John McEnroe

McEnroe was one of the greatest players of his generation, despite his combative on-court conduct. He won seven Grand Slams in his career, including 77 singles victories and 78 major titles, and his 1984 season record of 82-3 is still the best single-season victory rate.

While McEnroe's on-court antics got him into controversy with match officials, they also turned him into a brand magnet. McEnroe ranks among the all-time wealthiest tennis players, having promoted brands like Nike, Mercedes, American Express, Bic, Dunlop, and Sergio Tacchini.

Career: 1979 – 1992

Net Worth: US $100 million

Sponsors: Dunlop, Sergio Tacchini, Nike, Bic Razor, American Express, Tesco, Mercedes, Heineken, Seat Altea