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Chicago Cubs: Who makes the playoff pitching staff?

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Chicago Cubs, Matthew Boyd

In late June, if you were to say that the Chicago Cubs would be dealing with a surplus of pitching heading into the second half of August, you would’ve been laughed out of the room.

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On June 25, the Cubs made a desperation trade with the New York Mets to acquire veteran David Peterson because they literally were struggling to man even a four-man starting rotation.

Ben Brown, who had been carrying an already stressed and strained rotation, had just been put on the IL, downed by what has become a chronic neck issue. A day earlier, Edward Cabrera was placed on the IL as well, after suffering a left hamstring strain while trying to cover first base on a ground ball. Then there were the struggles of Jameson Taillon, who was getting crushed by opposition hitting, posting a 5.92 ERA through 15 starts.

And all of this was on top of having lost emerging ace Cade Horton to elbow surgery just two starts into the season and the setback of rehabbing former ace Justin Steele.

After an aggressive trade deadline, though, the Cubs managed to restock the rotation with veteran starters Kevin Gausman and Clay Holmes, while also adding reliever Ryan Zeferjahn and potential swingman Braxton Garrett.

And now with Cabrera on the verge of his return, with Daniel Palencia and Hoby Milner not too far behind him, and with Brown telling media that he’s “three, four weeks away” from a return, the Wild Card-topping Cubs are facing the dilemma of who makes the cut for the playoffs. Admittedly, it’s a much better problem to have than what they previously had.

“It’s certainly better than the alternative,” Cubs manager Craig Counsell told reporters on Friday. “Absolutely.”

Projected playoff starting rotation

Clay Holmes, Chicago Cubs
Aug 8, 2026; Kansas City, Missouri, USA; Chicago Cubs starting pitcher Clay Holmes (25) looks into home plate before throwing a pitch in the first inning against the Kansas City Royals at Kauffman Stadium. Mandatory Credit: Peter Aiken-Imagn Images

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At this point, the first three spots in the postseason starting rotation are fairly no-brainer selections: Matthew Boyd, Kevin Gausman, and Clay Holmes. Then, there’s plenty to debate over who becomes starter number four.

One could make a case for Cabrera, Shota Imanaga, David Peterson, Colin Rea, or Javier Assad getting that last spot. Cabrera has the more electric stuff, but Peterson is a sinker specialist who, when right, is the ideal Cubs pitcher. Imanaga has been this season’s most consistently healthy starter, Rea and Assad, however, have shown themselves to be glue when it comes to keeping the back end of the staff together.

Most likely, Counsell’s choice will probably have to do with matchups, with lefties Peterson and Imanaga likely getting the nod against lefty-dominant lineups. Whatever the case, though, the team will have a lot of long-relief options in the bullpen throughout the postseason.

Projected playoff bullpen

Daniel Palencia, Chicago Cubs
Oct 2, 2025; Chicago, Illinois, USA; Chicago Cubs pitcher Daniel Palencia (48) reacts against the San Diego Padres during game three of the Wildcard round for the 2025 MLB playoffs at Wrigley Field. Mandatory Credit: David Banks-Imagn Images

And, speaking of the bullpen, that might make for some even tougher decisions.

Assuming that four of the five from Cabrera, Peterson, Imanaga, Rea, and Assad are used as relief, the Cubs would have just five spots left in the bullpen.

If healthy, Palencia, Milner, and Jacob Webb are shoo-ins. Counsell would also probably choose between Ryan Rolison and Caleb Thielbar as the second southpaw full-time reliever.

And that last spot? That’s the wild card in all of this.

Brown and Steele, if healthy, could be quality additions for a postseason run. Trade deadline acquisition Zeferjahn has the impact arm to make a playoff splash. Shelby Miller and Hunter Harvey could also be healthy enough to come off the IL by then. One also has to consider the arms who’ve helped hold together the bullpen after the waves of injuries, like Trent Thornton and Aaron Civale.

“There’s no givens here—you don’t just step back into your role,” Brown recently told reporters, referring to his role upon return from injury. “This is a really talented team There’s not a lot of spots available on this team. I’ve got to go out there and pitch well to earn my opportunity to pitch in September and in the playoffs.”

The Cubs now have a lot of pitching depth, with some quality veteran arms helping make the case for a deep playoff run. Time will tell if this all pans out.

The post Chicago Cubs: Who makes the playoff pitching staff? appeared first on ChiCitySports.

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