Chris Sale's Massive Contract Extension Looks Impossibly Bad Four Years Later

After the Boston Red Sox ripped through all of Major League Baseball to win the 2018 World Series, the front office doled out quite a bit of money. A large chunk 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 a fully guaranteed five-year, $145 million extension that kicked in 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 delivered, thus he was rewarded.

Four years later, the decision looks worse than anyone could've possibly imagined.

The entire Red Sox franchise came crashing back down to Earth in 2019, including Sale. He posted a 6-11 record with a 4.40 ERA. It was a down year, which happens. If Boston hadn't forked over all that cash before the year, they could've re-evaluated Sale's future with the franchise because he would have hit free agency after the year. Instead, for better or worse, they were stuck with him for another five seasons. And it has been for worse. Not because Sale has lost his stuff, but because he can't get on the field.

Since Sale's new contract began in 2020, he's pitched a whopping 47.4 innings. Total. He didn't get on the field in 2020 while recovering from Tommy John surgery. It took him until August 2021 to return. He was decent in the last month and a half of the year, going 5-1, but struggled in the postseason by allowing 10 runs in three starts.

A reasonable person would get that it's tough to leap from Tommy John rehab to elite pitching right away, so expectations were high for 2022. But it took all of two months for things to start going sideways. Sale fractured his rib in February while pitching batting practice that kept him out for a whopping five months. He made his first start of the year on July 12 and struggled in a three-inning outing before taking the mound again on July 17 and managed to earn all of two outs before taking a liner to the finger and exiting the game immediately. He underwent surgery soon after and there was hope he'd be able to return at some point this season.

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

Sale is really taking the idea of "snake-bitten" to a whole new level here. An absurd sequence of events dating back to 2020.

Sale will receive $30 million this year for less than five innings of work. The Sox are on the hook for $75 million over the next three years. It is, in many ways, the absolute worst-case scenario. If Sale was pitching and was bad, that's one thing. But he hasn't even managed to put together more than two months' worth of work in three years. It's hard to see this working out well for Boston and Sale's contract has rocketed up the power rankings as far as worst MLB contracts go.