#19: Sugar Ray Robinson
Many experts still call Sugar Ray Robinson the greatest boxer who ever lived. He won five middleweight titles and became a Harlem celebrity, driving a flashy pink Cadillac and owning a nightclub and other businesses. Wherever he went, a big crowd of helpers followed. So did the bills.

By the time he retired in 1965, most of his fortune was gone, and he owed back taxes. Robinson turned to nightclub acts and small acting roles to earn money. He later started a youth foundation in Los Angeles to help kids, and he died in 1989.
