MLB’s hot stove is about to get cranked up this week, as the 2025 winter meetings begin Monday in Orlando, Fla., where executives from all 30 teams will gather. And with executives, managers and player agents in the same room, the proverbial engines of the free agent and trade markets are being revved up. Some of the offseason’s biggest deals often go down at the winter meetings. This year could be no different.
The best available position player on the market, Kyle Tucker, met with the reigning American League champion Blue Jays, perhaps a precursor to his market picking up speed this week. Arguably the next best free agent hitter, National League home run king Kyle Schwarber, is a candidate to be the first free agent domino to fall in Orlando. And then there’s the trade market. Will back-to-back AL Cy Young Award winner Tarik Skubal be dealt by the Tigers? All these questions—and more—will be answered in the coming days, making for an exciting time for baseball fans. That said, here are the biggest questions in MLB heading into the winter meetings.
1. Where will Kyle Tucker land?
Tucker, who won’t turn 29 until Jan. 17, combines a 15.8% career strikeout rate and an 11.5% walk rate with 30-home run, 30-stolen base capabilities on offense. And he’s a former Gold Glove winner in the outfield. Put it all together and Tucker is well-positioned to become just the third player in the game’s history to exceed $400 million on a free agent contract.
So where will Tucker, the biggest fish, land? The already-busy Blue Jays, who hosted Tucker at the club’s player development complex in Dunedin, Fla., earlier this week, look poised to be an aggressive suitor for the top free agent bat fresh off of the franchise’s first World Series appearance in 32 years. Contenders with money to spend, such as the Phillies and Giants, should also have a realistic shot at landing the talented outfielder. The Cubs, who traded for Tucker last offseason, aren’t expected to pony up the money to re-sign him.
And while two of the sport’s biggest spenders, the Dodgers and Yankees, may turn their attention to other endeavors rather than splurge on Tucker, they still can’t be ruled out. With a come-one, come-all market, all eyes will be on Tucker in Orlando.
2. Will a top-tier starter get dealt?
The hot stove is already cooking in the starting pitching market, as Dylan Cease, Sports Illustrated’s No. 10 ranked free agent, signed a $210 million deal with Toronto back in November. And we’ve already seen movement on the starter trade market, with former first-round pick Grayson Rodriguez dealt to the Angels, and three-time All Star Sonny Gray and tantalizing 27-year-old Johan Oviedo acquired by the Red Sox.
But there are bigger trades that could be facilitated with the movers and shakers in Orlando. It behooves a playoff contender like Detroit to hold onto back-to-back Cy Young Award winner Tarik Skubal, a 2027 free agent expected to command a record deal, until at least the trade deadline. But if the Tigers are blown away by a monster prospect-laden offer for Skubal, would they pull the trigger and get what they can for the lefty ace now? It bears watching.
Skubal isn’t the only former Cy Young winner who could be moved at the winter meetings, either. Marlins ace Sandy Alcantara, a workhorse starter who was one of the top pitchers available at the 2025 trade deadline before Miami opted to hold onto him, figures to garner plenty of interest from pitcher-needy contenders given that he returned to All-Star form in the second half. If Skubal, Alcantara or another top-tier starter is dealt during the winter meetings, it could shift the hierarchy at the top of baseball’s food chain.
3. Will Kyle Schwarber change teams?
For the third time in the last four offseasons, a league leader in home runs is on the free agent market. In 2022, it was Aaron Judge. In '23, Ohtani. No one would argue that the 32-year-old Schwarber, who is tied alongside Ohtani for the second-most home runs since '22, should command a deal in the stratosphere of the two best baseball players in the world. But it’s likely that the man who just led the NL with 56 homers and finished second in the MVP voting while playing in all 162 games will net a lucrative deal.
The burning question is: Where?
Schwarber has played the last four seasons in Philadelphia, where he has blossomed into one of the very best sluggers in baseball while becoming a fan favorite, as well as a leader in the clubhouse. Since the spring, Phillies president of baseball operations Dave Dombrowski has made clear that he’d like to retain Schwarber—and the mission hasn’t changed come winter.
But Philadelphia will have plenty of competition. The Reds, a dark horse in the race, don’t possess the same coffers that the Phillies do, but might have geography on their side. Schwarber is a native of Middletown, Ohio, which is 35 miles to the north of Cincinnati. Might he be interested in a homecoming with a team on the rise managed by World Series winner Terry Francona? Or could the Mets, sworn NL East enemy of the Phillies, continue their rivalry with Philadelphia into the offseason and push for Schwarber as a Plan B in the event free agent first baseman Pete Alonso leaves? Phillies fans shudder at the thought. Perhaps Schwarber, seeing what the Red Sox are building in Beantown, wants a longer stint in Boston after he helped lead the club to the American League Championship Series as a trade deadline acquisition in 2021. Then, there’s the possibility of a surprise team emerging in the Schwarber sweepstakes.
