Chicago Cubs Can Strengthen Rotation by Pursuing This Pittsburgh Pirates Star

The Chicago Cubs need at least one more starting pitcher at the trade deadline, even with the return of Shota Imanaga.

The season-ending arm injury to left-hander Justin Steele made that a necessity. Jameson Taillon, Matthew Boyd, Colin Rea, Cade Horton and Ben Brown did solid work keeping things together with Imanaga.

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Help is still needed and it likely isn’t coming from the minor league system. Horton is the only homegrown starter.

The Chicago Cubs have been connected to several starters as the MLB trade deadline approaches, most notably Miami’s Sandy Alcantara. Recently, Ken Rosenthal of The Athletic (subscription required) highlighted a Pittsburgh Pirates starter that could be available at the deadline.

No, not that one. Mitch Keller.

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Rosenthal admitted it would be odd for the Pirates to shop the 29-year-old. The Pirates thought enough of him to sign him to a five-year, $77 million deal before the 2024 season. He was an All-Star in 2023, went 13-9 that season.

With the debut of Paul Skenes last season, the pair were seen as a quality one-two punch for years to come.

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But, Keller’s salary, as Rosenthal pointed out, occupies 20% of the Pirates’ payroll this season and the salary splits only go up in 2026 and beyond. If the Pirates don’t want to boost payroll, they may be forced into a dilemma about how to handle Keller’s contract and still field a competitive team.

That’s where a trade might come in and where the Cubs could pounce. Keller is under team control for three more years because of the contract. Based on Rosenthal’s report, Keller is due less than $50 million over the coming three seasons.

Surely that’s a cost the Cubs can afford to pair a young starter with Imanaga? It likely wouldn’t cut that deep into any pursuit of outfielder Kyle Tucker in the offseason and Keller would be off the books by the time outfielder Pete Crow-Armstrong is due his extension.

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Keller fits the need and cost. The question is whether he’s worth it?

Entering this weekend’s action he was struggling. He led the Majors in losses with a 1-10 record and a 4.02 ERA. This after winning 24 games combined in 2023 and 2024. The upside is Keller generally avoids injury and has made at least 30 appearances each of the last three seasons.

It will be up to the Cubs to determine if Keller is worth it, should he hit the market.

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