The Boston Red Sox's hunt for a No. 2 starter continues in earnest this offseason, as the team experienced a significant drop-off in quality behind Garrett Crochet.
A role that was originally slated for Tanner Houck and was, at times, admirably filled by Brayan Bello in 2025, still needs its leading man, and odds are that the Red Sox will seek their answer via trade yet again. They're already entangled in rumors for Hunter Greene, and Milwaukee Brewers ace Freddy Peralta would offer a seamless right-handed compliment to Crochet.
However, the true prize of the offseason is Tarik Skubal of the Detroit Tigers, the soon-to-be two-time reigning American League Cy Young Award winner. He and Crochet will undoubtedly finish first and second for the top pitching award, and the opportunity to pair them together could give Boston the best 1-2 punch it has had in the rotation since Pedro Martinez and Curt Schilling helped break the Curse of the Bambino in 2004.
Bleacher Report writer Tim Kelly agrees with that sentiment, placing the Red Sox as the second-best suitor for Skubal this winter, behind only the New York Mets.
A Tarik Skubal trade is perfect for the Red Sox... besides the price
It's sort of funny that the whole conversation around the Red Sox's rotation is that they need a sidekick for Crochet, and yet the new man of interest is the only AL pitcher who is better than him, but Craig Breslow might as well aim for the moon while he can. The Red Sox are a young team with most of their core locked into long-term extensions. There's room to add one of the best pitchers in baseball to this roster (obviously), but the ramifications of adding Skubal will be severe.
For one thing, he'll deplete the prospect depth that Boston has been hoarding to some degree, though perhaps not as much as someone like Greene would. He is a rental starter, and that lack of team control for pitcher nearing 30 years old will absolutely dampen the shock of the acquisition cost.
The more pressing issue is that, as a rental, Skubal is in need of a hefty new contract. The reason he's even rumored to be available is a purported $250 million gap in negotiations with the Tigers, which you can safely assume means Skubal has every intention of blowing past Yoshinobu Yamamoto's current record of $325 million for a pitcher.
The Red Sox can afford that — Alex Bregman's $40 million is coming off the books after his decision to opt out and could be allocated directly to Skubal's new deal — but it'd basically lock the franchise in financially. Don't forget, Crochet, Kristian Campbell, and Roman Anthony all signed extensions this year that start kicking in during the 2026 season; a new Skubal contract would almost certainly push the Sox beyond the first threshold of the luxury tax.
None of that's to say the front office should hesitate if they get a chance to bring Skubal in to town. From Eckersley-Tiant in 1978 to Clemens-Hurst in 1986 to Martinez-Schilling in 2004, Boston has a long history of elite pairs of starters. Crochet-Skubal could be next in that impressive lineage.