3 contracts the Red Sox will regret this offseason

Baseball numbers are weird, and when it comes to money they're especially bizarre. Without a salary cap, a MLB player's average salary comes second only to the average basketball player on the list of athlete earnings in the United States. Contract numbers that might seem astronomical compared to almost any other occupation in the world, like the MLB minimum $720,000, represent either an untested player or one who's trying to salvage his career. At that rate, it's hard to conceive of any player who is underpaid, though giving a player only a couple million dollars does, bafflingly, qualify as a bargain in MLB.

Here are three contracts the Red Sox will regret this offseason (if they don't already)

When you consider the kind of contracts the Boston Red Sox are doling out, things become even harder to comprehend. The Red Sox were in the top half of league spenders in 2023, with a total payroll of $183 million dollars, and will probably spend even more in 2024. Unfortunately, over a third of it will go to three players who have enormous contracts they haven't been able to live up to on the field.

It feels wise to include a warning here: some may find the following contracts, which amount to over $300 million over the next 1-5 years, physically unsettling.

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.

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.