Writing the Script for Epic 2025 MLB Winter Meetings with FA Signings, Trades, More
The winter meetings are here, and that is supposed to mean a flurry of signings and trades that remake the landscape of Major League Baseball. As such, it would be a bummer if anyone rained on the parade before it even got going.
"I think it's going to be a boring winter meetings," one veteran general manager told Bob Nightengale of USA Today. "I just can't see much happening after talking to teams this past week."
Well, shoot. It looks like we'll just have to imagine what a truly epic winter meetings would look like.
Ahead is an eight-part script for signings and trades that would turn Orlando, Florida into a veritable factory of MLB headlines. This is about creating the highest possible drama, with major actions producing equal and opposite reactions—yet all while staying within the realm of possibility, of course.
Let's begin with a signing that is frankly overdue in the Windy City.
The Cubs Finally Get Alex Bregman
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Why It Would Be Cool
If any Cubs fans are still holding out hope the team will re-sign Kyle Tucker, we have a job for you: Grab that shovel in the corner and dig a hole for those hopes.
According to Patrick Mooney and Shahadev Sharma of The Athletic, the Cubs are preparing for Tucker's exit from the North Side. They're instead preparing runway for rookie hitters Owen Caissie and Moisés Ballesteros, the former of whom can fill Tucker's shoes in right field.
Now, Alex Bregman, on the other hand, is a former Houston Astros great who's actually in play for the Cubs.
The 31-year-old has been one of the game's top offensive third basemen for a long time, averaging a .846 OPS and 28 home runs per 162 games since his debut in 2016. He's perfect for a hot corner spot that produced a .621 OPS in 2025, the second-lowest of any team.
As the Boston Red Sox well know, Bregman is also a great guy to have in the clubhouse. In fact, it was apparent even earlier this year that he would be welcomed with open arms if he did make his way to Wrigley Field.
Why It's Realistic
The Cubs came close to signing Bregman last winter, offering him a four-year, $115 million contract that was just $5 million leaner than the one he accepted from Boston.
Evidently, the experience of having been spurned hasn't left any hard feelings in the Cubs' front office. Per the report from Mooney and Sharma referenced above, they are showing "renewed interest" in the three-time All-Star this winter.
The Red Sox Grab Ketel Marte from Arizona
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Why It Would Be Cool
If it's the Cubs that end up signing Alex Bregman, suddenly the Red Sox are going to be without an obvious solution to a major hole on their infield.
Luckily, they have an opportunity to trade for one of the best infielders in the game today: Ketel Marte.
The 32-year-old has produced 16.0 rWAR over the last three seasons, good for eighth among all infielders and sixth among middle infielders. He's a very good defender whose offensive baseline for the last two seasons has been a .913 OPS and 32 home runs.
The Red Sox began this year hoping Kristian Campbell would finally put a stop to a revolving door at the keystone. Instead, he now finds himself in limbo after he flopped and Boston used six different players at second base.
Granted, Marte doesn't have Bregman's reputation as a clubhouse leader. All the same, the Red Sox would be getting a significant on-field upgrade, which is what they really need if they're going to go win the AL East for the first time since 2018.
Why It's Realistic
According to Bob Nightengale of USA Today, Marte is the "biggest star who is a realistic candidate to be traded," and the Red Sox are one of the teams that have checked in.
Between his talent and the fact that he's owed just $91 million over the next five seasons, the Arizona Diamondbacks can put a huge price tag on Marte. The Red Sox have surpluses of what they need, though, namely outfielders and pitching.
The Reds Bring Kyle Schwarber Home
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Why It Would Be Cool
Kyle Schwarber is another slugger the Red Sox have been linked to, but he won't be up a certain creek without a paddle if they look elsewhere for a bat.
Hot off a four-year run with the Philadelphia Phillies in which he launched 187 home runs, it seems like everyone wants a piece of the 32-year-old. The Phillies have felt like the favorites all along, but what if he gets a fair offer to go home?
