4. Chris Sale
Much like the Berrios contract, I thought the Chris Sale contract was a great deal for Boston. They signed him right after winning a World Series and he was one of the better pitchers in the game at that point.
While I liked both at the time, the reasons I don’t like either now are entirely different. Berrios is underperforming his contract strictly because of his performance on the field. Sale isn’t living up to his because he cannot stay on the field.
In the first year under his new deal, 2019, he made 25 starts but pitched to a 4.40 ERA despite posting a ridiculous 13.3 K/9. Since then, Sale missed the entire 2020 season, made just nine starts in 2021, and two starts this season before being shut down again.
Sale has gotten incredibly unlucky with the injuries this season. In Spring Training, he suffered a right rib stress fracture that knocked him out for the first three months of the season. He then returned on July 12th and pitched five scoreless innings against Tampa Bay. But in his second start, he was hit by a come-backer and fractured his pinky finger on his pitching hand.
That injury was going to have him out for a while, and then Sale suffered a fractured wrist in a bike accident, which officially ended his season.
Sale has an opt-out after this season which he almost certainly will not exercise. This means Boston is on the hook for another two seasons at $27.5 million dollars annually for a guy they have no idea whether can stay healthy at all. This money, much like Story’s contract, might be why Boston lets one or both of Bogaerts and Devers leave in free agency or via trade.