10. Glenn Robinson
Robinson had a stellar college career at Purdue and entered the NBA Draft in 1994. His contract negotiations with the Bucks are the stuff of legend. That’s because he demanded an outrageous sum of money from the team. The franchise resisted but in the end, they agreed to give the rookie a ludicrous $100 million deal. It’s impossible in the modern day but the 1990s were a wild time.

Furthermore, they guaranteed every dime of the contract. Robinson was the winner because he wasn’t a $100 million player at the time. He became a two-time All-Star but he had a reasonably average career. Finally, he won a Finals ring when he moved to the Spurs in his last season as a professional. He achieved a lot and made a fortune (via Chicago Tribune).