The New York Yankees and Detroit Tigers both started their offseason after the divisional round of the Major League Baseball playoffs. In many ways, both teams mirror each other when it comes to how their seasons went. They may cross paths again if Brian Cashman decides to call Detroit about Tarik Skubal. Any move concerning the pitcher will involve at least Spencer Jones.
Cashman spoke about the chance that Jones plays for New York in 2026. While explaining the process, the general manager harped on the fact that a lot of the decision-making depends on what happens this winter. The Yankees are under pressure to make moves to bolster the roster before what could be a make-or-break season in 2026. Those improvements require sacrifice.
For as long as he goes without a contract extension from the Tigers, Skubal is the best player in the 2027 free agency class. Detroit has not said much about extending the American League Cy Young Award winner on a long-term deal. The Tigers are a small market team who can ill afford to sink a large amount of money in anyone, regardless of how talented they are.
Skubal broke records both in the postseason and throughout his 2025 campaign. Outside of Paul Skenes and a great season from Garrett Crochet, there is no question that he is the best pitcher in MLB. If he becomes available at any point in the next 12 months, teams around the league will line up with offers to try and poach the ace.
If the Tigers want to keep Skubal, they need to extend him soon. Here is what they could get from the Yankees in a trade if they don't.
Tigers receive: OF Spencer Jones, SP Will Warren, SP Luis Gil
Yankees receive: SP Tarik Skubal
Why should the Tigers trade Skubal away?

Skubal has been nothing but dominant for the past two seasons. The Tigers ace was an X-factor for his team heading into the playoffs. While Detroit went home in the ALDS, the loss was not on Skubal. He was excellent, sporting a 1.74 ERA across 20.2 innings pitched across three starts. The All-Star starter also had 36 K's, one of the most efficient marks in postseason history.
Unfortunately for Detroit, the team plays in a small market. That means that the front office does not have as much money as New York or Los Angeles does to keep its players happy. At a certain point, the Tigers need to figure out whether or not Skubal is worth the money it will take to retain him. As sad as it is, Skubal spending his whole career in Detroit is simply unreasonable.
The Tigers would have their pick of trade packages if they put their ace on the trade block. The Yankees have plenty of young talent to offer for any star that becomes available. This deal makes the most sense because of the optics around all three players. Jones has yet to play in the major leagues. Both Warren and Gil struggled down the stretch of the 2025 regular season.
Detroit would get a discount on all three young stars in a Skubal trade. Sending its star away is a big risk, and the front office needs to ensure it gets as much as possible in return. That offer is the best that the Tigers are going to get.
Why should the Yankees trade for Skubal?

Cashman's job has come into question after the Yankees fell short of expectations yet again this fall. He and New York manager Aaron Boone are under the microscope, and their decisions this offseason could determine their future. Cashman, for one, has his work cut out for him when it comes to adding another star to the starting rotation. Luckily for him, Skubal is a perfect fit.
Detroit's No. 1 starter is the favorite to win the 2025 AL Cy Young Award. He would be the ace of almost any pitching staff in the league. Except the Yankees'. He and Gerrit Cole would form the league's best one-two punch on the mound and dominate the competition if they stay healthy. It would cost the Yankees their future, but it is a deal they cannot pass up on this offseason.
New York will be a contender for as long as Judge is elite. The Yankees captain defeated some playoff demons this year, but there is no telling how much longer he will be great. Cashman needs to make the most of the open championship window and bring in as many stars as possible. Skubal's expiring contract makes him an easy target, whether it is for just one year or the next ten.