Cubs, Gallen, and the Winter Meetings Whirlwind: What’s Real, What’s Not, and What Comes Next
Just days before the Winter Meetings officially kick off, the Chicago Cubs found themselves at the center of a fast-moving - and now fast-walking - rumor mill. Reports initially suggested the Cubs were closing in on a multi-year deal with free-agent right-hander Zac Gallen, but that narrative shifted quickly.
According to Bob Nightengale, the Cubs were set to sign Gallen to a deal that would pay him an average of $22 million per year. But shortly after that report gained traction, ESPN’s Jeff Passan countered with a firm update of his own: not only is a deal not done, but Gallen isn’t close to signing one at all.
So where does that leave things? Somewhere between “almost done” and “not even close,” which is exactly the kind of chaos that tends to bubble up right before the Winter Meetings begin. And if this is the early tone-setter, buckle up - it’s going to be a wild few days in Nashville.
The Gallen Fit - Or Lack Thereof?
Even before the conflicting reports, there was a healthy dose of skepticism about Gallen’s potential fit on the North Side. The Cubs have been linked to bigger swings this offseason - including trade interest in Dylan Cease and international buzz surrounding Japanese righty Tatsuya Imai. So, for some fans, the idea of landing Gallen felt a bit underwhelming.
That’s not to say Gallen doesn’t bring value. He’s a durable arm with three top-10 Cy Young finishes and has averaged 32 starts over the past four seasons - a level of consistency that’s hard to find in today’s game. But the recent trendlines are concerning.
In 2025, Gallen posted a 4.83 ERA across 192 innings - a full-season workload, yes, but one paired with declining effectiveness. His strikeout rate dropped to 21.5%, continuing a two-year slide from the 25.1% he posted in 2024 and well below the 26-29% range he maintained from 2019 through 2023. Meanwhile, his walk rate crept above three per nine innings - another red flag for a pitcher whose success has often hinged on command and deception.
It’s not all doom and gloom, though. Over his final 11 starts in 2025, Gallen posted a 3.32 ERA in 65 innings with eight quality starts - a strong finish that at least hints at a possible rebound. But even in that stretch, the strikeout rate hovered in the low 20s, which tempers the optimism.
Is This the Move - Or Just the Start?
If the Cubs were to sign Gallen, and that turns out to be their marquee rotation addition, it would raise questions about the front office’s overall strategy. There’s still a deep pool of arms on the market - including pitchers with higher upside than Gallen, even if they come with more risk. Michael King, for example, has a shorter track record and durability concerns, but his ceiling might be higher.
Then there’s Imai, who remains one of the top international free agents available. The Cubs have shown interest, and if they’re serious about bolstering the rotation with a long-term piece, he still makes a lot of sense. But if Gallen is the move - and no corresponding trade follows - then the focus likely shifts to the bullpen, where the Cubs still have work to do.
What’s Next?
For now, the Gallen-to-Cubs scenario is on pause - if it was ever truly in motion to begin with. Conflicting reports are part of the game this time of year, and until pen hits paper, nothing is certain.
But this much is clear: the Cubs are in the market for pitching, and whether it’s Gallen, Imai, Cease, or someone else, they’ll need to solidify their rotation if they want to contend in 2026. The front office has shown it’s willing to explore multiple avenues - free agency, trades, and international signings - and that flexibility will be key in navigating what’s shaping up to be a competitive and unpredictable offseason.
The Winter Meetings haven’t even started yet, and already the rumor mill is spinning at full speed. Stay tuned - this is just the beginning.