The Chicago Cubs are in the odd position of trying to kick off a youth movement while also still pushing to compete for a championship.
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With an importance placed on clean books and budget flexibility, the Cubs organization has set up a future where young cornerstones are being laid– like Pete Crow-Armstrong, Michael Busch, Cade Horton, and Matt Shaw– while there’s enough available money to pick up whatever remaining pieces are needed to fill out the roster. This is assuming, of course, that the notoriously frugal ownership is willing to spend.
The coming season will be a pivotal one in Chicago’s plans as so much of the core roster is set to become free agents. Possibly gone after 2026 are Seiya Suzuki, Nico Hoerner, Ian Happ, Carson Kelly, Jameson Taillon, Matthew Boyd, and Shota Imanaga.
This future mass exodus underscores the need for the Cubs to establish a base of even more core talent, with years of team control ahead. However, it also underscores the need to go “all in” when it comes to winning this coming season, before the team loses so many mainstay assets.
Bringing in Tarik Skubal
Oct 10, 2025; Seattle, Washington, USA; (Editors note: Alternate crop) Detroit Tigers starting pitcher Tarik Skubal (29) throws against the Seattle Mariners during the third inning during game five of the ALDS round for the 2025 MLB playoffs at T-Mobile Park. Mandatory Credit: Steven Bisig-Imagn Images
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That’s where Tarik Skubal might come in, at least according to some.
Skubal, who presents a case for being the best pitcher in all of baseball, is set to become a free agent at the end of the coming season. His current team, the Detroit Tigers, will not be able to handle the monster payday coming his way and they won’t be able to outbid the suitors pursuing him. That’s why they are reportedly entertaining trade offers for their ace and looking for a haul of talent in return, convinced that they will lose him in free agency and only get back draft pick compensation.
Joel Reuter of Bleacher Report recently tied the Tigers with the Cubs in a Skubal trade proposal that may sound like straight-up fan fiction, but might actually make a bit of sense.
Per Reuter:
“The Cubs have a rotation filled with No. 3/4 starter types and lacking a bona fide ace, and while 2025 rookie Cade Horton has the potential to fill that role, adding a proven frontline starter this winter would make them legitimate title contenders.
After paying a steep price for Kyle Tucker last offseason, only to watch him walk in free agency, they would need to have some belief they would be willing to lock Skubal up with a long-term extension.
If there’s an all-in move to be made for the North Siders, this is it.”
The cost to the Chicago Cubs
Syndication: The Knoxville News Sentinel Knoxville Smokies pitcher Jaxon Wiggins (41) pitches during a minor league baseball game between the Knoxville Smokies and Chattanooga Lookouts at Covenant Health Park in Knoxville, Tenn., on June 3, 2025. © Angelina Alcantar/News Sentinel / USA TODAY NETWORK via Imagn Images
In the proposal, the Cubs get Skubal in return for Chicago’s no. 2 prospect C/DH Moises Ballesteros, their no. 3 prospect RHP Jaxon Wiggins, no. 5 prospect OF Kevin Alcantara, and RHP Javier Assad.
Reuter makes the point that the Tigers, already in a position to compete for a playoff run, would value young, major league-ready talent that could be immediately placed on the field and contribute for years to come. The incoming haul of talent from the Cubs would provide just that, with Wiggins probably being the potential prized jewel of the deal.
Making it make sense
Tigers pitcher Tarik Skubal throws against Mariners during the first inning of ALDS Game 5 at T-Mobile Park in Seattle on Friday, Oct. 10, 2025.
All of this should be prefaced by pointing out that the deal would only make sense if the Cubs were able to lock in an extension on Skubal before the deal was finalized. And, yeah, the Cubs should pay him the monster money he deserves as he comes off off back-to-back Cy Young seasons
The Cubs would be giving up a substantial part of their future by trading away three of their top five prospects and they might be in the very uncomfortable position of having to cough up $30 million+ per season for their incoming ace. But getting a chance to add someone like a prime 29-year-old Skubal as a foundation piece is a once-in-a-lifetime opportunity and the addition would look especially sweet after possibly losing Boyd, Taillon, and Imanaga following next season.
A monster deal like this would be exceedingly difficult to pull off, but it might be worth the price for the Cubs– both in terms of trade capital and money.
Could the Chicago Cubs still be, somewhat, in the Kyle Tucker hunt?
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