The Chicago Cubs are expected to make their biggest moves on the trade market this offseason, rather than diving into the deep end of free agency. With prices for starting pitchers and relievers climbing fast-especially after Dylan Cease landed in Toronto and Devin Williams inked a three-year deal with the Mets-it’s no surprise the Cubs are looking for value through trades. Their early signing of Phil Maton was a smart, low-risk move, but it might also be the only dip into free agency we see from Jed Hoyer and his front office this winter.
As the Winter Meetings approach, ESPN’s Jeff Passan and Kiley McDaniel released a list of 25 players who could be on the move this offseason, complete with odds on whether those deals actually happen. What stands out isn’t who’s on the list-but who’s not.
The Cubs, despite being in the thick of their competitive window, weren’t mentioned as a fit for any of the names discussed. That’s a bit of a head-scratcher.
We’re talking about players the Cubs have been tied to in recent months-arms like Joe Ryan and Pablo Lopez from the Twins, MacKenzie Gore from the Nationals, and Edward Cabrera and Sandy Alcantara from the Marlins. These are controllable, high-upside starters who would fit perfectly into the Cubs’ long-term plans. Yet, none of the insiders seem to view Chicago as a serious suitor right now.
So, what gives?
It might have something to do with how the Cubs approached the trade deadline this past summer. They had opportunities to land cost-controlled pitching but refused to part with top prospects like Matt Shaw, Owen Caissie, Moises Ballesteros, or Cade Horton.
And that wasn’t just stubbornness-it was strategic. Shaw and Horton played key roles during the Cubs' playoff push, and it’s clear the organization sees them as foundational pieces moving forward.
That same logic likely applies this offseason.
Still, if the Cubs remain unwilling to move Caissie or Ballesteros-two players they view as future offensive cornerstones, particularly with Kyle Tucker’s production needing to be replaced-it’s tough to see how they land a top-tier starter via trade. Especially when Jaxon Wiggins, one of their top pitching prospects, also seems off-limits.
That leaves the Cubs in a tricky spot. The free-agent market is thinning out fast, and the top-tier trade targets are drawing interest from more aggressive teams.
Outside of the Maton signing, there hasn’t been much urgency out of Chicago’s front office. And while patience can be a virtue, it can also leave you empty-handed.
The Cubs aren’t in rebuild mode anymore. They’re in the middle of a window where adding the right arm or two could push them from playoff hopeful to legitimate contender.
But to get there, they’ll need to make some tough decisions. Holding onto prospects is great-until it costs you the chance to win now.
With the Winter Meetings just around the corner, the clock is ticking. The Cubs have the assets.
They have the need. Now it’s just a matter of whether they’re willing to make the kind of move that signals they’re ready to go all in.