Cubs 2025 Winter Meetings Primer: Rumors, Schedules, and Recent History

[Jason Ross]

Image courtesy of © Kamil Krzaczynski-Imagn Images

For many consumers Black Friday and Cyber Monday signal the time period in which it is time to "shop until you drop", buying holiday gifts and presents for the people we find important in our life. While MLB team's don't have a Black Friday discount sale, they do have their own version of a spend-a-thon, and it's during the annual Winter Meetings.

Every year, teams, agents and players gather for a few days in December, and because of the proximity to each other, many of the year's biggest free-agent deals and trades are consummated at this event. Last year, for example, Juan Soto signed with the New York Mets on the largest contract in professional sports history while in Dallas for the 2024 version of the Winter Meetings. Though that won't happen again, what this means is that the Chicago Cubs will likely take part in some of this action next week. What, then, should we expect from the North Siders? 

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When: Monday, December 8th - Wednesday December 10th
Where: Orlando, Florida

Great news for anyone (like myself) who lives on the East Coast! Trades, signings and the like sometimes break at late hours during the Winter Meetings, and in years' past, when they have been held out West, it wasn't uncommon to wake up to breaking news. Just last year, the news that the Cubs signed starting pitcher Matthew Boyd broke at 3:21 am EST. So, while we shouldn't expect the action to entirely die down at night, we're probably in for a slightly-less-late new cycle than when they meetings have been held in San Diego or Dallas.

Monday and Tuesday will be full of rumors, and Wednesday will have its' fair share of smoke, it will also be the day of the league's annual Rule 5 Draft, in which teams will begin to fill out their 40-man-rosters from other team's minor-league ranks. Not all is lost after Wednesday, as a slew of moves will happen afterwards, with the groundwork for them being laid over the course of the previous few days. A good example of this: the Cubs' eventual trade for Astros' outfielder Kyle Tucker, which happened shortly after the close of last year's Winter Meetings.

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How should you follow the action?
Social media is your best friend and worst enemy for this. If you know who to follow and listen to (either on X/Twitter, BlueSky or YouTube) you can be among the first of your friends to break the news that something went down. Any of the big names, such as Jon Heyman, Jeff Passan, Jon Morosi, or Ken Rosenthal can be highly trusted to post the truth (Bob Nightengale of USA Today is a little more hit-and-miss than others). Some of the more local outlets that can be trusted include Brett Taylor and Michael Cerami of Bleacher Nation (and, if you're looking for non-Cub sources, every team has their own version of Bleacher Nation!), Jesse Rogers, Dave Kaplan or Bruce Levine. 

Be careful out there, however. Smaller accounts with low follower counts could simply be clout-chasing for clicks or trying to purposefully deceive. A good rule of thumb: always look to see who's following these accounts. Do they have anyone you've heard of following them? No? Best to read things with a heavy hand of "skepticism" then.  It's a fun time. Rumors are going to fly fast. Just be careful — some of the hardest to spot are the fakes who are just a letter or so different in their screen name from someone you really trust. Just be cognizant and keep an eye out for the false flags, but have fun following the flow of rumors, too.

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What are the Cubs going to do with their rotation?
There's a good chance that the Cubs will look to solve the hole in their starting rotation during these four days. While it seems unlikely that Japanese star pitcher Tatsuya Imai will sign during the Meetings, most of the rest of the starting pitching market is likely to heat up now that Dylan Cease has set the market. Framber Valdez, Ranger Suarez, Michael King and others who may be on the Cubs' radar will likely come off the board soon.

Some have fear with how much the team is willing to spend regarding a recent handful of cost-cutting measures over at Marquee Sports Network, also owned by the Cubs' ownership group, but those fears are just that: fears (as of now). If these fears are a reality, it may push the Cubs into a trade-scenario where they look into cost-controlled starting pitching such as the Miami Marlin's Edward Cabrera or the Washington Nationals' MacKenzie Gore. A trade may not fully materialize at the Meetings, instead taking a day or two beyond Orlando to complete (like their trade last offseason), so it may be a few days before we see the fruits of their efforts on this front come to fruition.

