The Chicago Cubs limped into the NLDS with a starting rotation limited to two reliable pitchers and a bullpen held together by hopes, wishes, and the managerial maneuverings of Craig Counsell.
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To their credit, though, they almost worked through their glaring weaknesses by taking the Milwaukee Brewers to Game 5 after falling behind 0-2 in the best of five series. But there was no way to walk away from the NLDS loss not recognizing that they needed to fortify their pitching across the board, starting with their rotation.
To the Cubs’ credit, they didn’t lean on the excuse that they were missing an injured Cade Horton and Justin Steele. It would’ve been easy to sit back and do nothing, depending on the return of Horton and Steele in 2026 to be the big offseason pitching additions for a second straight playoff push. The front office, however, has come right out and declared impact pitching to be their primary focus this winter.
The question, though, is where to find it and how far Cubs ownership is willing to go to get it.
Looking for high-end starting pitching
Jul 18, 2025; Chicago, Illinois, USA; Chicago Cubs President of Baseball Operations Jed Hoyer walks on the sidelines before a baseball game between the Chicago Cubs and Boston Red Sox at Wrigley Field. Mandatory Credit: Kamil Krzaczynski-Imagn Images
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There are several front-of-rotation starters currently on the free agent market and Chicago was reportedly in on Dylan Cease before the Blue Jays dug a little deeper into their pockets to snatch him up. Framber Valdez, Ranger Suarez, Michael King, Zac Gallen, Merrill Kelly, and the Japanese import Tatsuya Imai are still available and the Cubs have had reported interest in several of them.
But would it be wise to bet on the Cubs laying out big money on a long contract for any pitcher? They haven’t done that since they signed Yu Darvish to a 6-year, $126 million contract back in 2018– and they ended up trading him just two years into that contract.
It’s much more likely that the Cubs will look for their impact arm via trade.
A trade is more likely
Chicago Cubs president of baseball operations Jed Hoyer talks to the media after introducing pitcher Shota Imanaga (not pictured) during a press conference at Loews Chicago Hotel. Mandatory Credit: Kamil Krzaczynski-Imagn Images
They tried to do that last winter before getting cold feet on a Jesus Luzardo deal with the Marlins. But this year might be different. They know (and everybody knows) that the team is really close to moving from a playoff contender to a World Series contender. Right fielder Kyle Tucker will be gone this winter and a good chunk of the roster is due to become free agents after next season. If some high-end talent is not acquired this winter, while there’s the best chance to win, the entire Cubs organization will be raked over the proverbial coals.
But what would a trade for high-end pitching cost, especially considering that the Cubs will be looking for a starter with years of team control ahead? It’ll be uncomfortably expensive.
The cost in trade capital
Syndication: The Des Moines Register Iowa Cubs’ Owen Caissie (17) makes his way to the dugout on Friday, March 28, 2025, at Principal Park in Des Moines. © Cody Scanlan/The Register / USA TODAY NETWORK via Imagn Images
Jake Misener of Cubbies Crib recently proposed a trade for a young, front-of-rotation starting pitcher that seems pretty much right on the money.
In his proposal, the Cubs would get SP Edward Cabrera and RP Anthony Bender for an absolute haul of Cub prospects– OF Owen Caissie (no. 1 Cubs prospect), P Jaxon Wiggins (no. 3 Cubs prospect), IF James Triantos (no. 10 Cubs prospect), and P Ben Brown.
Giving up three top 10 prospects– including their no. 1 pitching prospect– along with a young arm with big potential up side is a high price to pay. But Cabrera, who many believe has turned the corner on his development, could be worth it. It also doesn’t hurt that the 27-year-old is under team control through the 2028 season and will be making less than $2 million in 2026 before becoming eligible for arbitration. Bender, meanwhile, would be a welcomed addition to a bullpen in need of a full-on rebuild.
Would the Cubs go for such a deal– or any deal that demands so much in trade capital?
They would, if they’re serious about adding a core component to their starting rotation. A budget-friendly, team-controlled starter won’t come cheap and there’s no way around having to trade away plenty of young talent to get one.
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