The Bulls would go on to win that game (and another championship a few short months later), but that was merely subtext. The headline was Iverson staking his claim in the league against the very best, in a way only he could.

When Iverson was entering the 1996 NBA Draft, he had a decision to make. He was being courted by sneaker companies and it became quickly apparent that it would come down to two suitors: Nike and Reebok.

At Georgetown, Iverson was always draped in Nike. Georgetown has always been a Nike school, and coach John Thompson sat on Nike’s Board of Directors. During Iverson’s two years on campus, he could be seen wearing everything from Jordan XIs to Nike Way Ups, Air Unlimiteds, or Air Up Highs. After hiring David Falk as his agent in 1996, all signs were starting to point towards Nike.

But Falk, despite his deep ties to Nike and his personal relationship with founder Phil Knight, knew it was the smart thing to wait and see what Reebok had to offer.

Reebok was in need of a superstar, an athlete that could carry the brand going forward. Nike had a firm grip on the sports apparel landscape in the mid-1990s. Jordan was, of course, the top dog, but the rest of the Nike basketball roster read like a who’s who of the All-NBA team. Despite potentially receiving his own signature shoe, Iverson would never be top dog at Nike. “They wanted Allen,” said Falk in an in depth oral history with Nice Kicks. “But they weren’t prepared to step up to the level that it was going to take to sign him.”

First, Reebok put its money where its mouth was. The company offered Iverson $60 million over 10 years. “It was the highest guarantee that anyone had ever gotten in shoes,” said Falk. Despite Coach Thompson’s role with Nike, he told his prized pupil that it was a no brainer.

Then, Reebok wanted to not only be aggressive in its marketing of Iverson and his signature shoe, but package Iverson just as he was. “All along, Reebok told me they didn’t want to make me up,” Iverson remembered. “They wanted to let me be myself.” Given how celebrated Iverson has been for both the league and self-expression within the league, this was some incredible foresight on Reebok’s part.

In addition, Reebok was ready to go with a signature shoe right out of the gate, The Reebok Question, which immediately appealed to Iverson.

“When you’re a kid and you’re a sneakerhead like me and you have all these dreams and aspirations,” Iverson said in an interview with Sneaker News, “there are no words that can explain how I feel about it because I’m just overwhelmed with the fact that I had a signature shoe. It’s actually ‘my shoe.’”

Reebok had created The Question before Iverson even officially came on board, and were so confident that it would be a groundbreaking basketball shoe, that they’d put it on (other Reebok athletes) Kenny Anderson or Nick Van Exel if the Iverson deal didn’t work out. Once it became clear that Iverson was about to join the Reebok roster, they began pitching sneaker stores on the potential of this groundbreaking shoe and their new trailblazing athlete.

“When we designed it,” Todd Krinsky, Vice President of Reebok, recalled. “It was really all about performance. We wanted it to be about speed, and we wanted it to have elements of speed to it.”

The Scott Hewett-designed Question featured a speed ghilly lacing system--much like the Jordan XI Iverson wore while at Georgetown--with the Reebok branding on the sides. They added a splash of color on the toe because Iverson moved so quick that they wanted something to pop while he was moving. Hewett added Hexalite cushioning windows on the midsole, a translucent outsole and the Question logo on the heel.

The shoe was an instant smash both on and off the court. Iverson came out of the gates on fire during his rookie campaign and was easily the most impressive rookie from one of the greatest drafts in NBA history.

Off the court, The Question was already becoming a legend. Originally released in the fall of 1996 with a retail price of $99.99, Reebok could only get limited pairs into the marketplace due to the timing of Iverson’s signing with Reebok and the final confirmation of The Question’s design. Due to those production restrictions, Reebok initially only put the shoe in the Philadelphia, D.C. and New York markets.

“When we first put them out, I started getting phone calls in the morning that kids were coming in right after school and that the shoes were almost sold out,” said Krinsky. “We started hearing stories from the store employees that kids were coming from Delaware and Boston, driving 3-4 hours to go to the Philly store to get the shoe. After the second day, it was completely sold out.”

Iverson’s career had just begun, and Reebok put out a shoe that retailers weren’t completely sold on initially, and they still flew off the shelves. Iverson clearly possessed something special.

