Estimated earnings: $300-400 million.
Mike Tyson was one of the biggest heavyweight champions in the 1980s and 90s. He was the youngest man to win the WBC, WBA and IBF Heavyweight.
Over his entire career, he amassed between $300-400 million. He started throwing all his money at mansions, luxury cars, and even a pet tiger.
But after his wife accused him of domestic violence which led to a divorce, the death of his trainer, and several charges of rape, possession of drugs, a DUI, and biting Evander Holyfield’s ear, his career was headed straight for the toilet. He owed more than $13 million to the IRS and lost $9 million in a divorce settlement. At one point his estimated worth was less than $700, and he was headed towards bankruptcy.