32 (tie). Manny Ramírez – Boston Red Sox, Major League Baseball:
Ramirez signed an eight-year, $160,000,000 contract that actually ended up being 10 years and $200 million with Boston in December 2000. The deal had options for two final years averaged $20,000,000 a year and $123,456.79 a game.
He was looking for a straight-up 10-year contract from the start. But it didn’t matter. Ramirez became a Red Sox legend. Over his career, he hit .312 batting average, 555 home runs, and 1,831 RBI while helping Boston finally win the World Series. Great deal.