The Cubs are heading into an offseason with real work to do, and that creates a tricky squeeze for two former top prospects who may not have much runway left. Chicago has openings in the rotation, plus the need to account for Ian Happ and Seiya Suzuki, and while the front office should be active in free agency and on the trade market, the early signs point to some internal names getting a longer look for 2027.
That’s where the pressure starts to build. The Cubs appear set to give Matt Shaw and Pedro Ramirez expanded roles in the outfield, while Justin Steele’s return gives them a starting point for the back end of the rotation.
Edward Cabrera is also expected to get a shot to win back a spot. But as the roster picture comes into focus, two players on the 40-man roster look like they’re slipping out of the plan.
With a lockout expected on December 2, the Cubs may not have much time to sort out the edges of the roster before the offseason gets interrupted. That makes decisions on Kevin Alcantara and Jordan Wicks even more urgent.
Alcantara finally has an opening in the outfield, but the opportunity hasn’t translated into any real sense that the Cubs are ready to give him a meaningful role. Over the last two seasons, he’s mostly been used as a fourth outfielder, and he’s appeared in just 34 games across that stretch.
The bigger complication is that he’s out of minor-league options, which adds another layer of urgency. If the Cubs run short on time to finish building out the bench, Alcantara could end up sneaking onto the Opening Day roster.
Even so, the current feel is that he’s closer to being a former Cub than a piece of the 2027 mix.
Wicks is in a similar spot, only on the pitching side. The Cubs have a path open for a former first-round pick to grab a rotation job, but he has drifted toward the bottom of the depth chart.
Instead of locking down a steady role, he’s been used as an up-and-down arm for the big league club. He’s made only 12 appearances over the last two seasons, and in 2026 he posted a 10.45 ERA.
Even with Chicago’s need on the mound, counting on Wicks to factor into the 2027 picture feels like a stretch. If anything, he has the look of a player who could be included as the last piece in a trade the Cubs make this offseason.
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Cubs May Already Have A 2027 Outfield Decision Coming Into Focus
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Crow-Armstrong appears likely to be part of that next wave, but Ian Happ and Seiya Suzuki may be headed toward free agency by then, which puts some pressure on the organization to plan early. Two internal names to watch are Josiah Hartshorn and James Triantos, both of whom offer the kind of versatility teams value when roster construction gets tight, with Hartshorns defensive flexibility and recent jump to Double-A standing out and Triantos bringing minor league production plus the ability to move around the diamond. [Read more 🡒]
Cubs Outfield Reality Is Starting To Crush The Dream Options
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Bryce Harper and Ronald Acua Jr. are the kind of names that can ignite a winter, but the reality around both makes those dreams feel remote. Harpers contract is a major obstacle, and Acuas trade status is uncertain enough to make a deal unlikely, which leaves the Cubs pointing toward shorter commitments for veteran hitters and more affordable outfield help on the open market. [Read more 🡒]
Cubs Offseason May Come Down To One Aggressive Pitching Decision
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Drew Rasmussen has emerged as the kind of name that fits that bigger swing, especially with the Rays payroll situation making him a logical trade candidate. For the Cubs, the appeal is obvious: a chance to chase a true No. 1 type rather than patching over their recent pitching issues one piece at a time, even if nothing has been finalized yet. [Read more 🡒]