For the Chicago Cubs, the time to act is right now if they want to upgrade their starting rotation. While Shota Imanaga and Matthew Boyd have emerged as a solid top duo, the rotation as a whole lacks the depth and firepower seen in other National League contenders. It’s especially glaring when compared to the Milwaukee Brewers, whom the Cubs will face in a high-stakes series starting Monday.
With the trade deadline looming on Thursday, Chicago risks falling behind if they don’t secure additional pitching help. Yes, the market is thin, but one surprising source of help could come from inside the division.
Mitch Keller of the Pittsburgh Pirates is one of the top names potentially available. He’s been a workhorse this season, logging 125 innings with a 3.53 ERA over 21 starts, and he’s under team control through 2028. That makes him an appealing, long-term upgrade for a Cubs staff in need of stability.
On Monday, Jim Bowden of The Athletic responded to a fan-submitted trade proposal that he believes is a “perfect fit” for both franchises. The deal? The Cubs receive Mitch Keller and lefty reliever Caleb Ferguson, while the Pirates land outfield prospects Owen Caissie and Kevin Alcántara — both seen as potential long-term replacements if Kyle Tucker walks in free agency.
“This trade idea just makes too much sense for both sides,” Bowden wrote. “The Cubs fill critical gaps in the rotation and bullpen, while the Pirates add two outfielders who could make an immediate impact.”
The move wouldn’t come without risk — especially with Keller owed $55.7 million from 2026 to 2028, a contract the Cubs would likely take on fully. But with a playoff push in sight and long-term pitching help at stake, it may be a gamble the Cubs are ready to make.
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