O.J. Simpson |Est.$ 3 million

O.J. “The Juice” Simpson is considered one controversial athlete in the entire history of sports. He is best known for his great success as an NFL player and making several attempts to enter the entertainment business. In recent years, the football sensation has been more identified with his involvement in the highly-publicized trial, where he was eventually acquitted.

Despite it all, Simpson is slowly regaining his footing, and he has even maintained an estimated net worth of $3 million after he was granted parole in 2017. As attorney’s fees did not come cheap, nor did the settlement, Simpson’s earnings were damaged to an irreversible degree. Sadly, all of his hard-earned money went down the drain. Although he still can earn a pension from the NFL, it is definitely going to be hard to recover from his financial ruins now, at 72 years of age, with nearly $ 40 million of debt still owed.