MLB offseason reset: 10 biggest questions remaining for the 2026 season after the Winter Meetings

Major League Baseball's Winter Meetings are freshly behind us, and while there was a good bit of notable activity that took place over the three-day hootenanny in Orlando, there's still much to be resolved across the remainder of the offseason calendar. 

That –- what's left for teams to do and free agents to decide –- is now our focus. So let's set the scene for the deeper reaches of winter and the rest of the MLB offseason by exploring 10 questions, the answers to which will shape rosters across the league before spring training and the 2026 season arrive. Onward. 

1. How will the Mets plug their new holes?

You can't sensibly judge an offseason at this relatively early hour, but after the Mets let franchise home run leader Pete Alonso go to the Orioles and All-Star closer Edwin Díaz to the Dodgers those judgments are flying. Now, though, comes the work of replacing the 6.4 combined WAR that just headed out the door. The recent signing of Devin Williams, who's a strong bounceback candidate in 2026, gives them an option at closer, and there's of course plenty of time to turn up additional bullpen depth from the right side. As for first base, they've already had at least cursory discussions with the Cardinals about Willson Contreras' availability in trade, according to MLB.com. He's of course not the only option at that non-premium position. There's plenty of time to address those needs and perhaps fortify the rotation, and it won't be surprising if the Mets are among the more active teams from this point forward.

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2. Will the Orioles address their rotation next?

As just noted above, the O's swung big at the Winter Meetings by adding Alonso's power bat to the lineup on a five-year, $155 million free-agent contract. His addition helps the Baltimore cause in 2026 and beyond, but they still need help in a rotation that's both thin and in want of another frontline presence to accompany Trevor Rogers. Needle-movers like Framber Valdez and Ranger Suárez are still available on the free-agent market right now, and that's to say nothing of the starting pitchers who may or may not be on the trade block (a number of whom play for the Marlins). The implied question, then, is how committed the Orioles are, whether it be in terms of payroll or a willingness to deal prospects, after indulging in half-measures for too long. We'll find out. 

3. Where will Kyle Tucker sign? 

Tucker is our top-ranked free agent for this offseason and, at this writing, he's still available. He's going into his age-29 campaign in 2026, which makes him reasonably young as top-line free agents go, and he's a steady provider of broad-based excellence. For his career, Tucker boasts an OPS+ of 139, and over the last half-decade he's averaged 5.1 WAR per season. In 2025 with the Cubs, he might have wound up firmly in the MVP discussion had a hand injury not sapped his mid-summer production at the plate (he still wound up with a 143 OPS+). Needless to say, Tucker would be a middle-of-the-lineup force for any team. Among those realistic fits are the Dodgers, Blue Jays, Giants, Mets, and Yankees.

4. Will those rumors of a Padres blockbuster come true?

The Padres remain in contending mode, but lead decision-maker A.J. Preller is a bit hamstrung by payroll constraints from the post-Peter Seidler ownership group in San Diego and, when it comes to making trades that improve the current roster, a hollowed-out farm system. Even so, the ever-bold Preller may yet again be aiming high. Let's look back to this tantalizingly vague Winter Meetings nugget from the San Diego Union-Tribune: 

"Two sources familiar with the Padres' discussions said Preller is shooting big.

"One source said the Padres are working multiple fronts that could result in deals that rival the massive trade in which they acquired four major leaguers in exchange for Juan Soto and Trent Grisham at the winter meetings two years ago. Another source said Preller's plans coming to fruition would make the deals he made at the past two trade deadlines pale in comparison.

"The sources, who were not authorized to speak publicly, provided no further details."

Does this mean the Padres are looking to deal away some of their big contracts while navigating no-trade clauses? Or are they looking to finagle another major win-now move despite those aforementioned limitations? Fernando Tatis Jr. has been the subject of recent trade speculation, but multiple recent reports have it that the Padres are committed to keeping the face of the franchise. Could Jackson Merrill be potentially involved in whatever's cooking? That's what MLB.com's Mark Feinsand speculated soon after the above report came out. As return flights from Orlando touch down, the unknowns outweigh the knowns when it comes to Preller's plans. No doubt, though, he has sky-scraping aspirations as the Padres try to wring out another run from their current core. 

