The Chicago Cubs may be in the market for a splashy pitching upgrade at the 2026 MLB trade deadline, but the path to Tarik Skubal is a rough one.
Chicago is sitting as a Wild Card team right now, though it’s still close enough to the Milwaukee Brewers in the NL Central to keep the division race in play. That makes the Cubs buyers, and it also puts their pitching needs front and center. Both the rotation and the bullpen could use help, which is why a name like Skubal naturally comes up.
The problem is what it would take to get him.
ESPN’s Jess Passan pointed to the issue that could shut this down before it ever gets serious: “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.
That’s the heart of it. The Cubs may need a starter as badly as anyone, but unlike some of the other teams that could chase Skubal - the Los Angeles Dodgers, Milwaukee Brewers, and Atlanta Braves among them - they don’t have the same kind of farm system depth to lean on. That leaves Chicago in a tough spot if the asking price gets massive.
And it would get massive.
Skubal is a back-to-back Cy Young winner, which makes the idea of adding him easy to understand. But he would also be a one-year rental, and that changes everything. For a team still sitting in Wild Card territory, paying that kind of premium would be a huge gamble.
Even if the Cubs were to climb past the Brewers and into first place in the NL Central by the deadline, the cost still might be too steep. The fit is obvious.
The logic is obvious. The risk, though, is just as obvious.
Right now, that combination makes a Tarik Skubal deal to Chicago look unlikely.
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