Five Bold Predictions for the 2025 MLB Winter Meetings

Today, the baseball world converges on Orlando, Florida, where players, agents, managers, media, and most importantly, front office executives, all come together for the marquee event of the offseason.

The MLB Winter Meetings are a four-day series of events, ranging from the Contemporary Baseball Committee Hall of Fame vote, to the MLB Draft Lottery and the Rule 5 Draft.

Mixed in between, we all hope to get plenty of Passan bombs, with free agent signings and blockbuster trades bound to take place. These next four days are always billed as the pinnacle of the offseason, and yet often we walk away from the meetings a little underwhelmed with the moves that we get.

The free agent cycle in particular has stretched longer in the winter in recent years, with many deals not coming to completion until even after the holiday season entirely. Still, that does not mean that no moves will be made.

In fact, the trade market has been percolating all offseason, and there are sure to be free agents who are heading to Orlando with the intention of coming home with a deal. Which players will move, and which teams will take the big swings?

Let’s dive into some bold predictions on what could take place at this year’s Winter Meetings.

1. Zac Gallen Signs with Anybody But the Cubs

We have seen this story before. A prominent MLB insider attempts to break a story first and runs with bad information in reporting that a deal has taken place. Another reporter weighs in, and cautions that no deal has taken place yet, and the negotiating continues.

Well, when we have seen this happen in the past, there is one thing that always seems to take place next. The player signs with a different team. Arson Judge would be playing right field for the San Francisco Giants if that weren’t the case.

All of this is to say, Zac Gallen can now officially be signed by 29 teams this offseason. The one exception is the Chicago Cubs, who USA Today’s Bob Nightengale reported to have signed Gallen, only for ESPN’s Jeff Passan to refute the report.

Gallen would be a perfect fit for the Cubs. It was actually a prediction that I made that he would sign with Chicago in my article, where I picked a team and projected a contract for every top player in free agency.

The Cubs need another potential frontline starter, and Gallen fits the bill. Bob Nightengale just had to ruin it for everybody.

2. Multiple Big League Starting Pitchers Will Be Traded

If you could be a fly on the wall in the war rooms of your favorite team this week, imagine the ideas you would hear kicked around.

Tarik Skubal, Hunter Greene, and Joe Ryan are all unlikely to be moved in theory, but no GM on the planet has ever stuck both fingers in their ears and refused to listen when an offer is being presented. Teams will be trying to pry top arms, and one is bound to shake loose.

MacKenzie Gore seems like the most likely arm to be traded, as the Nationals are nowhere near contention, and Gore is merely two years away from free agency.

Sandy Alcantara has been in trade rumors for a full calendar year now, and his teammate, Edward Cabrera, has become a constant on the block as well.

Luis Severino would welcome a trade out of Sacramento, and Kodai Senga has been labeled as “extremely available”.

Some trades will take place after the Winter Meetings, but we are going to predict that a few big ones go down over the next few days.

3. Kyle Schwarber Finds a NEW Team

When Buster Olney joined the “Just Baseball Show” yesterday, he described Kyle Schwarber as the linchpin to the market for position players.

Schwarber has been receiving interest around the league, as he brings not only a 56-HR bat, but also the ability to become an instant leader in any clubhouse he walks into. The Phillies are still the favorite to bring him back, but our bold prediction is that Schwarber signs during the Winter Meeting and he signs somewhere new.

Whether that’s a super fun homecoming where we get to see Schwarber play for his childhood team of the Reds, or if the Mets swoop in and steal him from their division rival, leaving open the possibility that Pete Alonso could end up switching places with him in Philly.

4. Edwin Diaz Becomes the Last Man Standing

The one segment of the free agent market that has been moving is the market for top closers. We have already seen Raisel Iglesias, Ryan Helsley, Emilio Pagan, and Devin Williams sign, while Pete Fairbanks, Robert Suarez, and Edwin Diaz all remain on the market, but with plenty of buzz.

With the Dodgers, Blue Jays, and Cubs still needing a closer, and other teams like the Mets, Yankees, Giants, and even Marlins still engaged in those markets as well, there is a good chance we see a few top arms land deals in the coming days.

My prediction, based on what we heard from Olney on yesterday’s Just Baseball Show, is that Edwin Diaz is the last man standing on the market. Waiting out a $100 million deal that may never come.

5. Boras’ Big Bats Remain Unsigned

Every year, Scott Boras finds himself at the center of most of our free agent drama, as he represents some of the game’s biggest stars. This year, Boras’ free agent crop has a lot of familiar faces, as players have opted out of their short-term contracts to once again take a bite at the free agent apple.

Alex Bregman and Pete Alonso each hit free agency for the first time last year, with Bregman landing a heavily deferred three-year, $120 million deal, and Alonso a 1+1 that paid him $30 million in 2025, with a $27 million player option that Alonso declined for 2026.

Cody Bellinger took the second exit ramp on his three-year, $80 million contract he signed after the 2023 season, choosing to opt into his player after after down 2024 season, but now exercising his opt-out after a strong 2025 platform year.

Bregman, Bellinger, and Alonso represent some of the top free agent bats in this year’s class, but it is still unclear if any of them will get the long-term deals they have been after.

With teams trying to gain leverage to pay these star players over shorter terms, my prediction is that negotiations drag out and none of them find deals over the next four days.