21. Derek Jeter – New York Yankees, Major League Baseball:
Jeter signed with the Yankees for 10 years and $189,000,000 after they drafted him in the 1992 draft and he played for six successful years. The deal averaged $18,900,000 a year and $116,666.67 each game.
It’s beyond safe to say the deal was worth it. Jeter played his entire 20-year career with the Yankees, batting .310 with 3,465 hits, 260 home runs, and 1,311 RBIs. He’s also the Yankees’ all-time leader in hits, games played, stolen bases, plate appearances, and at-bats. He also hit .321 in the World Series.