These Cubs have already played their final game in Chicago ahead of the trade deadline

If ever there were a year for Jed Hoyer to throw caution and his own history running the Chicago Cubs front office to the wind and go big at the trade deadline, it's 2026. His team is staring down a crossroads this winter, with key pieces like Seiya Suzuki, Ian Happ and Carson Kelly set to hit free agency. And the objective couldn't be more straightforward: The Cubs have a pennant-caliber lineup and defense; add impact pitching to both the rotation and bullpen, and Chicago can compete with anybody — yes, even the Los Angeles Dodgers and Milwaukee Brewers.

But if Hoyer swings a blockbuster deal for Tarik Skubal, Adrian Morejon or Reid Detmers, it's going to come at a cost. Whether young talent headed out the door in return or underperforming players whose roster spots are at risk once new players arrive, there are several Cubs who could find their tenures on the North Side cut short once Monday rolls around.

C/DH Moises Ballesteros

The Cubs could be tempted to try to hang on to Ballesteros given Kelly's potential to walk this winter. But the veteran shouldn't be too tough to re-sign given how much he's been embraced in Chicago, and in any event, Hoyer also has top prospect Owen Ayers in Triple-A to fall back on. Ballesteros fell out of favor at the big-league level this season and has been scuffling a bit back in the Minors, but his overall MLB numbers paint the picture of a promising young hitter — one who was a consensus top-100 prospect not all that long ago.

Ballesteros comes with defensive questions, but the bat should play. He feels like a piece that Chicago might be able to flip to a rebuilding team for a relief arm, an exchange of value that Hoyer should take 10 times out of 10 given the team's priorities right now.

RHP Colin Rea

Rea has been thrust back into the spotlight amid the rash of injuries that have befallen Chicago's rotation this season. His 2026 campaign hasn't gone nearly as well as 2025, however, with a 4.67 ERA, 4.85 FIP and 6.7 K/9. It feels like almost a foregone conclusion that the Cubs will add not just one but likely multiple starters between now and Aug. 3; if they do, Rea is the natural candidate to get bumped from the rotation. And given his relatively pedestrian stuff, he wouldn't figure to have a spot on the postseason roster in the bullpen. A free agent this winter, he might come back for another go-round in 2027, but that's not guarantee.

INF Pedro Ramirez

This one isn't particularly fair, as Ramirez has been impressive ahead of schedule after the injury to Matt Shaw thrust him into an unexpected role. With Shaw coming back soon, and the infield locked up with Alex Bregman at third, Dansby Swanson at shortstop and Nico Hoerner at second, he feels like a luxury who would best serve the Cubs as trade bait. He wouldn't be the centerpiece of a package for an impact starter, but as a versatile former top prospect with real contact skills at the plate, he could absolutely serve as the second or third player in a deal. That's probably his best path to consistent playing time moving forward, too.

RHP Aaron Civale

It's a surprise that Civale is even on the Cubs in the first place, the result of an almost comical run of injuries to both the rotation and bullpen. And he's served his purpose, backfilling the bulk relief role once Rea, Javier Assad and Ben Brown all got thrust into starting spots. But he's an eminently replaceable arm at this point in his career, and once rotation additions push Assad, Rea or both back into the bullpen, there won't be much place for him.

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