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.

“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.”

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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.

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