Red Sox Roasted With 2 Players on 'Worst MLB Contracts' List

It's no secret that Chaim Bloom's tenure as Chief Baseball Officer of the Boston Red Sox left fans frustrated more often than not. Fortunately, Red Sox owner John Henry came to his senses when he fired Bloom in September before replacing him with Craig Breslow, who hasn't wasted any time attempting to clean up his predecessor's mess.

But even with Bloom in the rearview, some of his past decisions (or lack thereof) could still wind up hurting the Red Sox's future. That's why The Athletic's Cody Stavenhagen has a pair of Boston contracts as two of the worst in all of Major League Baseball ahead of the 2024 campaign.

Red Sox Worst Contracts

Stavenhagen lists Trevor Story (No. 6) and Chris Sale (No. 8) as having two of the worst MLB contracts at the moment. While both men have been effective contributors in the past, injuries have caused their contracts to become albatrosses around the Red Sox's neck.

Trevor Story: $22.5 Million in 2024

Story arrived in Boston in 2022 on a six-year, $140 million contract that made sense at the time. After all, the ex-2011 first-rounder had just finished 12th or better in NL MVP voting in three of the four previous seasons with the Colorado Rockies.

Unfortunately, injuries have plagued Story's tenure in Boston. After being held to just 94 games in 2022 due to a myriad of injuries, the 31-year-old infielder was limited to 43 last season. He didn't do much with the little playing time he saw in 2023, tallying three home runs and 14 RBIs with a career-worst .202/.250/.316 slash line across 158 at-bats.

If Story was a free agent at the end of the season, his contract wouldn't be that bad, but that isn't the case. The Irving, TX native is set to make $22.5 million in each of the next two seasons before jumping up to $25 million in 2026 and 2027. Yes, Story can opt out after 2025, but I highly doubt he'll throw all that money away based on how his career is going.

Chris Sale: $27.5 Million in 2024

It isn't hard to see why Sale's contract is among the MLB's worst, too — even if Bloom didn't hand it out. After beginning his Red Sox tenure with back-to-back Cy Young-quality campaigns, Sale agreed to a five-year, $145 million extension with Boston in March 2019.

It didn't take long for the deal to turn sour, though. Sale missed the entire 2020 campaign due to Tommy John surgery and only pitched 48 1/3 innings between the 2022 and 2023 seasons.

Sale put the injury issues behind him for the most part last season by starting 20 games (his most since 2019), but it quickly became clear that he was no longer one of the baseball's best hurlers. His 6-5 record wasn't all that impressive while his 4.30 ERA was the second-worst mark of his 13-year career.

While there isn't as much time left on his contract compared to Story, Sale is still slated to make $27.5 million in 2024. That's appropriate for his old self, but not today's version. There's also a $20 million club option for 2025 if the 34-year-old 1) finishes 10th or better in AL Cy Young voting and 2) doesn't end the year on the injured list.

At the end of the day, it's clear that Story and Sale have a lot of work to do to live up to their contracts' value. Whether or not they can stay healthy enough to do so remains to be seen.

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