#6 Allen Iverson (1996) – Reebok, 10 years/$50 million
Value in 2019: $81,626,195.03 in 2019 or $8.2 million/year
AI was known as a one of NBA's most tenacious scorer and competitor, even surprising everyone by leading the Sixers to a Game 1 win over the heavily-favored Lakers in the 2001 NBA Finals.
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'The Answer' earned over 200 million dollars throughout his NBA career, including millions of dollars from various endorsements outside of sports apparel. Despite this, however, he was famously reported in 2012 to have spent his money unwisely to the point of having owed almost a million dollars to a jewelry store and being banned from casinos in Detroit and Atlantic City.
Iverson's deal with Reebok, however, extended far beyond the guaranteed 10 years he initially signed as a rookie. In 2001, Reebok had a unique agreement with the dynamic guard, setting aside $32 million in a trust fund that he could only touch when he's 55 years old. Until then, AI would have to make do with the annual $800,000 lifetime payment by Reebok. Not bad for a retired superstar.
#5 Ben Simmons (2016) – Nike, 5 years/$20 million plus $20m in bonuses
Value in 2019: $42,689,254.90 or $8.5 million/year
Australian star Ben Simmons signed a 5-year, $20 million contract coming into the NBA as the undisputed number 1 pick in the 2017 NBA Draft. The contract was also reported to have an additional 20 million dollars in incentives, most provisions of which were reportedly very much achievable by the LSU product, such as winning All-Rookie Team honors and winning Rookie of the Year. The other provisions were much more difficult, like being selected All-NBA and winning MVP. But for the most part, the deal was so lucrative that it pushed incentives to over $20 million.
This should come as no surprise though, as the 6'10 point guard is a generational talent that has since won Rookie of the Year, been selected as an All-Star, and has helped his team get to the Eastern Conference Finals at just 23 years old. He attracted several other endorsements even before playing his first NBA game, including Foot Locker, Beats by Dre, and Upper Deck, and Nike was more than willing to attract the young star to be part of their brand.
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