Winter Meetings Wrap: Three Rumors That Should Have Cubs Fans on Alert
The Winter Meetings have come and gone, and for Cubs fans, the takeaway is less about what happened and more about what didn’t. In what’s typically a flurry of trades, signings, and surprise moves, this year’s event in Orlando was unusually quiet.
The Cubs, like many teams, walked away without making a splash. But while they didn’t miss out on any slam-dunk deals, the silence doesn’t mean there’s no reason for concern.
In fact, a few key developments-and some rumblings around the league-could set the stage for a more complicated offseason in Wrigleyville. Let’s break down three rumors coming out of the Winter Meetings that could spell trouble for the Cubs if things don’t break their way.
1. Michael King Rising on Mets’ Radar
From the jump, Michael King looked like a tailor-made fit for the Cubs’ rotation. He’s not without risk-shoulder issues derailed his 2025 campaign-but the upside is undeniable.
In 2024, he made 30 starts and posted a 2.95 ERA with a 3.33 FIP, flashing the kind of top-end stuff that teams crave in the middle of the rotation. And unlike the true aces on the market, King wouldn’t command a nine-figure deal.
That’s exactly why the Cubs had their sights set on him. But now, they’re not alone.
The New York Mets have reportedly zeroed in on King as their top rotation target. With Pete Alonso and Edwin Diaz both departing, the Mets are feeling the pressure to retool quickly, and King fits the bill.
That puts Cubs president Jed Hoyer in a tight spot-especially with the team also eyeing Japanese right-hander Tatsuya Imai. If Imai signs elsewhere or if King comes off the board first, the Cubs could be left scrambling for a Plan B.
Sure, names like Framber Valdez, Ranger Suarez, and Zac Gallen are still floating out there, but the connection to King has been strong. Losing him to a big-market rival like the Mets? That would sting.
2. Red Sox Doubling Down on Alex Bregman
The Cubs’ offense needs a jolt, and Alex Bregman has long been viewed as a potential answer. He’s a proven bat, a clubhouse leader, and even in an injury-shortened stint with Boston, he posted a strong .273/.360/.462 line with a 125 wRC+. That’s the kind of production the Cubs could use in the heart of their lineup.
But if there was ever a window to pry Bregman away from the Red Sox, it may have just slammed shut.
Boston has made it clear they still view Bregman as a key piece, and with other options like Kyle Schwarber and Pete Alonso now off the board, the Sox might have even more incentive to bring him back. Reports indicate that Boston still wants to add two bats, and Bregman remains their top internal priority. That makes it harder to envision a scenario where he ends up in Chicago.
The Cubs have been linked to Bregman more than any other marquee bat this offseason. If Boston locks him up and pivots to fill their other needs elsewhere, the Cubs may find themselves without a clear offensive upgrade in a thinning market.
3. Closer Market Heating Up-and the Cubs May Be Falling Behind
If there’s one area where the Cubs have been notably quiet, it’s the bullpen-particularly at the back end. Despite signaling a willingness to spend outside their usual comfort zone, the Cubs have watched a string of high-leverage arms sign elsewhere: Devin Williams, Robert Suarez, Edwin Diaz, Ryan Helsley, Kyle Finnegan, Raisel Iglesias… the list goes on.
That’s why Pete Fairbanks is such a critical name to watch.
The former Rays closer is one of the last remaining top-tier options on the market. He posted a 2.83 ERA and 3.63 FIP last season, and his high-octane stuff makes him a natural fit for a team looking to solidify the ninth inning. The Cubs have been connected to him, but so have a lot of other teams-including the Blue Jays, who’ve been as aggressive as anyone this winter.
Toronto has already shelled out for Dylan Cease and Cody Ponce and are reportedly chasing Kyle Tucker. If they decide Fairbanks is their guy, they’ve shown they’re willing to go the extra mile to get it done.
If the Cubs miss out on Fairbanks, they’ll still have fallback options-Luke Weaver, or perhaps a reunion with Brad Keller-but neither brings the same level of reliability or firepower. At some point, you have to wonder: is the front office truly committed to landing a legitimate closer, or are they just waiting for the price to drop?
Bottom Line
The Cubs didn’t lose ground during the Winter Meetings-but they didn’t gain any either. And with key targets like King, Bregman, and Fairbanks all drawing interest from aggressive suitors, the clock is ticking. This front office has shown patience in the past, but in a market that’s already starting to move, patience could quickly turn into missed opportunity.
The pieces are still there for a successful offseason. But if the Cubs want to keep pace in a competitive NL Central and build on the momentum from 2024, it’s going to take more than waiting for the right deal to fall into their lap.
The Winter Meetings may have been quiet-but the pressure is only getting louder.