Freddie Roach: $20 Million
Before becoming the acclaimed trainer for Manny Pacquiao and Miguel Cotto, Freddie Roach had a career as a professional boxer himself. His highest payday in the ring was $7,500, but he was forced to retire at the age of 26 due to early signs of Parkinson's disease. Despite the condition, Roach has become one of the most respected trainers globally and shows no intention of slowing down. Interestingly, actor Mickey Rourke enlisted Roach to train him during a career change in the early '90s.
