Perhaps the most important assignment this offseason for Boston Red Sox chief baseball officer Craig Breslow is to acquire a proven No. 2 starting pitcher.
With Garrett Crochet at the top of Boston’s rotation, the Red Sox have a top-five starting pitcher and a few promising young starters around him. What if, rather than a No. 2, Breslow got wild and went after another ace to pair with Crochet? Yes, Tarik Skubal-Red Sox buzz has already begun, and it’s only getting louder.
An October 29 article from The New York Post’s Jon Heyman doubled down on prior reports that Skubal and the Tigers appear to be headed in different directions, as the two sides have never seen eye-to-eye on contract extension numbers.
Skubal is thus considered a viable trade candidate right now, and the Red Sox keep getting linked to the lefty.
Jim Bowden suggests the Red Sox could trade for Tarik Skubal
The original offer the Tigers made to Tarik Skubal was lower then $80 million for 4 year per @JonHeyman
— Matthew Crory (@matthewcrory) October 30, 2025
This would leave the two sides facing a gap more than $320 million dollars apart.
Further increasing the likelihood of a trade this offseason heading into his final year. pic.twitter.com/QDB5cA4DKG
The most recent insider talking Skubal-Sox was Jim Bowden of The Athletic. Bowden identified Boston’s two biggest needs this offseason to be a starting pitcher and a corner infielder, and Bowden noted something interesting about the Red Sox’s preferred means of acquiring the former.
“The Red Sox are focused on adding starting pitching, and they have plenty of prospects in their strong farm system to perhaps trade for top arms like Tarik Skubal, Hunter Greene or Freddy Peralta,” Bowden said (subscription required). “They also have the financial freedom to land one of the top starters in free agency, though trading for a top-tier starter is their preferred route.”
If Bowden’s intel is accurate, Breslow would presumably be exhausting pathways to acquire a Skubal or a Peralta (or another starter available for trade) before going all-in on free-agent arms like Dylan Cease or the newly available Shota Imanaga.
With all due respect to Greene and Peralta, Bowden’s mention of Skubal in all of this is what has some Red Sox fans wide-eyed and starting to believe that Breslow can pull off the deal of the offseason.
Dear @Buster_ESPN,
— Tyler Milliken (@tylermilliken_) November 5, 2025
Please don’t tease me with the Red Sox and Tarik Skubal in the same sentence. pic.twitter.com/dyA7kgErth
Of course, winning a bidding war for Skubal against other, high-spending suitors wouldn’t be easy (the New York Mets have emerged as a rumored landing spot). Also, acquiring Skubal would likely be a one-year rental situation followed by another bidding war next offseason. Boston is experiencing a similar dynamic right now with Alex Bregman’s free agency (Bregman and Skubal are both represented by Scott Boras).
But even for one year of Skubal, wouldn’t the juice be absolutely worth the squeeze? A healthy Skubal and a healthy Crochet in the same rotation for a playoff series would make Boston one of MLB’s most terrifying contenders, regardless of how the rest of the roster shakes out.
Here's the catch. Some fans are already suggesting that Boston wouldn't be able to land Skubal without giving up Roman Anthony. For now, let's save that a discussion for another day.
