MLB Trade Talks — How aggressive will Jed Hoyer and the Chicago Cubs be this offseason? How deep are they willing to wade into free agency to rebuild their rotation ahead of next season? Can we expect multiple impact starters, or is it going to be one primary target and then some fill-ins? These are all questions we have no real answer to as things stand on November 9, the first day of the 2026 GM Meetings.
One thing we do know, however, is that if the Cubs are going to successfully rebuild their rotation this offseason, it’ll likely require a combination of free agency and trade.
The reason for that is the sheer volume of starters who’ve escaped Chicago via free agency: Clay Holmes, Kevin Gausman, Shota Imanaga, Matthew Boyd, David Peterson, Colin Rea, and sort of Jameson Taillon (and that excludes Cade Horton, who will miss most of the year).
Free Agent Price Tag Projections on Outgoing Cubs Free Agents
To that end, I have a new rumor/piece of reporting to share, via Jon Morosi (MLB Network), which is a bit of a mixed bag … if we buy it.
MLB Trade Talks Heating Up?
First, the more exciting component on the latest MLB trade talks, via Morosi:
“MLB team officials have told me in recent days that their trade conversations are more advanced than is typical by this point in November. The GM Meetings are often a venue for preliminary talks, but it would not surprise me if there is a deal or two this week.”
This is not at all surprising*, given the impending lockout, but it is certainly an encouraging thing to hear, not only for the Cubs, who need to be aggressive in the trade market this offseason for the reason I pointed out above, but also for those of us hoping November is an exciting month of transactions ahead of what is going to be a brutally bad lockout which starts three weeks from tomorrow.
*Not surprising for this offseason. In a normal offseason, you would very much not expect any trades to go down this early.
I will add that I have heard a similar story spun on the free agent side, with comments from people in the industry that both teams and agents alike are sprinting to see what can get done before the lockout. The prevailing theory there is that any money locked in before the new CBA could sidestep (at least for a little while) any new, strict spending rules. I don’t think anyone knows any of that for sure, but that’s the general tenor of the conversations I’ve had.
Now, the second, slightly trickier part of the latest MLB Trade talks, also via Morosi later on:
“(I’m) Hearing MLB trade candidates with 1 year of control left — Logan Gilbert, Steven Kwan, Joe Ryan, Sandy Alcántara, et al — are unlikely to be moved for prospects this month, because teams aren’t sure what kind of 2027 season to expect. However, sources say pending free agents could be moved *for each other* as a way to balance the risk.”
Now, there are a couple of ways to take this.
On the one hand, sure. We can all see the logic of that potentially self-inflicted limitation, and it’s not difficult to extrapolate the reasoning therein: Buyers will reduce their offers on any player citing the potential for a lost season, while sellers will balk at reduced prices, citing the last lockout’s result (a full, albeit calendar-condensed, season). Like, okay. Sure. Maybe.
But on the other hand, that cuts both ways. If there is no season (or a partial season), this may be a seller’s last good chance to extract value from certain player assets. They can still try to maximize the return, and interested buyers will still be willing to roll the dice.
But you know what this sounds most like to me? Just boilerplate leverage narratives. Maybe it’s buyers wanting sellers to know, “Hey, your prices are not considering the lockout.” Or sellers wanting buyers to know, “Hey, we’re not going to move these guys for pennies based on the POTENTIAL of there MAYBE being a lockout.”
That folds into the first point, sure, but I just don’t buy that it’ll actually prevent any deals from getting done. Perhaps that’s informed by my own blind optimism that there will be plenty of baseball in 2027. But I guess we’ll see.
Now, as for that other half of that quote … no, that’s nonsense. I’m not saying Morosi is wrong to report it or didn’t actually hear that exact thing from an organization. But MOST teams trading away one-year players are sellers looking to the future … not teams that just want to get more one-year assets, even if they otherwise fit positionally. It’s not that I can’t conjure up some scenario where it might make sense, but as a MORE likely outcome than just trading a one-year player for prospects? Nah. I don’t buy that.
And all of that brings me to the Cubs.
Miami Marlins pitcher Sandy Alcantara | Jim Rassol-Imagn ImagesCubs Trade Market
As I’ve mentioned twice now, I believe the Cubs will be active on the trade market this offseason. And all four of the players Morosi mentioned — Logan Gilbert, Steven Kwan, Joe Ryan, Sandy Alcántara — made it onto my list of preferred Cubs trade targets for 2027. You can probably add Griffin Jax (SP, Rays) and MacKenzie Gore (SP, Rangers) to that list, as well.
The Top 17 Cubs Trade Targets for 2027
If none of those guys are made (reasonably) available this month, the Cubs will be disappointed, and I’ll be surprised. Again, I just don’t buy it. We’ll see, but I think this month is going to end up busier than we expect.
And while most of my confidence there revolves around free agency and what happened during the last free agent period before a lockout (2021) …
Overall:
Total Big League Free Agent Deals: 50 Total Money Guaranteed: $1.91 billion Median Deal: $16.75 millionBy Total Value:
$300M+ deals: 1 (Corey Seager) $100M+ deals: 6 $50M+ deals: 13 $25M+ deals: 18 $10M+ deals: 29 Less than $10M deals: 21By Length:
1-year deals: 21 2-year deals: 11 3-year deals: 5 4-year deals: 7 5-year deals: 3 6-year deals: 1 7-year deals: 1 8-year deals: 0 9-year deals: 0 10-year deals: 1… I think the trade market will follow suit, perhaps especially because this is such a weak overall free agent class.
Consider for a moment Steven Kwan and the Guardians.
Kwan, 29, is a left-handed, high-contact, high-OBP bat with one of the most consistent resumes in baseball and just one year of team control remaining. He is theoretically available alongside only two solid outfield free agents, Seiya Suzuki and Randy Arozarena. That’s pretty much it. Do we really expect the Guardians, who often follow the same formula as the Brewers and Rays by refusing to let the value of their expiring assets go unextracted, to just defiantly make him unavailable? Do we think the horde of outfield-needy (or offense-needy) teams out there are going to risk not getting one of the two solid bats in free agency? I don’t.
This stuff always comes down to supply, demand, and timing. And while this winter is going to look different, those factors still pit teams against each other under the exact same circumstances. So, I just don’t buy that these guys are effectively unavailable, as the report implies.
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