Sugar Ray Leonard: $120 Million

Sugar Ray Leonard, a pivotal figure in boxing from 1977 to 1997, was part of the iconic "Fabulous Four" alongside Roberto Duran, Thomas Hearns, and Marvin Hagler. He helped elevate the popularity of lower weight classes after a period dominated by heavyweight stars like Muhammad Ali. Leonard was the first boxer to surpass $100 million in earnings. Following his boxing career, Sugar Ray transitioned to a successful role as a boxing analyst and commercial spokesperson, maintaining an exceptionally high income. He retired with 36 wins, three losses, and one draw.

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