He's from the Cincinnati area, and the Reds have already demonstrated a willingness to tug at his fondness for his hometown. And with their offense coming off a season in which it was merely average at scoring runs, now is the perfect time to do so again.
He would slot nicely into a designated hitter spot that didn't do much designated hitting in 2025. Its .721 OPS was in the bottom 10 of MLB, whereas Schwarber posted exactly a .928 OPS for the second time in the last five seasons.
While Schwarber doesn't exactly need help to hit home runs, he's likely well aware that Great American Ball Park is one of MLB's great launching pads. Per Statcast, it's even friendlier to home run hitters than Citizens Bank Park.
Why It's Realistic
The Reds have never spent more than $64 million on a free agent. They might have to clear that by $100 million to sign Schwarber, which feels like a lot to ask of them.
And yet, Ken Rosenthal of The Athletic gave Reds fans hope on December 3. Not only are the Reds serious about signing Schwarber, according to his report, but the player himself is "interested in a possible homecoming."
The Phillies Replace Kyle Schwarber with Cody Bellinger
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Why It Would Be Cool
So, Phillies. You just lost Kyle Schwarber. Are you going to take that lying down?
Of course they wouldn't. If anything, the positive spin on Schwarber leaving is that it would make it easier for president of baseball operations Dave Dombrowski to shake up a roster that clearly needs changes.
Which brings us to Cody Bellinger. He isn't going to hit 50-plus home runs, but he could hit 20-30 for the Phillies and otherwise bring things they badly need: versatility and a good glove.
Bellinger logged at least 300 innings in all three outfield spots for the New York Yankees this year, and he posted a plus-12 Defensive Runs Saved in doing so. The entire Phillies outfield was at minus-16 for the season.
After exploiting Yankee Stadium for a .909 OPS and 18 of his 29 home runs, he could be reasonably confident Citizens Bank Park would treat him just as kindly. Per Statcast, it's even better than Yankee Stadium for left-handed power hitters.
Why It's Realistic
It's safe to assume that if the Phillies lose Schwarber, money won't be the reason why. They can afford him, and they therefore can afford Bellinger, who might even be in line for a smaller guarantee.
As for whether the Phillies are even interested in the 30-year-old former MVP, Jeff Passan of ESPN says the answer is yes.
The Yankees Get Their Man in Tatsuya Imai
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Why It Would Be Cool
There's been a ton of noise about the Yankees wanting to bring back Cody Bellinger, but the situation got complicated when Trent Grisham accepted his qualifying offer.
The Yankees now have Grisham and Aaron Judge set for center field and right field, respectively. They could sign Bellinger to mainly play left field, but that would mean blocking Jasson Domínguez and Spencer Jones from playing time.
Instead, the Yankees might as well take whatever money they have set aside for Bellinger and go all-in on Tatsuya Imai.
Armed with as many as four above-average pitches, the 27-year-old right-hander would bring still more excellent stuff to a rotation that is already set to have Max Fried and Cam Schlittler at the outset of 2026, with Gerrit Cole and Carlos Rodón standing by to return from elbow surgeries.
Plus, the Yankees still owe the Los Angeles Dodgers payback for 2024. Their ears must have perked up, then, when they heard Imai would rather beat the Dodgers than join them.
Why It's Realistic
The Yankees have looked like a fit for Imai for a while now, and MLB.com's Mark Feinsand reported they are "believed" to be one of the most interested clubs in the righty.
They're not alone in this regard, but outbidding the Yankees for someone they want is always easier said than done.
Kyle Tucker Becomes the Blue Jays' Next Star
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Why It Would Be Cool
The Yankees are, of course, playing catchup to a Toronto Blue Jays squad that beat them in the AL East race and in the ALDS, and which already has a leg up this winter after $240 million worth of deals for Dylan Cease and Cody Ponce.
Now all they need is Kyle Tucker, right?
