Cubs Head Into Winter Meetings With Questions, Constraints, and Trade Chips
The Winter Meetings are right around the corner, and if recent history tells us anything, the Chicago Cubs are capable of pulling off a move no one sees coming. Just last offseason, the Cubs stunned the baseball world by trading Isaac Paredes for Kyle Tucker - a blockbuster that took shape during these very meetings. So, if you're expecting a quiet week from the North Siders, think again.
But this time around, the Cubs enter the Winter Meetings in a more complicated spot. They’re coming off a postseason run that ended just one game shy of the NLCS - a sign that this roster is close.
And yet, the path forward isn’t exactly wide open. There are holes to fill, needs to address, and perhaps most importantly, financial questions that could shape what’s realistically on the table.
The Cubs’ To-Do List: Pitching, Power, and Possibilities
Let’s start with the basics. The Cubs need a top-end starting pitcher.
That’s no secret. They also need a right-handed hitting corner outfielder to balance out a bench that leans left.
And while nothing is imminent, they’re keeping tabs on the Alex Bregman situation, just in case his free agency plays out like it did last year - slow and full of surprises.
The urgency is there. After coming so close to the NLCS, the front office knows the window is open. The Phil Maton signing showed a willingness to act early, but it also raised a question: how far are the Cubs willing - or able - to go financially?
That question looms larger after a string of missed opportunities. Over the past week, potential targets like Dylan Cease, Ryan Helsley, and Devin Williams all signed elsewhere.
And once the details of those deals became public, it was clear why Chicago didn’t make a push - the price tags were steep. Add in growing concerns about the financial health of Marquee Sports Network, and suddenly the Cubs’ offseason strategy starts to look less aggressive and more calculated.
If Not Free Agency, Then What?
That brings us to trades - the likely focus for the Cubs at the Winter Meetings. But here’s the catch: making a deal isn’t as simple as picking up the phone.
The Cubs' top-tier prospects - Owen Caissie, Matt Shaw, and Cade Horton - were considered untouchable at the trade deadline, and there’s little indication that stance has changed. If those names remain off limits, the Cubs will have to get creative.
That means exploring deals that involve pieces from the Major League roster, paired with lower-level prospects. It’s not impossible, but it does narrow the field.
Kyle Tucker is no longer in the picture, and with both Ian Happ and Seiya Suzuki holding no-trade clauses, moving either of them would be difficult and unlikely. So, if the Cubs are going to surprise us with a trade, it might come from a less obvious name - like Ben Brown.
Ben Brown: Trade Chip or Bounce-Back Candidate?
Brown is an intriguing case. His raw stuff is electric - some of the best swing-and-miss material in the organization - but his two-pitch mix has limited his effectiveness as a starter at the big-league level. Heading into 2026, he doesn’t have a clearly defined role, and that makes him a prime candidate to be part of a trade package.
If the Cubs are eyeing a cost-controlled starting pitcher - and that seems likely - including Brown in a deal would make sense. He’s Major League-ready, he has upside, and he could be more valuable to another team that sees a better fit for his skill set, whether that’s in the bullpen or as a starter with a refined arsenal.
The Bottom Line
The Cubs are navigating a tricky offseason. They’re close enough to contend, but not without reinforcements.
They have needs, but also constraints - financial and otherwise. And while the Winter Meetings offer a stage for bold moves, the Cubs may have to get creative to make something happen.
Don’t be surprised if trade talks dominate the headlines next week. Whether the Cubs pull the trigger or simply lay the groundwork for bigger moves down the line, one thing is clear: the front office knows the clock is ticking. And with a roster on the brink of something bigger, this winter could be pivotal.