1. Carl Crawford
It seemed that whenever the Rays faced off against the Boston Red Sox, Carl Crawford was doing his best to make their lives miserable.
Naturally, when he became a free agent at the end of the 2010 season, the Red Sox opened the vaults to bring him in. He signed a seven year deal worth $142 million to head to Boston, theoretically adding a dynamic element to the lineup that the team had not had in years.
Instead, Crawford was not the same. He had a slow start to his time in Boston, and then battled injuries. While he attempted to come back in 2012, he clearly was not ready. In the end, the Red Sox unloaded him to the Dodgers as part of a salary dump, with Josh Beckett, Adrian Gonzalez, Nick Punto, and a good amount of cash. It did not matter what the Red Sox got back; they were just happy to see him elsewhere.
The Red Sox clearly did not get their money’s worth. Crawford produced a disappointing .260/.292/.419 batting line in 664 plate appearances, hitting 14 homers and 39 doubles while stealing 23 bases. While he was marginally better with the Dodgers, injuries continued to take their toll and prematurely ended his career.
The Boston Red Sox could not figure out how to get Carl Crawford out when he was on the Rays. Turns out that they just needed to sign him to keep him off the bases.