Starting Pitchers That Make Most Sense for Cubs to Acquire at Trade Deadline

The Chicago Cubs have one clear need that has to be addressed ahead of the MLB trade deadline this year: starting pitching.

Losing Justin Steele to a season-ending injury was a significant blow to a team that already have a need for a front-end starter. Shota Imanaga has spent a chunk of the campaign on the injured list as well, making only 11 starts.

The fact the Cubs have been able to survive this long in the starting rotation without them speaks volumes to how productive the other parts of the team have been.

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A lot of credit needs to go to Matthew Boyd as well, who has performed like an ace and been healthy in 2025.

Adding depth to the rotation behind him and Imanaga is a must ahead of the deadline if Chicago wants to truly keep pace with other contenders such as the Detroit Tigers, Philadelphia Phillies, Los Angeles Dodgers and Houston Astros, who all possess dominant aces and front-end starters.

Alas, it takes two to tango.

The Cubs have a need, but they need to find a team that will be willing to match up with them on a trade.

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Who could they target?

Jim Bowden of The Athletic (subscription required) has shared five starting pitchers who would make the most sense as trade targets ahead of the deadline.

“Mitch Keller of the Pirates, Zac Gallen and Merrill Kelly of the Diamondbacks and Edward Cabrera and Sandy Alcantara of the Marlins make the most sense,” the former MLB executive wrote.

Keller, an All-Star in 2023, has been a consistent workhorse for the Pittsburgh Pirates. Prying him from a National League Central rival could be costly, but is under team control through 2028 at an affordable price compared to what other starting pitchers are receiving on the open market.

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Gallen has performed like an ace at points in his career. But 2025 is just not one of those times with a 5.15 ERA, 4.76 FIP and 1.345 WHIP, which would all be single-season worsts along with his 81 ERA+.

But, he does have three top-10 finishes for the Cy Young Award. Set to hit free agency after the season, a change of scenery could help him get on track.

His teammate, Kelly, is also set to be a free agent after the campaign and has made it clear he would like to end his career with the Diamondbacks. 

As consistent as they come over the last few years, he would be a great rental target as really solid No. 2 or No. 3 starter.

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Alcantara is the biggest fish on the starting pitching market. The former NL Cy Young Award winner, when on top of his game, would be the ideal front-end starter to help put Chicago on par with the other contenders.

Acquiring him will not be cheap, with the Marlins likely asking for a massive haul of prospects in return.

Cabrera would be a lot more affordable and is a stuff monster, a favorite in the analytic community. He has produced more than Alcantara this year and is under team control through 2028, providing the Cubs with some stability in their rotation should they be able to land him.

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