The Boston Red Sox could form one of MLB's premier starting pitcher tandems if they acquire Tarik Skubal to pair with Garrett Crochet. While no official reports confirm Skubal's availability, some analysts speculate he may be traded this offseason. The Red Sox's well-known need for a top-tier arm could be addressed by obtaining the pitcher who currently rivals Crochet in the Cy Young race.
Skubal, the (likely) future two-time AL Cy Young Award winner, is headed into the final year of arbitration. The soon-to-be 29-year-old is in the midst of one of the most dominant stretches on the mound in baseball history, and due to some injuries early in his career, will have less than 1000 innings by the time he is set to reach free agency. MLB experts believe he will be the highest-paid pitcher in baseball if he hits the open market.
Detroit has the opportunity to give him the extension and make him a life-long Tiger, but insiders believe it doesn't have the financial capital to make that happen. Reports suggest extension talks between the two sides haven’t started yet. The Tigers would be foolish to let Skubal play out this season in Detroit without an extension, knowing they won’t be able to re-sign him, and allowing him to leave for nothing the next offseason. If they won’t re-sign him, then the only other option is a trade.
The Red Sox are going to be one of the very few teams that will have the ability to make the trade for the lefty this offseason. Not only do they have the pieces necessary to make the trade, they also have the financial capabilities to extend him. Ultimately, that will be the biggest factor in determining who may acquire him.
Two things I believe to be true
— Jim Costa (@JimCosta_) October 14, 2025
1. Scott Boras and Tarik Skubal want to hit free agency a year from now. No extension this offseason
2. The Tigers are not going all in to win with Skubal in 2026
There is only 1 conclusion: You trade him at the winter meetings#RepDetroit
If the Red Sox want to trade for Tarik Skubal, they better have a big check ready
This situation is similar to Francisco Lindor’s. He was traded from Cleveland to the Mets at the same point in his career that Skubal is now. The Mets didn’t have a contract already agreed upon, but knew that they were going to get one done to make the trade worthwhile. The opposite happened to the Yankees after the Juan Soto trade — they hoped to be able to extend the superstar after their 2025 World Series loss, but the Mets swooped in and offered him a bigger deal.
Trading for the reigning Cy Young winner will cost major prospect capital. He is in the running for the best pitcher in baseball right now (with Paul Skenes), but no one will give up that capital without the guarantee of an extension with him.
If the Red Sox even want to sniff at trading for Skubal, John Henry better be ready with a blank check. The Fenway Sports Group has the money to make it happen. It just committed $40 million a year to Alex Bregman (he has since opted out, however) while it had Rafael Devers under contract for $28 million a year, and Trevor Story making $25 million. This organization is by no means struggling for money.
Craig Breslow is no fool. He knows what it would take to make that trade, however uncomfortably astronomical the return would be, but he would need Henry’s assurance that the club would do whatever it takes to keep Skubal around for the long haul.