thinking of what Vaccaro and MJ accomplished, we go back to 1984, when the historic deal with Nike emerged. This deal not only propelled the company to unprecedented heights but also helped Michael Jordan become the legend he is today. Vaccaro was the crucial link between the two. He watched a 19-year-old’s awe-inspiring 16-foot winning shot and decided to bet his career on him. There were other important members, Rob Strasser, George Raveling, and more, who made this deal happen, but Vaccaro’s role in it was unique.

He first saw Jordan, then the freshman led the North Carolina Tar Heels to the 1982 NCAA championship with his clutch shot. That changed everything for him. Initially, the Bulls player wanted to sign with Adidas, but after just one meeting, the former Nike executive managed to change his mind. Vaccaro wasn’t known for making great first impressions, but he had his own unique approach. 

At that time, Jordan was a talented rookie. When Vaccaro couldn’t convince him directly, he decided to approach his parents, especially Jordan’s mother. And that strategy proved successful. It was his parents who convinced MJ to attend at least one meeting, and he agreed.

From the proposal to the offer of his signature shoe line, Jordan was impressed. This became one of the biggest deals in the history of sports and sneakers. The film Air tells the true story of Vaccaro and his efforts to realize this deal, with his character portrayed by Matt Damon. After leaving Nike, Vaccaro joined Adidas and Reebok, where he went on to sign other incredible players such as LeBron James, Kobe Bryant, and more. A business acumen unlike any other.