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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Chris Sale: 5 years, $145,000,000 through 2024

Former Chief Baseball Officer Chaim Bloom said it best when he wondered incredulously who had the 'Chris Sale voodoo doll' and what the Red Sox had to do to retrieve it. Sale's six years in Boston started on a pretty incredible note; in 2017 and 2018, he had an fWAR of 7.6 and 6.2 — incredible numbers, even more so for a pitcher — and pitched 214 1/3 and 158 innings respectively. He was an All-Star and earned Cy Young votes in both seasons.

Problems started to arise in 2018, when he sat for three weeks with shoulder inflammation, and everything's gone downhill since. In 2019, Sale signed a five-year extension for $145 million with vesting options in 2025. Despite his late season injury in 2018, the Red Sox expected him to be their ace. But 2019 through 2020 were riddled with elbow issues, which eventually resulted in Tommy John surgery after the 2020 season was delayed and shortened, and a 60-day IL stint to begin the 2021 season.

Sale also got COVID in 2021, fractured a rib in February 2022, was hit by a line drive and fractured a finger in July (five days after returning to Boston), and broke his wrist in a bike riding incident completely unrelated to baseball. He went onto the 60-day IL again in 2023 with stress in his shoulder blade. From 2019 through 2023, he only pitched 296 2/3 innings, almost 100 fewer than he managed in 2017 and 2018.

Chris Sale voodoo doll is right. The Red Sox still owe him $27.5 million this year after having coughed up a staggering $60 million over 2021 and 2022 for pitching only 48 innings. Maybe 2024 will be better? Maybe someone will be able to track down the voodoo doll and rescue it from the hands of whatever sadistic Yankees fan it's ended up with? The Red Sox and their fans can only hope, but it's hard to tell how much hope Sale is worth now.