Don't be entirely shocked to hear at least one crazy report connecting the Cubs to someone like Tarik Skubal, either. While it's far-fetched and the price would be astronomical, there are those who speculate he could be available a year prior to hitting his own free agency. Could the Cubs enter this sweepstakes? Absolutely, even if it's unlikely. 

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The Cubs still need to fill out a bullpen, but who will they get?
The team jumped pretty quickly into the reliever market, nabbing righty Phil Maton a few days ago on a two-year deal, but the Cubs are clearly not done filling out their thing bullpen. While they were connected to Ryan Helsley, he signed with Baltimore over the Thanksgiving holiday weekend, and reliever-ace Devin Williams is now off the board, taking his talents to the Big Apple, so the team is going to have to look elsewhere for help. A few names to follow in the back--of-their-pen search could be the Tampa Bay Rays' Pete Fairbanks, the San Diego Padres' Robert Suarez, or a reunion with Brad Keller. All three would require more than one year, but all three would add velocity and whiffs to a pen that needs it.

Don't think the Cubs will only be looking for high-leverage help, though. Chicago needs to fill out their entire bullpen depth chart. They will probably look at some mid-level pitchers (i.e. Kyle Finnegan, Luke Weaver, etc), some left-handed pitchers to replace outgoing Caleb Thielbar and Drew Pomeranz, and some sleeper names, like reuniting with Mark Leiter Jr. or signing Evan Phillips, who is recovering from an injury and won't be ready until mid-year. When it comes to the relief market, I would assume anyone could be a fit.

The Rule 5 Draft on Wednesday will also give the Cubs an opportunity to find some diamond-in-the-rough types as they look to round things out. In 2025, the Cubs selected Gage Workman, an infielder from Detroit, during this event. That did not work out for the team, but I wouldn't be surprised to see them find an arm they think they can mold into a useful bullpen piece.

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Are the Cubs looking to add to their offense?
The Cubs are almost assuredly going to say goodbye to outfielder Kyle Tucker. The team does not seem interested in matching the free agent's price tag and instead appears happy to recoup the compensation pick. With young hitters Owen Caissie and Moises Ballesteros in the fold, as well, they seem poised to let the rookies take the designated hitter spot and run with it. That said, if the Cubs decide to go the trade route (moving, for example, Caissie in a trade for Cabrera) and move one, or both of their young hitters, could they find common ground with, say, Kyle Schwarber and bring the lefty home? Stranger things have happened!

More than likely, however, the team will look into finding a Justin Turner replacement. Turner did post a 112 wRC+ against southpaws, but most would agree that his season left plenty on the table, and an upgrade would be in order. If the Cubs want another veteran, Paul Goldschmidt could make sense in this role. 

The team could also look to the IFA market, with two Japanese stars, Munetaka Murakami and Kazuma Okamoto, highlighting the class. Both offer power potential and the ability to play some first and third base. Neither projects as purely platoon options, and both would require commitments that appear to be well north of $15 million per year. Is the team looking to find someone who's capable of displacing Caissie or Ballesteros as their primary DH? 

Korean Infielder Sung-Min Song could be another intriguing IFA for the team. Song does not look to be as in-demand as his two Japanese counterparts, but offers a better glove and some surprising pop. The lefty wouldn't solve the team's platoon issue, but could add a fun option off the bench. 

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The Winter Meetings will be a time in which, at least, some of these questions are going to be answered, but don't expect them all to be solved. Regardless of what happens, the Cubs will likely make a move or two. Matthew Boyd was signed last year and the framework for Kyle Tucker laid. Will this be as fruitful of a year? For the Cubs' sake, hopefully — the team cannot rest on their laurels and squander the 2026 season coming off a 92-win year. The time to add and improve is now.

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What do you think the Cubs will do during the Winter Meetings? Would would like to see them do? Sound off in the comment section below with your personal hopes, wishes and wants!

