The Boston Red Sox have recently become famous for their former players, whether they were traded or left in free agency, thriving with their new teams. Kyle Harrison is the latest example after the Milwaukee Brewers brought the best out of him. Outfield prospect James Tibbs III is still balling out in the Los Angeles Dodgers organization, although he's cooled down a a bit since hitting 11 homers between March and April.
But the original crushing trade (at least, since Craig Breslow took over as chief baseball officer) is the one that sent Chris Sale to the Atlanta Braves in exchange for young infielder Vaughn Grissom in December 2023. Sale reminded Red Sox fans how incredible he still is when he came to Boston on May 28.
Sale pitched five, six-hit, two-run innings on his old mound. He fanned eight Red Sox and walked three. His fastball velocity was 1.5 miles per hour above his season average, which has steadily increased each year removed from his last year in Boston.
Sale has a 2.01 ERA this season (seventh-best in MLB, a 0.94 WHIP (fifth-best), 80 strikeouts (sixth-best) and 17 walks over 67 innings. In his age-37 season, Sale is keeping pace with some of the best pitchers in the league this year, such as Paul Skenes, Cam Schlittler and Dylan Cease.
Another dominant outing by Chris Sale against Red Sox reminds fans of horrible trade
I’ll never understand Chris Sale magically gaining back 5 mph as soon as he joined the Braves in his age-35 season
— Daniel Fox (@DanBFox1287) May 28, 2026
The worst part of the 2023 trade might be that the Red Sox retained Sale's entire salary for what ended up being the best season of his career. The lefty and, at that point, 14-year veteran, netted his first ever Cy Young Award and pitching Triple Crown with a 2.38 ERA, 2.09 FIP and 11.4 strikeouts per nine innings over 177.2 frames. Meanwhile, the Red Sox's ace that season was Tanner Houck, and that only lasted a few months.
The Red Sox don't necessarily need Sale to have a successful rotation — Sox pitchers have a 3.25 ERA in the last month, eighth-best in the league and one point above the Braves — and he only had one year left on his contract when Boston shipped him to Atlanta. There's no promise that he would've returned to the Red Sox as a free agent, but it seems most likely that he wouldn't. Not only would Boston probably not have approached him about another contract due to his long injury history, it wouldn't have offered a two-year, $38 million contract to a 35-year-old through his age-37 season because it's concerned about signing players over a certain age.
The Sale trade was a well-established disaster for Boston even before the pitcher won his first Cy Young, and certainly well before he started owning the Red Sox with his new team. Many Sox fans were glad to see the chronically-injured Sale go at the time, but precious few of Breslow's trades have aged as poorly as this one.
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