5. Oscar De La Hoya

Career Earnings: $150M
Net Worth Now: $175M
Sport: Boxing

This one's a little tricky. Oscar made a lot of money on the back end of his career thanks to big money fights against Pacquiao and Mayweather; he was basically done by then. He cashed in then threw in the towel. Nowadays he's running the top boxing promotions company and running it well. Golden Boy Promotions consistently puts out fights fans want to see and he put fellow boxers, Bernard Hopkins, Shane Mosley, and Marco Antonio Barrera down as partners. The Golden Boy has a lot more cash to make.