Cliff Lee
Lee’s career had many unexpected twists and turns. The southpaw had established himself as a dominant pitcher for the Indians, leading the league in wins and taking home the Cy Young in 2008 after having been sent back to the minors just the year before.
Despite this success, the Indians traded him during the 2009 season with Ben Francisco to the Phillies for Jason Knapp, Carlos Carrasco, Jason Donald, and Lou Marson. He was beloved in Philadelphia, helping the Phillies return to their second straight World Series, and earning the team’s only two wins against the Yankees that October.
Unfortunately for the Philadelphia faithful, the Phillies turned around and flipped Lee to the Mariners the following offseason. Lee’s heart remained in Philly though, and Phillies fans wanted to see him back in red pinstripes too. The reunion was realized fairly quickly when Lee rejoined the Phillies for the 2011 season through free agency, as part of a dominant pitching staff that included Roy Halladay, Roy Oswalt, and Cole Hamels.
Despite having one of the all-time best rotations, the Phils were unable to make it back to the World Series, with their bats failing to provide much pop after Game One of the NLDS against the Cardinals.
Lee was sidelined mid-season in 2014 due to injury, and never pitched again. He compiled a WAR over 20 from 2011-2014 in his second go-round with the Phils, though the team didn’t make it back to the playoffs after ’11.