Yankees' Garrett Crochet trade package proves why New York let Boston have him

When you're in "win now" mode like the 2025 Yankees, no assets are untouchable. They just have to be utilized properly, or sent in exchange for the correct targets.

In the instance of Garrett Crochet, the White Sox lefty wasn't the ideal option at any price, let alone the one the Yankees were begged to pay. Ultimately, the 25-year-old flamethrower (top-of-the-league starter velocity) landed in Boston on Wednesday in exchange for four players from the Red Sox stacked farm. That package was highlighted by catcher Kyle Teel, one of the Big Four, and outfielder Braden Montgomery, Boston's first-rounder in 2024 who was already threatening to make it a Big Five.

Shortstop Chase Meidroth is also a consensus top-10 Sox prospect, and may start right away in Chicago.

The Yankees were reportedly involved in the bidding during the Winter Meetings, and made the list of five "finalists" for Crochet, but presumably cooled after signing Max Fried to an eight-year deal. Jon Heyman revealed the package the White Sox requested from the Yankees, and while there was no "tax" here, Sox GM Chris Getz intended to gut the Yanks the same way he gutted Boston, asking for Jasson Dominguez and George Lombard Jr. atop the tree. Other than vindictiveness, there was no reason to deplete the farm this way from the Yankees' perspective.

Yankees had no reason to outbid Red Sox for Garrett Crochet after trade package revealed

Why surrender top-shelf young players and eventual extension money when you can sign a chance-of-pace expert with more experience to flesh out your rotation? The Yankees needed a No. 2 or 3. The Red Sox needed to take a chance. The Yankees can afford an expensive Year 7 of regression from Max Fried; the Red Sox couldn't, and had to aim higher.

Crochet will likely dominate in Boston, sure, but now Teel and Montgomery are unavailable for future endeavors. The Red Sox cashed them in for a pitcher with one half-season of ace-level production under his belt, and his breakout year was interrupted by a demand for an extension before throwing potential playoff innings, meaning we've still never seen him under the bright lights. Or the half-brightened lights. Or, honestly, the dim lights. Chicago represented total and complete obscurity. 2025 will represent a challenge unlike any he's ever seen, from the moment the curtain rises.

Last season, when Crochet toed the rubber for his first start of the season, it was also his first MLB start. He whiffed 150 in 107.1 innings in the first half, pitching to a 3.02 ERA in 20 starts. Down the stretch, he threw only 38.2 innings across 12 starts, with the ERA rising to 5.12. Maybe that's where the Chris Sale comparisons should begin.

Made total sense for Boston to roll the dice rather than break the bank for Corbin Burnes. Made no sense for the Yankees to do so, while removing a key piece from their outfield and cashing in a trade chip.

Outbidding the Red Sox using only their financial might for the experienced Fried made perfect sense. Squeezing the top of their weakened farm system to outmaneuver them for Crochet did not.