The Chicago Cubs are heading toward a roster shakeup, and Jed Hoyer’s comments about a different-looking 2027 team make that pretty hard to miss. With a big chunk of the pitching staff set to hit free agency after the offseason begins, and with Ian Happ, Seiya Suzuki and Carson Kelly all mentioned as possible departures from the starting lineup, the Cubs are staring at a winter that could leave next year’s club with a very different feel.
That doesn’t mean the whole picture is bleak. The core still looks strong enough to build around, with Pete Crow-Armstrong, Nico Hoerner and Alex Bregman in place.
But there are also real questions hanging over Dansby Swanson, and Michael Busch’s 2026 season was one of the biggest individual disappointments of the year. All of that is unfolding while the Cubs’ contention window remains open.
The good news for Chicago is that there should be room to maneuver. The Cubs have more than $100 million coming off the books this offseason, giving them a chance to attack pitching in free agency.
But free agency won’t be the only way Hoyer reshapes the roster. Trades could be part of the equation, too, and a few names stand out.
Matt Shaw is one of them, even if the Cubs would probably prefer not to move him. Right now, he could be their Opening Day left fielder.
Still, if Chicago goes into the trade market looking for a top-of-the-rotation starter, Shaw is the kind of player who could wind up in those discussions. That said, it sounds like the only realistic path to a deal involving Shaw is if the Cubs are chasing a major pitching upgrade.
Pedro Ramirez is in a similar spot, though he may be a touch closer to untouchable based on how the 2026 season ended. Even so, the Cubs probably wouldn’t be against including him if the return was right, especially if they were dealing for a one of one starting pitcher. Between Shaw and Ramirez, the sense is that one of them could be on the move this offseason.
Kevin Alcantara feels like a much cleaner trade candidate. When Hoyer discussed possible outfield options for next season, Shaw and Ramirez came up - Alcantara did not.
That alone says plenty about where things stand. The signs have been pointing toward Alcantara losing favor with the organization, and with him set to be out of minor-league options next season, the Cubs may be pushed toward making a move.
Jordan Wicks is another name to watch. Chicago probably isn’t eager to deal from pitching depth with so many free-agent arms on the way out, but Wicks still looks like a candidate to go.
The former first-round pick has settled into an up-and-down role over the last two years, and like Alcantara, he will be out of minor-league options next year. That could be enough to seal his fate in Chicago.
In Other News...
Cubs Face A Costly 2027 Pitching Decision Beyond Clay Holmes
The Cubs have some winter homework coming into focus already, and it is not limited to Clay Holmes. Beyond the right-hander's expected choice to test free agency, Chicago also has a cluster of 2027 club options to weigh, giving the front office several decisions to sort out on the pitching side as it looks ahead. Javier Assad, Colin Rea and Jacob Webb have all given the club reasons to think seriously about keeping them around, with each fitting a different need in the staff mix.
Assad's value comes from what he has shown in recent run prevention work, Rea has offered reliability in a useful swing role, and Webb has helped deepen the bullpen with his recent performance. Holmes remains the most complicated case because of the player option attached to his deal and the uneven results he has delivered with the Cubs, but the broader question is whether Chicago can afford to let proven depth walk away when the roster already has enough uncertainty built into it. [Read more 🡒]
Cubs Facing Some Uncomfortable 2027 Bullpen Decisions Already
The Cubs are already staring at some tricky bullpen math for 2027, and it starts with a handful of veterans who may not fit the clubs next wave. Caleb Thielbar, Hunter Harvey, Trent Thornton and Tyler Austin are all on track to reach free agency before that season, and each brings a different reason for Chicago to think hard about the future rather than the recent past.
Thielbar has slipped from the kind of reliable late-inning arm the Cubs hoped for, Harveys value was undercut by another injury-hit season in 2026, Thorntons run prevention has not come with the strikeout punch teams want from a bullpen piece, and Austin has not offered much since his surgery. Put together, it leaves Chicago with an uncomfortable but familiar front-office task: deciding which relievers are worth another chance and which ones are better left off the 2027 plan. [Read more 🡒]
Cubs Still Have One Edward Cabrera Decision Hanging Over This Offseason
The Cubs offseason has already brought a few moving parts, from a batch of international free-agent signings to minor-league deals to Pete Crow-Armstrong earning Baseball Americas Player of the Year honors after a huge 2026 season at the plate. Even with that attention on the future, the front office still has a more immediate pitching question to sort through, and it centers on Edward Cabrera.
Chicago views Cabreras struggles through two lenses, health and delivery, with blister issues and mechanical problems both part of the conversation. The organization has made him one of its pitching priorities this winter, but the lingering question is how much confidence it has in a rebound and what kind of decision it is prepared to make as the offseason keeps moving. [Read more 🡒]