1. Chris Sale – 3 Years, $85 Million Remaining
It makes total sense why the Red Sox paid Chris Sale after they won the 2018 World Series, rewarding him with a five-year, $145 million deal in March 2019 that was set to take effect in 2020. That’s a relative bargain for one of the game’s elite swing-and-miss artists, and also the Red Sox are the RED SOX.
Or, at least they were under Dave Dombrowski. Back then, men used to be men.
Sale, naturally, succumbed to the elbow injury most had long predicted for him based on his violent windup in the summer of 2019, ending that season — his worst in the bigs — with a 6-11 record and 4.40 ERA (despite 218 strikeouts in 147.1 innings).
When the 33-year-old Sale is at his best, he’s still nigh unhittable. Unfortunately, the 33-year-old Sale is currently on the IL yet again with a rib fracture, his timetable for return still unclear. The 33-year-old Sale is also 33 years old.
Since inking his mega-deal, the left-hander has rarely been available, and came back at the tail end of 2021 to provide a playoff boost … but often looked like an imitation of his best self instead. Boston worked Sale back into shape with “warmup” regular season outings against the Orioles and the AL’s dregs, but the Astros took him to the woodshed early in the ALCS, then edged past him in his second outing of the series.
We’re still waiting for a 2022 encore. If Sale looks excellent, he can opt out at the end of the campaign. If he doesn’t, he’ll still be on Boston’s books through 2024 — or 2025 at an additional $20 million if his option vests with a standout ’24 campaign.