As the Cubs head toward the finish line, the big-picture questions are already coming into focus. Chicago has pushed its chips in for 2026, but this roster is still headed for a different look this winter, and most of the movement is expected to come on the pitching side.
A large chunk of the names in the rotation and bullpen are set to hit free agency, and while the Cubs have plenty to sort through, they shouldn’t lose sight of Seiya Suzuki either. There’s room to make him a priority while they work on adding arms.
Still, not everyone on the roster is trending in the right direction as the season winds down. A few players are making it harder to imagine them as part of the Cubs’ 2027 plans.
Shota Imanaga is one of four free agents this offseason along with Matthew Boyd, Kevin Gausman, and Clay Holmes. If the Cubs decide they want to bring back at least one arm from that group, Imanaga does not sound like the first name they’d circle. He has been mostly solid this year, but the recent trend line has raised enough concern that Chicago probably won’t be rushing to the front of the line in his market.
Colin Rea’s case feels even more straightforward. For two years, he’s been the kind of pitcher teams love to find in the margins, the steady presence who keeps the staff afloat.
But that run may be close to over. He owns a 4.55 ERA this season, backed by a 4.92 FIP and a 5.58 xERA, and the numbers point in the same direction: the Cubs may have gotten all they’re going to get out of him.
Rea has a $7.5 million club-option for 2027, and the simplest path appears to be moving on while letting Javier Assad handle the swingman role next season.
Kevin Alcantara is another name that belongs on this kind of list. The Cubs could have openings in left field and right field next season, but there’s been nothing to indicate Alcantara is a real candidate for the starting lineup. He could still hang around as a fourth outfielder, but the outlook beyond that doesn’t look strong.
Phil Maton rounds out the group. He’ll be in the second and final year of his contract with the Cubs in 2027, and if his struggles continue after he works back from his current knee injury, Chicago probably won’t wait long before moving on. That kind of decision wasn’t realistic this season, but it’s much easier to picture next year if he doesn’t quickly find his form again.
In Other News...
Cubs Just Made A Bullpen Move That Raises Bigger Questions
The Cubs bullpen picture got a little more complicated this week with the designation of Hoby Milner for assignment, a move that comes after the left-hander had been working his way back from an emergency appendectomy. Milner was reportedly nearing a return from the injured list and had turned in a strong rehab stint at Triple-A, which made his roster status one of the more noteworthy developments on the pitching side.
Instead, the decision suggests the Cubs are weighing more than just Milners recent form as they try to sort out a relief corps that still needs answers. For a team that can use dependable innings in the late-game mix, moving on from a pitcher so close to returning raises broader questions about how the front office is managing the bullpen spot by spot, and what other changes might be coming next. [Read more 🡒]
Cubs Bullpen Suddenly Has Two Intriguing Answers To A Growing Problem
The Cubs have kept getting quality work from their rotation, but the bullpen has been the place where games have started to slip away. Help may be coming from two different rehab tracks in Iowa, where Hoby Milner has been pitching effectively as he nears the end of his 30-day rehab window and Shelby Miller has continued to show encouraging signs in his comeback from Tommy John surgery.
Milner gives Chicago a near-term decision on a left-handed relief option, while Millers work has been louder, with 12 strikeouts in 6.1 innings this month and fastball readings as high as 98 mph. For a bullpen that has been asking for answers, the Cubs suddenly have two relievers trending the right way, even if the timing and fit of each one still need to be sorted out. [Read more 🡒]
Cubs Face Another Carter Hawkins Question As His Stock Keeps Rising
The Astros decision to move on from Dana Brown is the latest reminder of how quickly the GM market can shift, and it inevitably sends the focus back to Carter Hawkins. Around the league, Hawkins is the kind of executive who tends to surface when a front office job opens, and for good reason. Since taking over as the Cubs general manager, he has earned a strong reputation for helping reshape the clubs pitching infrastructure, which has become one of the organizations more encouraging stories.
Still, theres a difference between being a name that gets mentioned and being a realistic departure candidate, and thats where the conversation gets more complicated for Chicago. Hawkins is not expected to leave unless a team is prepared to offer him a clear promotion, but his profile keeps climbing as vacancies emerge. The questions around him now are less about whether hell draw outside interest and more about how the Cubs continue to balance the areas where he has helped most with the internal development and communication issues that still need work. [Read more 🡒]