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[Bertz]

You've made this point previously but something worth noting is there wasn't even a whiff of Kyle Tucker news before the start of last year's meetings.  The expectation was the team was going to focus on pitching, and Max Fried sounded like the top realistic target.  So while we think we know the state of play it's good to keep an open mind to new info.

That said based on what we think we do know I suspect it's going to be a fairly quiet meetings for the Cubs, I think they come away with a reliever or three and that's it.  My gut says Imai is at the top of their SP wish list right now and that bidding likely won't be settled for a few weeks, which makes it hard to move on too much else.  We likely get more clarity on direction as pieces come off the board, but I expect that to be the main takeaway.  

[Jason Ross]

1 minute ago, Bertz said:

You've made this point previously but something worth noting is there wasn't even a whiff of Kyle Tucker news before the start of last year's meetings.  The expectation was the team was going to focus on pitching, and Max Fried sounded like the top realistic target.  So while we think we know the state of play it's good to keep an open mind to new info.

That said based on what we think we do know I suspect it's going to be a fairly quiet meetings for the Cubs, I think they come away with a reliever or three and that's it.  My gut says Imai is at the top of their SP wish list right now and that bidding likely won't be settled for a few weeks, which makes it hard to move on too much else.  We likely get more clarity on direction as pieces come off the board, but I expect that to be the main takeaway.  

This is generally how I'm viewing the meetings as well. I think the Cubs are a "groundwork" team at the meetings and less of an "action" team at the meetings. For example that Kyle Tucker trade - I think a lot of leg work for that was done in Dallas last year. So whatever the Cubs do this offseason, I think the leg work will happen Monday-Wednesday but the fruits will pay off later. 

My guess is close to yours; I think we'll see one reliever added, the Cubs will be connected to at least one very fun name in one way or another (think like a Nightengale post that suggests the Cubs have had conversations with Detroit over Skubal) that never goes anywhere, and maybe a report that they met with Boras and Imai. Beyond that, I think the actionable items will be the week leading into the holiday where we see the trade they were really working on or the Imai signing pop.

[Victor Reichman]

Tucker should not even be considered. Price and length are way too high and long.  Unless it was for an earth shocking deal, I wouldn't trade Cassie. He has lots of pop and fielded very well, actually better than Tucker for his short time. 

I also don't understand why Keller isn't a priority. He seemed to enjoy his stay and may even give a little home town break as we took a chance with him. Thielbar and Pomerantz should also be considered for a return. The Cubs made the playoffs last yr., were only 5 games behind the Brew who had the best record in the NL. They need to make adjustments, but they are close with Steele coming back, Horton hopefully available for the whole year. The Cubs bats slumped at the end, but the pitching wasn't bad at all.

 

[Illiterate Scholar]

I predict Jed leaves Wednesday talking about the "productive conversations" and "groundwork" and people will have thoughts.

In all seriousness, I'd be curious to learn how close this FO views Imai and, say, King. Like is there still a chance they could sign King any day now for the right deal, or are they waiting to woo Imai. 

[JunkyardWalrus]

I still wonder what they do with Alcantara, I never see him mentioned with Cassie for the plans next year, even though he’d a RHH that can play CF and I don’t believe has options left. 

[Illiterate Scholar]

30 minutes ago, JunkyardWalrus said:

I still wonder what they do with Alcantara, I never see him mentioned with Cassie for the plans next year, even though he’d a RHH that can play CF and I don’t believe has options left. 

I won't pretend to be an expert on why but apparently he is a unique situation and will have a 4th option year, the last year being 2026.

[Jason Ross]

45 minutes ago, JunkyardWalrus said:

I still wonder what they do with Alcantara, I never see him mentioned with Cassie for the plans next year, even though he’d a RHH that can play CF and I don’t believe has options left. 

My assumption as of today is that he will fill a 4th OF role and somewhat of a a platoon situation with Pete Crow-Armstrong.