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5. Do the Dodgers have another big splash in them?

Even coming off back-to-back World Series titles and with a roster that still includes the superstar likes of Shohei Ohtani, Mookie Betts, Freddie Freeman, and Yoshinobu Yamamoto, the Dodgers aren't letting off the gas. As noted above, they've already landed closer Edwin Díaz on a $69 million pact, and the expectation is that they'll do more in the weeks to come. The Kyle Tucker rumors are out there, and indeed the Dodgers could use an upgrade at one of the outfield corners. They're the most attractive destination in MLB for players, and they have vast resources and -- most critically -- a willingness to use them. The safe assumption is that Andrew Friedman isn't done grabbing headlines this winter. 

6. Will Ketel Marte be dealt?

The Diamondbacks are listening -- "actively listening," in the common parlance of trade rumors -- to offers for stalwart infielder Ketel Marte. They're in need of pitching help and they're seemingly willing to trade one of their best players to get it. Marte's possibly fraying relationship with the team may be playing a role here, but mostly it's about trading from a strength for what the club perceives as a greater need. Marte is 32 and signed through at least 2030 (with a player option for 2031). However, he's signed at bargain rates, and he's coming off a 2025 season in which he amassed a 4.4 WAR in 126 games. Teams in need of a bedrock second baseman are no doubt engaging the Snakes in talks. Will it be the Red Sox? The Blue Jays? The Reds? Someone else? Right now, it seems likely that Marte will be moved, but it could all be complicated by the other second basemen who are the reportedly on the block -- Brendan Donovan of the Cardinals and Brandon Lowe of the Rays. 

7. Will the Yankees reunite with Cody Bellinger?

Bellinger with his 5.1 WAR in 2025 was a big part of the Yankees' regular-season success and their ability to paper over the free agent loss of Juan Soto to the Mets. That means there's a great deal of pressure to bring back Bellinger to the Bronx, at least in the absence of a Tucker signing. Bellinger opted out of his $25 million guarantee for 2026, so he's no doubt looking for a substantial multi-year guarantee. It'll be a serious blow to the Yankees' hopes next season and beyond, especially in the hotly competitive American League East, if Bellinger lands elsewhere. 

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8. Will the Cardinals trade their remaining veterans?

The Cardinals under new lead decision-maker Chaim Bloom are emphasizing the long-term and an ongoing reboot of the club's player-development program. That means trades of veterans for prospect depth, and we've already seen that with the Sonny Gray trade to the Red Sox. He's not going to be the last out of the door. Mentioned above is the possibility that the Mets deal for Contreras (and outfielder Lars Nootbaar). Donovan is Bloom's most valuable trade piece, and the Cardinals have had discussions with multiple teams about his services. As well, the club is working to find a fit for decline-phase Nolan Arenado and his no-trade clause, and lefty reliever JoJo Romero is also probably going to be moved. Will the sell-off grow to include younger talents like Nolan Gorman? That remains to be seen. What's certain is that Bloom and the Cardinals will be making multiple trades of note before the offseason is over. 

9. Will the Cubs do something big?

The Cubs, coming off their first playoff berth in a full season since 2018, should be firmly in buy mode, but the Ricketts continue to refuse to press their substantial financial advantage over the rest of the National League Central. Tucker, to repeat, is almost certain to sign elsewhere. At that point, the central matter becomes replacing his lost value. The Cubs are looking to fortify the rotation and they've also been connected to Alex Bregman. Whatever the specifics, they need to behave aggressively if they're going to surmount the Brewers in the division. 

10. Will the Red Sox bring back Alex Bregman? 

Speaking of Bregman, he was a fulcrum in his lone season in Boston and the Sox very much want to bring him back. They're positioned to contend for years to come with their impressive core of young talent, but they need a veteran known quantity or three to round out the roster. After opting out of his Sox contract, Bregman is no doubt seeking a long-term commitment, and Boston of course has the wherewithal to meet any such demand. There are fallback plans such as a trade for Marte or Donovan, but the most obvious path is a Bregman reunion. 

We'll see if it happens, just as we'll see how all these other questions are answered before pitchers and catchers begin trickling into camps. Much has happened already, but there's even more to come.