The December 2023 trade that sent Chris Sale from the Boston Red Sox to the Atlanta Braves wasn't an easy start to Craig Breslow's tenure as chief baseball officer. Not only did Boston's return player, Vaughn Grissom, miss much of the season with injuries, Sale posted the best season of his career immediately after the deal.
In 2024, Sale earned his first All-Star nomination in six seasons, posted a league-leading 2.38 ERA, 255 strikeouts and other MLB-best metrics in ERA+ (174), FIP (2.09) and strikeouts per nine innings (11.4). He won his first Cy Young Award after earning votes seven other times in his career, including the 2017-18 seasons with the Red Sox. Given that Boston's ace in 2024 was Tanner Houck, it could've justified keeping Sale around for one more year.
Sale had another great season in 2025 (2.58 ERA, 1.066 WHIP) which was unfortunately limited to 125.2 innings after he fractured his ribcage while making a diving play from the mound. He must've decided there's something in the water in Atlanta that he wasn't getting in Boston — on February 24, he signed a one-year, $27 million extension with a $30 million club option for 2027 to potentially play the rest of his career with the Braves.
Former Red Sox ace Chris Sale signs one-year extension with Braves
"He's first-ballot for me..."#MLBNHotStove reacts to the news of Chris Sale's one-year extension with the Atlanta Braves. pic.twitter.com/AjK0LLe7y8
— MLB Network (@MLBNetwork) February 24, 2026
Meanwhile, Grissom's tenure in Boston has been over. Breslow on December 9 flipped him to the Los Angeles Angels in exchange for outfield prospect Isaiah Jackson.
During the 2025 season, Grissom was open about feeling slighted by the Red Sox when he wasn't called up to take Marcelo Mayer's place on the major league roster after he injured his wrist. Breslow decided to give him a change of scenery too soon, a month before the club's whiff on Alex Bregman (the Caleb Durbin, Andruw Monasterio and Anthony Seigler trade now fully eliminates any need for Grissom in Boston, however).
By the time the Red Sox traded Sale to the Braves he only had one year on his contract. Given his pages long injury history and the amount of money he was paid, there was little to no chance of a reunion with Boston, had it kept him around.
Still, it hurts to see Sale thrive with another team, especially because of a bad trade. At least the Red Sox have revamped their rotation to the point that they no longer need Sale, but fans can't help but wonder what his 2024 Cy Young-winning season could've done for that team which was just games away from a playoff berth.