5 worst contracts in Boston Red Sox history

Mar 9, 2020; North Port, Florida, USA; Boston Red Sox outfielder Rusney Castillo (38) works out prior to the game against the Atlanta Braves at CoolToday Park. Mandatory Credit: Kim Klement-USA TODAY Sports
Mar 9, 2020; North Port, Florida, USA; Boston Red Sox outfielder Rusney Castillo (38) works out prior to the game against the Atlanta Braves at CoolToday Park. Mandatory Credit: Kim Klement-USA TODAY Sports /
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(Photo by Adam Glanzman/Getty Images)
(Photo by Adam Glanzman/Getty Images) /

2. Pablo Sandoval

It is sad that the most memorable moment of Pablo Sandoval‘s tenure with the Boston Red Sox is more memorable for a comedic moment than any production he would have had.

That moment came when Sandoval’s belt broke during a plate appearance. He had already received a great deal of derision for his lack of conditioning, although round is a shape. While he was able to appear in 126 largely forgettable games in 2015, that was the highlight of his time in Boston.

Injuries left Sandoval to appear in 35 more games with the Red Sox before he was released. Sandoval ended up returning to the Giants where he turned his career around and once again became a useful part of the lineup.

That was not the case at all with the Red Sox. His signing had seemed questionable at the time, a way to sell panda heads to casual fans, and his performance did nothing to dispel that thought. He produced a .237/.286/.360 batting line in 620 plate appearances, hitting 14 homers and 27 doubles. In exchange for a five year deal worth $95 million, the Red Sox received approximately a year’s worth of playing time.

Pablo Sandoval was a questionable fit with the Boston Red Sox from the beginning. Yet somehow, his was not the worst contract the team had handed out.