18. CC SABATHIA $23 million
Photograph By Kim Klement/USA TODAY Sports
The seven-year, $161 million contract he signed with the Yankees in 2008 was the largest ever for an MLB pitcher. Sabathia finished his first season 19-8 with a 3.37 ERA as the Yankees won the 2009 World Series. In October 2011, Sabathia decided not to opt out of his deal and signed an extension that added an additional year at $25 million.