The best left-handed pitcher in the world right now is Detroit Tigers ace Tarik Skubal, who has won two consecutive AL Cy Young Awards.
Skubal is slated to become an unrestricted free agent after the 2026 season. Since he’ll likely get one of the biggest contracts for a pitcher in the sport’s history, very few people expect him to entertain the idea of re-signing with Detroit before hitting free agency to test the open market.
The Tigers are a small-market team and would have a tough time matching what baseball’s biggest spenders could offer Skubal. Therefore, there’s a strong case to be made that the Tigers would be better off trading Skubal this offseason to net a huge return for him, rather than letting him walk in free agency and getting nothing.
Detroit Tigers pitcher Tarik Skubal high-fives teammates in the dugout after a pitching change during the seventh inning at Comerica Park in Detroit on Wednesday, May 14, 2025. | Junfu Han / USA TODAY NETWORK via Imagn Images
The Chicago Cubs pulled off a blockbuster trade for Kyle Tucker (who was in the same contract situation last offseason that Skubal is in right now), which suggests they’d be in play if Detroit were to make Skubal available in a trade.
However, the question is whether Jed Hoyer and the rest of the Cubs’ front office would be willing to part with the pieces it would take to finalize a trade. ESPN MLB insider Jeff Passan alluded to this in a November 18 article by writing, “The Cubs could scrape together enough [in a trade for Skubal], but it would gut their system.”
Cubs Prospect Package To Land Tarik Skubal Could Be Tough Sell
It’s fascinating to consider which prospect the Cubs would need to include in a potential trade for baseball’s best pitcher. Bleacher Report’s Joel Reuter weighed in on this in a November 29 article, with a hypothetical trade package between Detroit and Chicago, writing that the Cubs would need to include the team’s No. 2 overall prospect, Moises Ballesteros, No. 3 overall prospect Jaxon Wiggins, No. 5 overall prospect Kevin Alcántara, and veteran bullpen piece Javier Assad.
Tarik Skubal against the Cubs offense is must-see TV
(@jacobzanolla) pic.twitter.com/H2wKHLxSjV
— Cubs Insider (@realcubsinsider) June 6, 2025
There’s no doubt that Chicago parting ways with three of their five best prospects would be detrimental to their farm system. However, if it resulted in Skubal (even for just one season), the team’s chances of winning a World Series in 2025 would increase drastically. Not to mention that they’d get to keep top prospect, Owen Caissie, in this hypothetical scenario.
But would the Cubs be willing to further diminish their farm system after dealing several top prospects for Kyle Tucker (who is almost sure to sign elsewhere in free agency), if Skubal is likely to do the same next offseason?
Shipping off Ballesteros and Wiggins would leave the Cubs with Caissie as their only Top 100 MLB prospect. Add in Alcantara, and the Cubs would seriously lack the currency to make any future deals. This is all to say that this trade deal would be a very tough sell.
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