Retailers began to beg for more pairs, but more importantly, Iverson’s team at Reebok knew that he had permeated culture and was catapulting Reebok amongst the youth. They now had relevance in a market where they previously had none.

“Allen Iverson has already paid for his investment,” said John Borders, former Reebok Vice President in a 1996 statement. “He’s already earned every dime we’ve given him. We’re a struggling company. We didn’t connect with a young audience. That’s where Allen helped us.”

After initially releasing the Question in two colorways (White/Red and White/Blue) in the fall of 1996, more colorways began to emerge over the ensuing seasons. White/Black and Black/Gold colorways emerged in 1997 (as the Sixers switched from their traditional red, white and blue colors to a more modern black and gold design). In the 22 years since the shoe’s original release, Reebok has pumped out nearly every colorway imaginable of the Question. There have been releases chronicling the other stops in his NBA career, most notably Denver. There have been collaborations with sneaker boutiques like Packer Shoes and Sneakersnstuff. There are even colorways commemorating his various accolades, like his Hall of Fame induction or his number being retired in Philly. More recently, sportswear designer Eric Emanuel has given his own “Pink Toe” treatment to the classic Reebok Question. As Emanuel has often relayed in interviews, Iverson’s attitude and public panache made him a key style icon in the designer’s formative years.

The Iverson line would go on beyond the Question, eventually releasing 14 signature sneakers to varying success. The first few iterations of The Answer sneakers (this is the series that would ultimately become Iverson’s yearly, recurring sneaker line post-Question) would continue to sell well as Iverson was becoming one of the league’s best and most popular players.

Where some people viewed Iverson’s perceived missteps as a liability, Reebok banked on Iverson’s unapologetic nature being what set him apart from his peers. Just in his draft class, Jordan Brand had invested in Ray Allen to be the standard bearer for the company once Jordan decided to hang it up. Kobe Bryant was tapped by adidas to be the new face of its basketball line. Both were packaged as clean-cut in the Jordan mold back in 1996, but Reebok put all its eggs in the Iverson basket and was rewarded mightily for its foresight.

Understanding culture has always been paramount for Reebok. This is, after all, the same brand that took a chance on a rapper, Jay-Z, selling a sneaker before it became industry standard and it’s the same brand who entrusted Swizz Beatz to be its creative director. But its most important decision was going all in on Iverson 20 years ago.

Reebok rewarded Iverson with a lifetime endorsement and marketing contract in 2001, on the heels of his greatest season as a pro, having captured the MVP Award and leading the 76ers to the NBA Finals. The lifetime deal awarded Iverson $800,000 annually and includes a $32 million trust fund that he can access when he turns 55. So even as the company turns its focus more towards CrossFit and UFC, Iverson will continue to remain one of the most important faces of Reebok, long into his retirement.

The crossover helped create The Question’s mystique. Every great sneaker has an accompanying moment that helps etch its place in the cultural landscape. The Jordan III had the free-throw line dunk. The Jordan IV had “The Shot” against Cleveland. The Question crossed up Michael Jordan, which not only created an ultimate “WOW” basketball moment, but symbolized a passing of the torch in the process. Jordan would soon be on his way out. A new era, led by Iverson, was ready to take the league and run with it.

The NBA and its legion of worldwide fans found an unlikely hero in Iverson. In many ways, he was the anti-Jordan. Unapologetically honest, authentic and true to his Virginia roots, he instantly became a trailblazer. Whereas Jordan’s image was carefully crafted, Iverson was more take it or leave it. And for a generation of sports fans who identified with his struggle and story, or just simply loved him for being “him,” he won the adoration of fans all around the world in ways only his idol seemed to rival.

“It’s one of the only shoes that sold equally well in both the suburbs and urban areas,” recalled Krinsky when reflecting on the success of The Question. “The shoe itself was really clean and wearable, and also Allen transcended all barriers. Kids all over the world loved him because of his heart, his fearless play, and his size. Those attributes are universal.

“You don’t have to be from the hood or from the suburbs to respect a kid that’s 6’1, 165 pounds giving it his all every night. That’s just universal. I think Allen himself meant all sorts of things to different people for different reasons.”