14. Clinton Portis
Portis enjoyed seven seasons with the Washington Redskins after playing for the Denver Broncos. A two-time Pro Bowl selection, he had superb physicality and power on the playing field, amassing over 12,000 yards in his career. Furthermore, he brought home bags of cash from a productive career that saw him make over $50 million in salaries alone. However, the age-old story of bad investments brought him to his knees.
The IRS, dependent women, and casino debts all piled up and punished Portis. Things got so back for the former NFL star that he even confessed that he considered killing his snake-oil salesmen financial advisors. Luckily for him, he was able to control this impulse. It wouldn’t have helped him regain the millions of dollars that he had lost anyway. But he paid a heavy price.