The hulking slugger perhaps said it best in the aftermath of the Phillies’ gut-wrenching NL Division Series defeat to the Dodgers.
“You never know how it's gonna work out, right?”
4. Which one of Scott Boras’s clients will sign next?
It’s the most wonderful time of the year for commission-gobbling agent Scott Boras, who, in anticipation of the lavish deals he hopes to negotiate, always enters the winter in a jolly mood with punny jokes about his clients not far from his lips.
And Boras has plenty of reasons to be whistling a merry tune heading into the winter meetings. He’s representing four of Sports Illustrated’s top 10 free agents, headlined by Cody Bellinger, Alex Bregman and Pete Alonso, the latter two of whom are the best available at their respective positions. Oh, and Boras also represents two of the more promising free agents from Japan, starter Tatsuya Imai and first baseman/third baseman Kazuma Okamoto.
Plus, for Boras, the festivities have already begun. He helped land Dylan Cease—one of the better starters on the market—the biggest free agent contract in Blue Jays history, kicking the pitching market into high gear in the process.
It’s possible more of Boras’s high-profile clients will net deals in Orlando. The question is, who will be the first? There’s a compelling case that it could be Alonso, whose market seems centered around two big-money contenders—the Mets and Red Sox—with items of equal importance to signing Alonso on their respective to-do lists. Or perhaps Boston bows out of the Alonso sweepstakes and instead quickly ensures that Bregman, a well-rounded third baseman, proven winner and key veteran presence, returns before his market intensifies. There’s also a chance that, should Tucker get signed and set a robust market for position players, that Bellinger—a fine consolation prize for Tucker hopefuls and a Plan A for the wealthy Yankees—finds a landing spot. One thing is for sure: Boras is hoping the winter meetings are quite busy.
5. Could small-market teams make a splash?
The usual suspects are expected to be busy shoppers in Orlando. Most of the teams that comprise baseball’s top 10 payrolls—the Dodgers, Mets, Yankees, Phillies, Blue Jays, Red Sox, etc.—are among the clubs in the mix for some of the sport’s top free agents.
But what about the small-market teams, effectively baseball’s have-nots? Last offseason, the lower-budget Athletics made a free agent splash when the club signed starter Luis Severino to a three-year, $67 million contract that represented the largest guaranteed contract the franchise had ever handed out. There’s a few clubs who could surprise at this year’s winter meetings, similarly to how Oakland did last December.
The Reds, parked amid the bottom 10 teams in payroll, have been linked to Schwarber. Baltimore, possessing a strong, youthful core and an ownership that has been reluctant to spend in offseasons past, is reportedly in the mix for Tucker, as well as top free agent starters Imai, Ranger Suarez and Michael King. The Pirates, mired in a stretch of seven straight losing seasons and owners of one of the lowest payrolls in the majors, have been rumored to be a potential spender with designs on adding to the club’s offense, MLB’s lowest-scoring unit this past season.
Could little-bank-take-big-bank at this year’s winter meetings?
6. How will the Dodgers retool for a run at a three-peat?
Los Angeles became the first team since the 1999 Yankees to repeat as World Series champions. Those Yankees went on to capture a third championship in 2000. Can the Dodgers enter truly rarified air in '26? To do so, they will need to address one of the club’s biggest weaknesses: the bullpen. Dodgers manager Dave Roberts, knowing where his bread was buttered—and wasn’t—largely rode his starters to the Dodgers’ second straight title, as they averaged nearly six innings pitched per start in the postseason. And after the Dodgers’ bullpen posted an ERA north of four and the seventh-most blown saves during the regular season, one would expect the club to address the bullpen this winter.
But could the events of last year’s offseason dissuade Dodgers’ brass from opening up the wallet to spend on relievers? Los Angeles inked relief pitchers Tanner Scott and Kirby Yates to deals for a combined $85 million, but the two underachieved mightily. Thus far, the Dodgers have reportedly been circling the waters around three-time All-Star reliever Edwin Diaz, but perhaps the market accelerates to heights too rich even for the affluent Dodgers. Improving the bullpen on the margins is not out of the question for Los Angeles.
The Dodgers also have a need in the outfield, given Michael Conforto’s free agency, as well as the inconsistencies of Teoscar Hernández and Andy Pages. Might Los Angeles make a splash by landing the top free agent in Tucker or perhaps seek a reunion with Bellinger, who rose to MVP heights and won a World Series during his six seasons with the club? The Dodgers could also explore the trade market for some upgrades in both the bullpen and outfield.
Whether the back-to-back defending champions choose to reload loudly or quietly makes them a potential catalyst in Orlando.
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This article was originally published on www.si.com as The Six Biggest Questions Entering MLB Winter Meetings.
