Chris Sale’s massive contract extension looks incredibly bad after four years


After Boston Red Sox broke through everything Major League Baseball to win the 2018 World Series, the front office spent quite a bit of money. The big part went to Chris Sale, the team’s ace, who went 12-4 with a 2.11 ERA and earned the last out to secure the championship. Boston gave Sale fully guaranteed to a five-year, $145 million extension that began before the 2020 season. At the time, it was seen as the cost of doing business. The Red Sox traded several top prospects for Sale in a classic Dave Dombrowski all-in move, and he followed through, thus earning the award.

Four years later, the solution looks worse than anyone could have imagined.

The entire Red Sox franchise is back on Earth in 2019, including Sale. He posted a 6-11 record with a 4.40 ERA. It was a bad year, which happens. If Boston hadn’t shelled out all that money before the year, they could have reconsidered Sale’s future with the franchise because he would be a free agent after this year. Instead, for better or worse, they stuck with him for five more seasons. And it got worse. Not because Sale lost his stuff, but because he can’t get on the field.

Since Sale’s new contract kicked in in 2020, he has thrown a whopping 47.4 innings. In total. He did not play in 2020 while recovering from Tommy John surgery. It took him until August 2021 to return. He was decent the last month and a half of the year, going 5-1, but struggled in the postseason, allowing 10 runs in three starts.

A reasonable person would understand that it’s difficult to go straight from Tommy John’s rehab to elite pitching, so expectations for 2022 were high. But it took two months for everything to go sideways. Sale broke his rib in February while taking batting practice which kept him out for a whopping five months. He made his first start of the year on July 12 and struggled through a three-inning outing before taking the mound again on July 17 and managing to earn all of two outs before taking a liner on his finger and exiting the game immediately. He underwent surgery shortly after and it was hoped he would be able to return at some point this season.

Today came the kicker. Out of nowhere, the Red Sox announced that Sale had undergone season-ending wrist surgery. How did he hurt his wrist, you ask? He had an accident on his bicycle.

Sale really takes the snakebite idea to a whole new level. An absurd sequence of events begins in 2020.

This year, Sale will earn $30 million in less than five innings of work. The Sox are expecting $75 million over the next three years. In many ways, this is the worst case scenario. When Sale performed and was bad, that’s one thing. But he did not even manage to collect more than two months of work in three years. It’s hard to see that working out well for Boston, and Sale’s contract has skyrocketed up the power rankings as far as MLB’s worst contracts go.

Chris Sale’s massive contract extension looks incredibly bad after four years

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