Former MLB Exec Pitches Cubs Blockbuster with Pirates to Address Pitching Woes

The Chicago Cubs and Pittsburgh Pirates could be great trade partners.

Jun 30, 2021; Denver, Colorado, USA; A general view of a Pittsburgh Pirates glove and hat in the eighth inning against the Colorado Rockies at Coors Field. | Isaiah J. Downing-Imagn Images

It is no secret that the Chicago Cubs are on the lookout for pitching help ahead of the MLB trade deadline this year.

They could use some reinforcements at the backend of their bullpen, but most of their focus is going to be on the starting rotation, where injuries and ineffectiveness have plagued the unit.

The loss of Justin Steele to a season-ending injury is a big one to overcome. Shota Imanaga was also sidelined for a period of time and now veteran Jameson Taillon is on the injured list as well.

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Matthew Boyd has been excellent as a frontline producer throughout 2025, but Cade Horton, Colin Rea and Ben Brown have had their inconsistencies filling in behind the free agent addition and Imanaga.

Ideally, the Cubs will be able to acquire a pitcher with front end stuff, possessing the ability to start postseason games for the team.

There aren’t many players who fit that profile who are expected to be available, but one who could be on the move resides in their own division.

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Rumors have swirled that the Pittsburgh Pirates could be open to moving starting pitcher Mitch Keller in the right deal.

What could that deal look like?

In a recent piece, Jim Bowden of The Athletic (subscription required) shared five MLB trade deadline deals he would like to see.

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An intra-division trade between Chicago and the Pirates made the list, with Keller heading to the Cubs in exchange for top prospect, outfielder Owen Caissie and infield prospect Christian Hernandez.

This is a proposal that address major weaknesses for both franchises.

Chicago needs help on the mound. While Keller’s win/loss record is far from great, he is a reliable innings eater capable of producing like a No. 1 or 2 starter in a rotation. His floor is as a middle-of-the-rotation guy.

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As for Pittsburgh, they are in desperate need of offensive help, which has been the case for years.

Acquiring Caissie, whom Bowden has stated is the most MLB-ready prospect who could be on the move, would address that need long-term. He has shown incredible power at Triple-A Iowa this year and could be an everyday contributor for the Pirates right off the bat.

Hernandez has the skills to be a speedy top of the order hitter, already stealing 36 bases this season with a .272 batting average in High-A.

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