Background:
Trading for Chris Sale entering the 2017 season was one of Dave Dombrowski's "get us over the hump" moves that ultimately did in fact get the Sox over the hump. (The other moves being signing David Price, trading for Craig Kimbrel, and then signing JD Martinez). While Yoan Moncada and Michael Kopech were tough to part with, Boston fans can live with the results of the trade no matter how their careers pan out. The team won the World Series and Sale was a big reason why. Just like with the Hanley Ramirez/Josh Beckett/Mike Lowell swap from back in the day, winning is all that matters.
Sale's first season and a half in a Red Sox uniform was utterly electric. The organization finally found a starter with the ace mentality that was missing ever since the bungled Jon Lester extension conversations. I mean, in his first start with the Sox on a frigid April night, Sale wasn't wearing anything under his jersey. The cold weather didn't phase him. He just wanted to compete and win - a perfect fit with his new city.
His first campaign with the Red Sox was his best, as Sale struck out a whopping 308 batters in 214 1/3 innings, winning 17 games and registering a 2.90 ERA. He finished second in the American League Cy Young voting before finishing in fourth the following year.
Yet as promising as things started out, the elbow issues that analysts predicted would happen to Sale finally arrived. The southpaw finally underwent Tommy John surgery last spring.
2020:
As much as Sale getting hurt sucks, there really was never a better season for it to happen. Not only were the Red Sox awful in 2020, but the shortened season meant that he was able to begin rehab without missing actual games. By all reports things have gone pretty smoothly, minus some neck stiffness around the holidays. Of course, it's far better for him to have suffered a setback due to a neck issue than any lingering elbow pain.
Contract Situation:
Oy. Set to become a free agent after 2019, Dombrowski signed Sale to a five-year, $145 million extension before the season started. He most certainly earned this contract, but the timing of the deal was brutal as his injury issues immediately worsened, leading to the surgery last year. There's no doubt that the Sale extension plus Nathan Eovaldi's contract led the franchise on a path to the Mookie Betts trade, but that's a topic for another day. Set to turn 32 in March, Sale is under contract through 2024.
2021 And Beyond:
Currently, Sale is technically on the 60-day IL and the Sox don't expect him back until late-May or early-June. We really won't have an exact idea until we get closer, and by all reports the team is going to play things extra cautiously with him. Expectations should be tempered early on with an eye on him returning to SP1 status to begin '22.
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