#14 - Trading away Coco Crisp
The Cardinals drafted Coco Crisp back in the 1999 MLB Draft, but in an effort to make a run in the playoffs in 2002, they sent Crisp to the Cleveland Indians along with prospect Luis Garcia for starter Chuck Finley.
Finley was pretty good for the Cardinals, going 7-4 with a 3.80 ERA over 14 starts for the club, but they fell short of championship aspirations and Finley retired after that season.
Crisp, on the other hand, would make his MLB debut later that season, and go on to have a very successful 15-year career for the Indians, Red Sox, Royals, and Athletics. including playing a big role on the World Series-winning Boston team in 2007.
During his career, Crisp slashed .265/.327/.402 with 130 HR, 639 RBI, and 309 SB while playing great defense and even finishing top 15 in MVP voting in 2012. While Crisp was never an All-Star level player, he did make a major impact on multiple winning clubs, and surely was worth more than a half-season rental of a middle-of-rotation, at-best, starter.