"Need" might be putting it too strongly, given their offense ranked fourth in scoring this season. But then again, said offense is missing Bo Bichette, and it could use at least one upgrade in the outfield.
To this end, it's hard to do better than the best position player on the market. Even though a fractured hand left him cold for much of 2025, the 28-year-old Tucker did better than a 140 OPS-plus for the third straight season, also crossing 20 homers and 20 stolen bases for the third time in the last four.
The Blue Jays already have Vladimir Guerrero Jr. signed for the next 14 years. If they also do a long-term deal with Tucker, they could look forward to having the AL's best offensive tandem for the next decade.
Why It's Realistic
Though the Blue Jays have already spent a ton of money, they're still a clear fit for Tucker. They've been consistently linked to him all winter, and Robert Murray of FanSided reported the team recently hosted him in Florida.
It could cost as much as $400 million to secure Tucker's services. But that's nothing the Blue Jays can't afford, and they seem all-in on avenging their heartbreak in the World Series.
The Blue Jays Also Reel in Edwin Díaz
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Why It Would Be Cool
The Blue Jays had it. Seriously, they had it. With a one-run lead and two outs in Game 7 of the World Series, they had a 91 percent chance of winning.
That Jeff Hoffman blew it by allowing that game-tying homer to Miguel Rojas was only surprising because of the Miguel Rojas of it all. Hoffman had been homer-prone all year, giving up 15 long balls in 68 innings.
The lesson, clearly, is that the Blue Jays can and should want a less volatile option for the ninth inning. And it's simple: Edwin Díaz is the best they or anyone else can do.
The righty has been in the league for nine years, and he's posted sub-2.00 ERAs in four of them. That includes this year, for which his 1.63 ERA and 4.7 strikeout-to-walk ratio made for an easy decision to opt out of his contract.
Because he'll be 32 on March 22, there is some question as to how long Díaz can keep this up. But if he can do it for even one more year, whatever contract the Blue Jays give him will have paid off if he gets the two outs they couldn't get this year.
Why It's Realistic
The Blue Jays appear to be a possibility for Díaz, according to Ken Rosenthal of The Athletic. But if they follow their nine-figure deal with Dylan Cease with another for Kyle Tucker, could they really afford to sign Díaz to a nine-figure deal as well?
It might be a reach. But then again, the Blue Jays have the Canadian market all to themselves and they're riding higher than they have been in a long time. They're as good a candidate as anyone to lead MLB in offseason spending.
The Mets Pull off a Tarik Skubal Blockbuster
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Why It Would Be Cool
Having already signed Devin Williams, the New York Mets can lose Edwin Díaz and be none the worse for wear. Indeed, what they really need is starting pitching.
Which brings us to a fun statistical comparison:
If anything, it might be a surprise that Skubal wasn't more valuable than the entire Mets rotation. He somehow got even better after his Cy Young Award-winning season in 2024, lowering his ERA while pitching more innings and raising his strikeout-to-walk ratio.
He is flatly ridiculous, alright, and he's certainly the best possible upgrade the Mets can make to their starting rotation this winter. He'd also give them a sort of superstar balance, as the Mets need a proper No. 1 to support Juan Soto and Francisco Lindor on the offensive side.
Why It's Realistic
The Tigers "continue to be engaged" with other teams on Skubal, according to ESPN's Buster Olney. And despite buzz that has mostly been to the contrary, he also heard from one rival executive that the Detroit Tigers are likely to trade him.
Even with just one year remaining between him and free agency, the 29-year-old is loaded with trade value. The Mets, though, have young pitching to offer the Tigers, including Nolan McLean and Jonah Tong.
Ideally, Skubal would stay in Queens for longer than just one year. Yet even if they can't extend him, trading for him would give them a valuable head start on courting him in preparation for a potential $400 million contract.
Stats courtesy of Baseball Reference, FanGraphs and Baseball Savant.
