7. CC Sabathia: Seven Years, $161 Million
The crown jewel of the 2008-09 offseason, and the pitcher the Yankees had to have.
He did everything asked of him and more from 2009-2012, throwing 230+ innings from '09-'11 and winning a title as the ace of a three-man staff in his first season in the Bronx. Glad he decided he preferred the cold weather and pressure in New York to a long-term California home.
Eventually, Sabathia battled sobriety and struggled as he aged, but pulled things together spectacularly to post a second exceptional run with the team from 2016-19, serving as the veteran leader on a staff of newcomers (and passing the 3,000 strikeout plateau).
He's destined for Cooperstown. The only issue is exactly how many fools hold his 3.74 ERA against him and how long we'll have to wait.
And now, for a player the Yankees hope will eventually pick a thing or two up from Sabathia...