Joe Louis is considered by many the greatest heavyweight boxer of all-time. He held the title for over 140 months, the longest stretch of anyone in boxing history. Unfortunately, the 'Brown Bomber' couldn't punch his way out of deep tax debt.

When Louis became successful, the top income tax level was 79%, and then during WWII, it rose as high as 90%. Louis donated money from two fight purses to the Navy Relief Fund and the Army Relief Fund, but those contributions were unable to be deducted, further complicating his tax problems.

After his initial retirement, Louis' debt forced him to attempt a comeback in 1950, but with a 90% tax rate, the comeback would not solve his financial woes. By the end of the '50s, Louis owed over $1 million in back taxes. In attempts to make money, Louis turned to professional wrestling and appearances on quiz shows. Finally, Louis even took a job greeting tourists at Caesar's Palace in Las Vegas to try to pay down his debts.

Top 10 Worst Athletes to Ask for Financial Advice