When Allen Iverson was drafted first overall by the Philadelphia 76ers in 1996, the city braced itself for something new, something big. And Iverson didn’t just bring his talent, he brought a nickname—The Answer. While the nickname was based on the bulldog tattoo on his arm with “The Answer” inked above it, the origin of the story of the name remains somewhat of a mystery.

A common perception was that AI could serve as an answer to the NBA and 76ers’ problems. But it served another purpose as well. Reebok paid an ode to the nickname by naming their first Iverson sneakers as “Reebok Question” while all subsequent sneakers were called Answer except for subsequent variants of the first sneakers.

More about the history of Allen Iverson sneakers that started with Question

In the mid-1990s, Reebok was at a crossroads. They needed a spark, someone who could bring the brand to life and stand toe-to-toe with the competition. But not just any player would do—they wanted a fresh face, someone relatable and charismatic. And that’s when they found their star in Iverson. Imagine it—a young guard from Georgetown, standing barely 6 ft tall, yet electrifying crowds with his speed, his swagger, and his streetwise style.

AI wasn’t just a basketball player—he was the embodiment of hip-hop culture. The guy you’d see in oversized clothes, chains, and a fearless attitude that spoke directly to a generation. When the Philadelphia 76ers picked Iverson first overall in the 1996 NBA Draft, fans knew something big was coming. At only 21, Allen Iverson was suddenly the name on everyone’s lips. And it wasn’t just because he was the top pick.

His on-court highlights were mind-blowing—the kind that made you lean forward on your couch. If you’ve ever seen clips of him breaking ankles with that crossover or slashing his way to the rim, you know he played with confidence and style all his own. It wasn’t long before he claimed Rookie of the Year, solidifying what many already suspected—AI wasn’t just a star, but a player changing the game.

With the 76ers star’s unmistakable appeal, Reebok knew they had to create something iconic. And that’s when they launched the Reebok Question. Now, if you remember the original Red Toe colorway, you know it was love at first sight. The shoe wasn’t just functional, but stylish and bold, just like Iverson. That flash of red on the toe caught everyone’s attention, making AI impossible to miss on the court. In a way, the Reebok Question was the perfect extension of him. A little edgy, highly memorable, and totally unique.

Iverson’s first deal with Reebok and the deal that saved him

The Philadelphia 76er star’s decision to sign with Reebok is a classic tale of a bet that paid off beyond anyone’s expectations—especially for the Philadelphia 76ers star himself. In 1996, as the number one draft pick for the 76ers, he inked a 10-year, $50 million contract with Reebok. Who would’ve thought that years later, this partnership would be his saving grace?

In 2001, Iverson’s talent and dedication took him and the Sixers to the NBA Finals. That same year, he earned the MVP title, and Reebok knew it was time to make things permanent. The 11x All-Star scored a lifetime deal with the brand. A move that would go on to support him during his financial struggles. Throughout his career, AI managed about $100 million—$155 million from his NBA salary and another $40-50 million in endorsements.

But with Allen Iverson, it was never just about him. He was known for rolling with an entourage that sometimes hit 50 people. If you were in his circle, you were taken care of. Friends and family, especially his mother, were treated to cars, jewelry, houses, and luxurious vacations. But as you might guess, that lifestyle took a toll. Not only did he fund a king-sized lifestyle for himself and everyone around him, but he also reportedly stored his money in dozens of garbage bags around his mansion.

And yes, some bags disappeared. Al’s financial troubles weren’t just bad luck—they were fueled by habits that were hard to break. In one infamous story, he forgot where he parked his car at the airport and decided to just buy a new one. So, it’s no surprise that eventually, he faced bankruptcy. And that’s where Reebok’s lifetime deal came in.

In addition to the yearly $800,000 payment, Reebok had set aside $32 million in a trust fund that Iverson can’t touch until he turns 55 in 2030. But the Reebok story doesn’t end there. Allen Iverson’s role with the brand has only grown. Recently, he stepped up as Reebok’s vice president of basketball, working alongside Shaquille O’Neal, who leads the division. Clearly, what started off with a Question from Reebok has been The Answer to a lot of Al’s problems.