1. Cliff Lee (2011-2014) Five-year $120 million
Cliff Lee dominated for the Phillies when we traded for him in 2009 and he won two games in the World Series. Even with the late Roy Halladay coming over, Philadelphia fans were still mad that we traded Lee to the Mariners. Lee turned down a much larger contract from New York to return to Philadelphia and formed the Phantastic Phour with Halladay, Roy Oswalt , and Cole Hamels. Over his last four years in Philly, Lee went 41-30 with his best year coming in 2011 when he went 17-8.
Lee was one of several signings that helped the team win early on in the last decade.