30 (tie). CC Sabathia – New York Yankees, Major League Baseball:
Sabathia signed a seven-year, $161,000,000 averaging $23,000,000 a year and $141,975.31 a game in December 2008. The contract was then a record for the biggest pitcher deal in baseball history.
It paid off immediately as New York won the World Series in 2009. Sabathia is a six-time All-Star. He experienced some injuries in the middle of his run with the Yanks but has gotten back on track the past three seasons. A huge deal that was worth it.