45. Zack Greinke – Los Angeles Dodgers, Major League Baseball:
Greinke signed a six-year, $147,000,000 deal with the Los Angeles Dodgers in late 2012 that averaged $24,500,000 a season and $151,234.57 per game. At the time, it was the biggest in MLB history for a right-handed pitcher. He delivered on that deal but didn’t pitch out his full contract.
He opted out of the final three years of the agreement after a stellar 2015 season. Greinke was named the Outstanding National League Pitcher at the Players Choice Awards before signing another massive deal on this list to be discussed later.