Shane Mosley: $10 Million
Sugar Shane Mosley engaged in battles with some of the biggest names in boxing throughout his 61-fight career. He defeated Oscar De La Hoya twice and held four championships in three weight classes. His showdown with De La Hoya made him an instant millionaire, with earnings of at least $15 million, his highest from a single bout. Mosley exchanged blows in high-profile matches against Winky Wright, Miguel Cotto, Floyd Mayweather Jr., and Manny Pacquiao.