The MLB calendar waits for no one. Sure, you might still be decompressing from an all-time classic of a World Series between the Dodgers and Blue Jays, but free agency is right around the corner. A very busy offseason has already begun as teams and players make option decisions and get their houses in order. Pretty soon, GM and Winter Meetings will be here, and Hot Stove season will be in full swing.
This figures to be a fascinating offseason, both because of how many teams might plausibly contend in 2026 and also because of the wide variety of players available either in free agency or trade. So let's try to take the lay of the land but asking some hard questions — specifically, the biggest offseason question for all 30 teams. Some focus on one specific position of need. Others are more existential. But all of them will help define this winter, and set us on the path to determining who's winning it all next October.
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AL East
Baltimore Orioles: Are the O's open to moving Adley Rutschman?
Unless and until I see Mike Elias actually do it, I refuse to believe that he's willing to spend big money in free agency. So the best chance Baltimore has of finding the rotation help it desperately needs is via trade ... which brings us to Rutschman, who has two years of team control remaining and is being pushed by top prospect Samuel Basallo. He's also coming off back-to-back subpar years, at least in part due to injury. Are the O's willing to cut bait, and how much would the rest of the league be willing to spend?
Boston Red Sox: Can we please get Garrett Crochet some help?
It's not the only question to answer — which outfielder gets traded and is a run at Pete Alonso in the cards? — but it is the biggest one. Boston can't be wholly reliant on Garrett Crochet to carry this rotation again in 2026. He needs some help, and there just so happen to be a ton of starters potentially available via trade. Which one does Craig Breslow think most highly of? Sandy Alcantara, maybe, or Joe Ryan, or Hunter Greene? And what will it take to get a deal done?
New York Yankees: Kyle Tucker or Cody Bellinger?
Let's keep this simple. New York needs to rebuild its outfield with Bellinger and Trent Grisham hitting free agency. And because these are the Yankees we're talking about, you know they're going to pay somebody. But will that somebody be Bellinger, who was an excellent two-way player in 2025? Or will Brian Cashman (and Hal Steinbrenner) be willing to go big to add Tucker's superior bat? If they want to finally get over the hump in October, they probably should be.
Tampa Bay Rays: Will a Brandon Lowe trade materialize?
The Rays are never major players in free agency, and they're always looking to flip expiring contracts into controllable talent. Enter Lowe, who has a team option worth $11.5 million for 2026. Tampa will almost certainly pick that up, not to keep the slugging infielder, but so that they can trade him somewhere else. In a market thin on impact infielders, Lowe's power and reasonable price tag should make him a valued commodity. Can the Rays get a return that will help them stay afloat in the AL East?
Toronto Blue Jays: Will Bo Bichette stick around?
Pitching is the biggest need of the winter for Toronto, though keeping Shane Bieber around helps a whole lot there. But the biggest question mark has to be Bichette, one of the best hitters on the market this winter and the only one who plays an up-the-middle position (though he really should slide over to second soon). Bring him back, and another World Series run is right in front of them. If he leaves, though, they might have a tough time replacing his production, not to mention his stature in Toronto.
AL Central
Chicago White Sox: Can we finally end the Luis Robert Jr. saga?
Please, Chris Getz, I'm begging you: I'm so tired of having to speculate about what a Robert Jr. trade might look like. Chicago has been dancing around its mercurial outfielder for years now, but this winter feels like an inflection point. The White Sox just picked up the first of two straight $20 million team options for 2026 and 2027, meaning the clock is officially ticking before he hits free agency in 2027. Getz clearly wants to wait until he can sell high, but that possibility seems more and more remote. Time to pull the trigger and move on.
Cleveland Guardians: How serious is this ownership group?
The Guardians defied gravity to steal the AL Central from Detroit, but their loss in the Wild Card round revealed just how far away this team really is from contention. And they'll remain that way so long as they run payrolls at or near the bottom of the sport. Get a bat or two around Jose Ramirez, and this pitching staff could make some serious noise. But they'll need to defy recent history to do so: The largest free-agent contract the club has ever handed out was Edwin Encarnacion's three-year, $60 million deal way back in 2017.
Detroit Tigers: Tarik Skubal. That's it, that's the tweet.
