Chicago Cubs won’t even try to land big fish free agent, per insiders

The Chicago Cubs’ season ended after an ugly two-game stomping at the hands of the San Diego Padres in the opening Wild Card series at Petco Park.

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While people may wax poetic about the Cubs’ 2026 run, noting how they battled through some unprecedented injury misfortune to get as far as the opening playoff series, the truth of the matter is that things ended in ugly fashion. Eventually, all of the concerns regarding the roster turned out to be, precisely, the things that brought about their downfall.

And 2027 is shaping up to be even uglier than the end of 2026.

Chicago is set to lose their entire end-of-season starting rotation to free agency (Matthew Boyd, Kevin Gausman, Clay Holmes, Shota Imanaga, David Peterson).

Not going after Tarik Skubal?

Jed Hoyer, Chicago Cubs, MLB trade deadline — Jan 12, 2024; Chicago, IL, USA; 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-USA TODAY Sports

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And if MLB insiders Patrick Mooney and Sahadev Sharma are correct, the Cubs aren’t likely to go big in their pursuit of replacements.

Per Mooney and Sharma in The Athletic:

“With some trade chips still on hand and a vast amount of salaries falling off the books — Roster Resource projects Chicago’s major-league payroll has roughly $110 million in commitments — Hoyer’s group will have to pour those resources into the rotation.

Just guessing that the Cubs won’t be the big-market franchise willing to hand Tarik Skubal the biggest pitching contract ever before the current labor deal expires at 11:59 p.m. ET on Dec. 1.”

It’s disappointing, but not surprising, that Jed Hoyer and the Chicago front office won’t even take a stab at signing an elite-tier pitcher after seeing how this season turned out. However, something clearly has to be done when it comes to restocking the team’s rotation.

The 2027 Cubs starting rotation

Mar 27, 2025; Phoenix, Arizona, USA; Chicago Cubs pitcher Justin Steele (35) pitches against the Arizona Diamondbacks during the first inning at Chase Field. Mandatory Credit: Joe Camporeale-Imagn Images

The possible rotation pieces the Cubs do have returning are iffy and questionable. Justin Steele will come into 2027 after missing two full years due to elbow and flexor issues. Cade Horton may miss the entire season—or at least most of it—after Tommy John surgery. Ben Brown was en route to a breakthrough year as a starter this past season, until he again went down with the same chronic neck issue that has shut him down before. Edward Cabrera was absolutely awful in his first season as a Cub. Javier Assad, meanwhile, has mostly been a reliable presence, but he’s much more of a back-of-rotation starter than a star.

If the Cubs come into the 2027 campaign with a rotation of Steele, Brown, Cabrera, Assad, and Braxton Garrett, you might as well write off a playoff berth.

So, there’s pretty much no getting around it. Chicago needs to dip into the free agency market to fill out that rotation. The question will be whether they can get over their aversion to spending big on free agent pitching or if they’ll again try to find rehabilitation projects and diamonds in the rough on the cheap while just hoping for the best. We all saw how well that worked out in 2026.

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