3 Red Sox contracts we were happy to see end, and 2 we’re still eager to see expire

Boston Red Sox v Toronto Blue Jays
Boston Red Sox v Toronto Blue Jays / Tom Szczerbowski/GettyImages
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1) Red Sox contract we cannot wait to see end: Chris Sale

In the present day, it’s the Chris Sale contract that hurts the most. The good news is he has already helped the team capture the 2017 World Series. The horrific news is he has barely seen the field after 2019.

Sale was acquired in a trade with the Chicago White Sox back in 2016 in a deal that hasn’t hurt the Red Sox all that much. Despite costing Yoan Moncada and Michael Kopech, it’s hard to declare Chicago anything but the loser in the deal.

Sale was not a free agent signing. On March 23, 2019, the Red Sox signed him to an extension. For five years and $145 million, the big lefty ace would stay in town.

It did not take long for the Red Sox to have some regrets. Sale’s 2019 season was pretty bad. At 6-1 with a 4.40 ERA, he was nowhere near the Cy Young contender he had been in every year since 2012.

Unfortunately, things went from bad to worse. Sale underwent Tommy John Surgery which cost him the entire shortened 2020 campaign. He made 9 starts in 2021 and another 2 in 2022. When on the mound, Sale has been effective. It’s also only a small sample size of 11 starts these past three years. 

The contract we’re eagerly awaiting the end of concludes after the 2024 season. Will Sale find redemption before then? At least we’ll always have 2017.