When the Boston Red Sox acquired Garrett Crochet from the Chicago White Sox in December of 2024, it felt like a tale of two teams heading in very different directions. Boston had a generational crop of homegrown talent banging down to the door, headlined by Roman Anthony, Marcelo Mayer and Kristian Campbell, with Crochet as the final piece of a potential championship puzzle. As for Chicago ... well, they'd lost 100-plus games for two years in a row, and it didn't seem like that streak would end any time soon. If you were forced to bet on which team would be the first to win a playoff series, you would've put your life's savings on the Red Sox.
Turns out we all would've lost a whole bunch of money. Boston is headed home after the Wild Card Round for the second straight year, and this elimination was even more humiliating than the last. The White Sox, meanwhile, are still very much alive, sweeping the Houston Astros on the road to punch their ticket to the ALDS this weekend.
Pretty much everything we thought we knew about these teams has been flipped on its head over the last two years. How much should that change how we view the Crochet deal in hindsight? FanSided originally had the trade about even, giving the White Sox a B and the Red Sox a B- at the time. Now, though, things look a whole lot different.
White Sox' Garrett Crochet trade regrade
The Crochet return centered around three players: catcher Kyle Teel, outfielder Braden Montgomery and infielder Chase Meidroth. Teel and Montgomery were the headliners, two consensus top-100 prospects that the White Sox hoped would be the foundation for their next competitive window.
Instead, Meidroth might be the biggest win of all. He might not have the most upside, but with his contact skills and slick glove at second base, he's got an awfully high floor that should make him a big-league regular for a very long time. Meidroth posted a 115 OPS+ and 4.5 bWAR in his sophomore season, one of the biggest reasons why the White Sox are where they are right now.
But he's far from the only building block Chicago was able to acquire. Teel has had a hard time staying healthy since the trade, but when he's been on the field he's looked the part of a legit two-way catcher, solid behind the plate with elite barrel and walk rates as a hitter. If he can just avoid injury for a full season, there's no reason he can't become a top 10-15 catcher in the sport — at a minimum.
Montgomery is admittedly a bit behind the other two, a good athlete who needs to figure out how to either make more contact or pull the ball in the air more if he's going to pan out as a Major League hitter. Still: All signs point to both Meidroth and Teel becoming mainstays in Chicago's lineup for years to come, and that's a home run given the question marks around Crochet at the time — question marks that are still swirling despite the success he's had in Boston.
White Sox regrade: A
Red Sox' Garrett Crochet trade regrade
It's pretty ironic that, given the roller-coaster ride Crochet's been on across two years with the Red Sox, Boston's grade in this trade winds up pretty much right where it started.
At the time, we thought that Crochet was a high-risk, high-reward proposition, a lefty with obvious ace stuff who was dogged by workload an injury concerns. Sure enough, we've seen both sides of that coin play out so far: Crochet was one of the very best pitchers in the sport in 2025, finishing second to Tarik Skubal in AL Cy Young voting, but he managed just 30 innings of a 6.30 ERA this year before landing on the IL with a shoulder issue.
Crochet did manage to get back on the field in October, making a relief appearance in Boston's Game 2 loss on Wednesday night. And he could well have a healthy offseason and get back to making good on the six-year, $170 million extension the Red Sox gave him last March. But the fact is that he's cracked 100 innings in a season exactly twice in his baseball career; he's only cleared 150 innings once, and the very next year his shoulder started barking. Can he be a year-in, year-out ace? That remains to be seen, and that means the jury is very much still out for Boston here — especially as they struggle to find upgrades at the exact positions where Meidroth and Teel are thriving.
Red Sox regrade: B-
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