Chris Sale reveals his top regret from his time with Red Sox
"That’s just one of the bigger regrets in my life. It’ll always be."
On paper, Chris Sale accomplished plenty during his seven seasons with the Red Sox.
The southpaw finished second in the AL Cy Young Award voting and ninth in AL MVP voting during his first season with Boston in 2017, going 17-8 with a 2.90 ERA and a whopping 308 strikeouts in 214.1 innings of work.
The following year, he helped a dominant 2018 roster win a World Series — posting a 2.11 ERA over 27 starts before striking out Manny Machado for the final out of Boston’s title run.
But those impressive early returns gave way to disaster, especially after signing a five-year, $145 million extension with the team in March 2019.
Speaking to ESPN’s Jeff Passan this week, Sale said that his inability to deliver after putting pen to paper on that hefty new contract still haunts him.
“It’s a double-edged sword for me,” Sale, who now pitches for the Braves, said. “The whole reason I got traded (to Boston) was to help them win a World Series. And I feel satisfied in doing that. It’s just obviously what happened after that.
“That’s just one of the bigger regrets in my life. It’ll always be. They made a commitment to me, and I didn’t live up for that. We made a deal: ‘We’re going to give you this because you’ve done this and you’re going to continue to do that.’ Well, I didn’t hold up my end.”
After Sale signed that extension, he only logged 298.1 innings from 2019-23. He missed the entire 2020 season due to Tommy John surgery while missing extended time on several other occasions due to freak injuries.
In just his second start of the 2022 season, Sale fractured his pinky finger after getting struck by a line drive by Yankees outfielder Aaron Hicks. Boston expected Sale to return later that season, but he was ruled out for the rest of the year just weeks later after fracturing his wrist during a bicycle accident.
The Red Sox eventually traded Sale to Atlanta back in December, with the 34-year-old lefty signing a two-year, $38 million extension with Atlanta shortly after.
In a cruel twist of fate for the Red Sox, the player they acquired in that deal — Vaughn Grissom — is expected to miss the start of the regular season due to a groin strain.
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