New Brave Chris Sale Reveals ‘Big Regret’ From Red Sox Tenure

Chris Sale helped the Red Sox reach baseball’s mountaintop in 2018, but not much went right in Boston for the left-hander after hoisting the Commissioner’s Trophy.

Five months after Sale sealed Boston’s fourth championship in 15 years, the club rewarded the southpaw with a five-year, $145 million contract extension. It proved not to be a shrewd move for the Red Sox, as Sale dealt with a slew of injuries and only made 56 starts from 2019 through last season.

Boston ultimately said goodbye to Sale via trade in late December, and he has a great opportunity in front of him with the Atlanta Braves. Still, Sale feels great remorse about how things ended with his former team.

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“It’s a double-edged sword for me,” Sale told ESPN’s Jeff Passan. “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.”

Sale offered similar remarks before his first spring training with the Braves. The seven-time All-Star doesn’t view his Red Sox tenure as a success — despite the World Series ring — as he only was fully healthy for one of his seven seasons with the franchise.

Yes, Boston should have received a lot more from the veteran starter while he called Fenway Park home. But as you can tell from Sale’s comments, the missed time wasn’t due to a lack of passion and desire to win.