Cubs face tricky Tarik Skubal trade problem that doesn't bode well for a deal

Apr 18, 2026; Boston, Massachusetts, USA; Detroit Tigers starting pitcher Tarik Skubal (29) pitches during the first inning against the Boston Red Sox at Fenway Park. Mandatory Credit: Bob DeChiara-Imagn Images

The Chicago Cubs are heading towards the 2026 MLB trade deadline as buyers. They are a Wild Card team right now, but not too far back of the Milwaukee Brewers for the NL Central and a first-round bye.

But, with how things stand now, the Cubs' trade deadline is going to be a bit interesting. With a clear need on the pitching staff, with both the rotation and the bullpen, the Cubs could look to someone like Tarik Skubal as a blockbuster addition.

However, ESPN's Jess Passan highlighted how the Cubs are facing a tricky problem when it comes to a Skubal deal this summer. This problem is a bad omen for a deal to come to fruition, as Skubal to Chicago isn't looking likely at all.

Cubs face tricky Tarik Skubal trade problem at deadline

"The Cubs have the most acute need, but their system isn't close to as healthy as the Dodgers', and gutting it for a wild-card berth is tricky business," Passan writes.

While the Cubs' need in the rotation might be greater than some of Skubal's top suitors in the trade market, like the Los Angeles Dodgers, Milwaukee Brewers, and Atlanta Braves, the Cubs have a different problem.

Thanks to their weaker farm system, the Cubs really don't have the capital to spend on Skubal. Sure, they could pawn off a fortune to land him, but as a one-year rental, that would be a massive mistake.

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Making such a blockbuster deal as a Wild Card team would be an even greater mistake. The Cubs should not be spending all of their capital on a rental while they're still a Wild Card team.

Even if they were to take the NL Central lead over the Brewers and own a first-round bye spot by the deadline, spending such a fortune on Skubal might be a mistake.

This is a tricky problem for the Cubs, as the theory of adding Skubal, a back-to-back Cy Young winner, is very sound. But the actual cost and the risk the Cubs would be taking make a deal very unlikely to happen.

The Wild Card problem and the Cubs' weaker farm system are a bad omen for a potential Skubal to Chicago deal this summer. Even though the fit makes sense, unfortunately for the Cubs, this trade doesn't look likely.

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