2011 saw the Red Sox attempt to put an end to the shuffle in left field by signing an established star in free agency to fill the position, but that plan backfired horrendously when that supposed star turned out to be Carl Crawford.
Crawford spent the first nine years of his career with the division rival Rays, earning four All-Star appearances and doing enough damage against the Red Sox to convince them that the best way to beat him was to entice him to join them. Boston inked Crawford to a 7-year, $142 million deal that they would immediately regret.
You can point to the Crawford deal as an example of the dangers of handing out expensive long-term deals to players on the verge of turning 30, but his personality had as much to do with his decline as any erosion in skills. He never looked comfortable playing in Boston after spending his career in the small-market city of Tampa Bay and wilted under the pressure. Crawford was barely above replacement-level in his first season with the Red Sox, producing 0.1 WAR over 130 games.
Injury sidelined Crawford through a significant portion of the 2012 season. He appeared in only 31 games before he was traded in an epic waiver deal in August. The Red Sox sent Crawford, Adrian Gonzalez, Josh Beckett and Nick Punto to the Dodgers for a package of players that never amounted to anything in Boston, yet was still considered a heist for the Red Sox. The trade discarded a couple of disgruntled veterans and cleared about a quarter of a million dollars in future salary from the payroll, paving the way for massive roster renovations the following winter that resulted in a revamped Red Sox team that would go on to win the 2013 World Series.
Next: Championship Year