Bjorn Borg
Famed for his tennis matches against John McEnroe, Bjorn Borg won his first Wimbledon at 20 years old. Retiring at 26, Borg lived in luxury, spending tons of money on his friends. He lived in Monte Carlo to escape the $40,000 in back taxes he owed in Sweden. After three marriages and two divorces, Borg went bankrupt in 1997.