The Detroit Tigers have an impossible decision to make with likely AL Cy Young winner Tarik Skubal this winter. Should they keep Skubal and risk losing him for nothing in free agency next offseason, or trade one of the best pitchers in Tigers history and alienate a fanbase hungry for their first World Series victory since 1984? The Cubs – and many teams that would be interested in Skubal – can help provide an answer. What could very well determine if the Tigers trade Skubal is what teams are willing to offer in return.
Skubal could have plenty of interested suitors because he is the best pitcher on the planet. If any team is familiar with the risk that comes with acquiring a player in a contract year, it's the Cubs, who are about to lose out on Kyle Tucker in free agency. Chicago traded top-100 prospect Cam Smith and more for one season of Tucker, and though the 2025 season did lead to a postseason appearance, fans in the Windy City are left wondering what if.
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Why the Chicago Cubs are a match for Tarik Skubal
The Cubs rotation was a bit of a patchwork mess at times this season, thanks in part to an injury to ace Justin Steele. However, pitchers like Shota Imanaga, Matthew Boyd and Cade Horton stepped up when they had to – namely the postseason – and the Cubs won the Wild Card series over the San Diego Padres. Unfortunately for Chicago, Imanaga has a chance to opt out of his contract in a few days' time, and could make their rotation dilemma quite urgent. Innings-eaters like Colin Rea and Aaron Civale are also set to test the market.
There's little denying the Cubs will be in the market for rotation help this offseason. The question is just how much, and whether they'll try to land a big fish in a small pond. The free-agent market doesn't offer many intriguing top-of-the-rotation options for the Cubs, though Dylan Cease has been connected to Chicago already.
If Jed Hoyer were interested in another trade for a rental, Skubal would be a natural fit and instantly transform Chicago into a World Series frontrunner, even without Tucker. As intriguing as acquiring Skubal would be, the Tigers asking price is quite high. In return for Skubal, Detroit would want impactful, young players who could contribute to their team right now. Per Jim Callis of MLB Pipeline, that deal would start with Horton and Matt Shaw.
If that seems like a lot for a rental, that's because it is. The Tigers have set the asking price so high that any team actually willing to meet it would force Scott Harris's hand. While reports suggest the Tigers and Skubal are nine figures apart on a potential deal, that doesn't make it impossible. Much of that amount is likely due to the years Skubal and Scott Boras want vs how many the Tigers offered in the first place, so the number isn't as scary as it looks.
Needless to say, if the Tigers are going to trade one of the best pitchers of his generation, it'll be for a haul of young talent in return.
Why the Cubs shouldn't trade for Tarik Skubal at his current asking price
If the Cubs were to trade for Skubal, they ought to wait until closer to spring training or even at the deadline in July, when the Tigers would be more desperate to get something for his services. Right now, Detroit is sitting pretty with all the negotiating power. The Tigers just made a postseason appearance and came a game away from the ALCS. Skubal will win his second-straight AL Cy Young, and the sides have barely even discussed an extension. Once Harris sits across the table from Boras, however, that could change in a heartbeat.
The Cubs are not one player away from winning the World Series. By trading that much young talent for a player of Skubal's caliber, they'd essentially be going all-in on 2026 (much like the Tigers' current dilemma). Chicago hired Craig Counsell in the first place to build through player development and the farm system. Counsell is worth a few wins in his own right, which is why he's the highest-paid manager in baseball. Taking a home run swing on Skubal and abandoning much of what Counsell and Hoyer have built in just a few years together goes against their best interest long term.