When the Red Sox traded for Garrett Crochet, they knew they’d be giving up a significant amount of young talent. They probably didn’t envision watching those prospects contribute in Chicago while their new ace battles another injury setback less than two years later.
It’s a trade you can’t really fault Chief Baseball Officer Craig Breslow for making. Frontline starters in their prime rarely become available, and the Red Sox had a glaring need atop their rotation. With Crochet available, Breslow pounced on that opportunity.
However, both Crochet and the Red Sox’s 2026 seasons have gone off the rails. Boston is fading fast in the Wild Card race following another loss to the Tampa Bay Rays, and when the left-hander’s return will be is uncertain at this point.
On the other side of the deal, the White Sox’s resurgence has become a major talking point. Chicago boasts one of the top slugging teams in MLB and is riding it into postseason contention. Braden Montgomery just made his MLB debut, which, combined with Crochet’s latest setback, raises the question of which team could come out on the better end of that blockbuster deal.
Revisiting the Garrett Crochet Trade
GettyBALTIMORE, MD – APRIL 25: Garrett Crochet #35 of the Boston Red Sox pitches against the Baltimore Orioles during the first inning at Oriole Park at Camden Yards on April 25, 2026 in Baltimore, Maryland. (Photo by Scott Taetsch/Getty Images)
The deal made sense at the time, given the direction of the two franchises. The White Sox were coming off a 121-loss season and needed to rebuild with talent, while the Red Sox needed to add that missing piece to their starting rotation for a postseason run.
To achieve their goal, the Red Sox paid a premium for two years of control for Garrett Crochet. In that trade, they sent prospects Kyle Teel, Braden Montgomery, and Chase Meidroth to Chicago. All three players have already debuted for the White Sox. Meanwhile, the Red Sox inked Crochet to a six-year extension.
The left-hander was excellent in his first season in Boston, pitching to a 2.59 ERA while leading the American League in strikeouts (255) and innings pitched (205.1). Crochet finished second in the AL Cy Young voting behind the Detroit Tigers‘ Tarik Skubal. The trade also had strong results for the club, as Boston won 89 games and earned a Wild Card berth.
Based on their 2025 results, you can’t blame the Red Sox for swinging that type of trade. But with the players they dealt starting to filter into the major leagues and experiencing some success, the perception of the trade can shift.
Garrett Crochet Trade Perception Shifts Towards White Sox in Year 2
GettyCHICAGO, ILLINOIS – JUNE 09: Braden Montgomery #24 of the Chicago White Sox celebrates his walk-off, two-run home run in the 10th inning against the Atlanta Braves in his MLB debut at Rate Field on June 09, 2026 in Chicago, Illinois. (Photo by Jayden Mack/Getty Images)
The Red Sox shouldn’t regret making the trade. But injuries have a way of changing how blockbuster deals are viewed, especially when the players sent away begin contributing at the major league level.
Crochet already had Tommy John surgery when he was with the White Sox, and this lat strain marks the second major arm-related injury of his career. For the Red Sox to come out winners of this deal, they need Crochet to be an ace over the duration of his contract.
But in the sense of where the two clubs are headed in 2026, it does add the possibility that the White Sox can win their end of the deal. Teel, Meidroth, and Montgomery are expected to be lineup regulars for the foreseeable future, as their contention window just opened. Chicago is 35-31 on the season and looking at potentially their first playoff berth since 2020.
It’s still possible for both teams to achieve their win conditions from the trade. The Red Sox still have enviable starting pitching depth, even with Brayan Bello’s struggles. The White Sox have an exciting young core of hitters.
It’s still too early to declare a winner of the Garrett Crochet trade. The Red Sox got the ace they wanted and a postseason appearance in return. The White Sox have already made room for Teel, Meidroth, and Montgomery into what they hope is their next contender.
But with Crochet injured and Chicago’s young core beginning to emerge, the trade looks far more balanced today than it did a year ago.
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