3 contracts the Red Sox will regret this offseason

Boston Red Sox starting pitcher Chris Sale (41)
Boston Red Sox starting pitcher Chris Sale (41) / Eric Canha-USA TODAY Sports
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Trevor Story: 6 years, $140,000,000 through 2028

If any contract could rival Chris Sale's in terms of head-meets-wall levels of frustration, it's probably Trevor Story's. It's hard to say if Story ever deserved the six-year, $140 million contract the Red Sox offered him in 2022. He was a two-time All-Star with the Colorado Rockies, but he was also an incredibly error-prone shortstop whose home run numbers very well could have been inflated by the Coors Effect.

Like Sale, Story's years in Boston have been abbreviated by injury. In 2022, he missed two months from July to August following a hit by pitch to his hand, and went down again in September with a heel injury, resulting in only 94 game appearances. In January 2023, he underwent surgery in his elbow, which kept him off the field until early August.

Though Story's misfortunes haven't been as frequent as Sale's, comparisons are inevitable when they're set to make very similar amounts of money over similar spans of time. Pessimistically, it could also be said that Story just hasn't had enough time with the Red Sox to suffer as many misfortunes as Sale, and maybe he'll disappoint in the same fashion given more time. We can only hope for the opposite, of course, but Story will also be entering his age 31 season in 2024, and aging doesn't exactly make a person less injury prone. When you consider the fact that the Red Sox still owe him almost $100 million dollars, it makes this contract even harder to swallow.