Could it be anything else? The Tigers are nearly at a point of no return with their Cy Young winner; it's time to either get serious about a contract extension or get serious about trading him. To be perfectly clear: This should not be a difficult choice. And yet, it's become one, and it doesn't seem like Scott Harris and/or owner Chris Ilitch are willing to pay what's necessary to keep Skubal around for the long haul. If they can't get a deal done, how willing will they be to carry the lefty into the regular season, just months before he hits free agency?
Kansas City Royals: Can someone please help this outfield?
No, seriously, please. Kansas City's outfield wasn't just punchless last season; it was by far the most punchless in baseball, with a 70 wRC+ that ranked last in the league by a full 10 points. The Royals have pitching depth and an MVP candidate in Bobby Witt Jr. But none of it will matter unless they can put more help around him and Vinnie Pasquantino in this lineup. It starts with attacking the outfield aggressively, either via free agency or trade. (Jarren Duran, anyone?)
Minnesota Twins: How much can you get for Joe Ryan (or Pablo Lopez)?
The Twins are clearly uninterested in fielding a legitimate Major League Baseball team in 2026. So instead, we'll focus on which big names will be next to flee Minnesota. Ryan is the more frequently discussed trade target, but Lopez also has just two years remaining on his deal; neither will be a member of the next competitive Twins team, which means either (or both) could go this winter while they still have multiple years of team control remaining. Lopez's injury-plagued 2025 might dampen his market, though, so it's likely that Ryan goes first.
AL West
Athletics: Will John Fisher finally find some money?
The A's are closer to relevance than you might expect. They won 76 games last year, and they finished 10th in team wRC+, with several rising young stars like Jacob Wilson, Nick Kurtz, Tyler Soderstrom, Shea Langeliers and Lawrence Butler anchoring the lineup for years to come. This team is just a couple of pitchers away ... but therein lies the problem. Is Fisher willing to put money into this team while it languishes in Sacramento? And will anyone be willing to take that money to come pitch in a Minor League park?
Houston Astros: Where are the innings going to come from?
Offense was the main reason Houston missed the playoffs this season, but the rotation is the biggest question mark here. Only two pitchers threw more than 100 innings for this team in 2025, and one of them, Framber Valdez, is almost certainly gone in free agency. Sure, Cristian Javier's return should help, and Hunter Brown is great, but just about everybody else is either hurt or unproven or both. The Astros are going to need to really get creative here to field a functional starting staff that can survive 162 games.
Los Angeles Angels: Is Arte Moreno capable of facing reality?
For the first time in a long time, signs might be pointing to yes: According to Jon Morosi, the Halos are open to moving veteran outfielders Jo Adell and Taylor Ward, an indication that this franchise has finally realized that it's in desperate need of a reset. Bottoming out is almost certainly out of the question as long as Moreno's still in charge, but will anyone else be on the move? And can the Angels finally stop handing out at least one baffling free agent deal per winter?
Seattle Mariners: Was Jerry Dipoto's aggression a one-time deal?
The Mariners have arrived, and with a lights-out rotation, Julio Rodriguez and Cal Raleigh in tow, they shouldn't be going anywhere. But with Josh Naylor and Eugenio Suarez set to hit free agency, there are some questions that need to be answered offensively. And until this past trade deadline, Dipoto hadn't shown much of any willingness to get outside of his comfort zone. Will he get aggressive on the heels of an ALCS run? Or will he continue to keep his powder dry and fiddle on the margins? A reunion with Naylor, in particular, feels like a must, but someone like Kyle Schwarber would be a lot of fun.
Texas Rangers: How much money will Chris Young have to spend?
Word out of Texas is that ownership is demanding a decrease in payroll next year, after the seventh-most expensive roster in baseball hardly sniffed a playoff spot in 2025. It remains to be seen, though, whether that decrease will be more of a trim or a full-on buzzcut. There's still a solid core here, but at least one bat and plenty of pitching depth is needed. Can Young do all of that on a budget?
NL East
Atlanta Braves: What's the plan at shortstop?
More pitching depth is needed to guard against injury, but Atlanta knows who its horses will be. And just about every position on the diamond is spoken for in 2026 ... save for shortstop, now that Ha-Seong Kim has chosen to opt out of his deal and hit free agency. Will a reunion be in the cards after Kim gave the Braves a much-needed jolt late in the year? Or will Alex Anthopoulos use some of last year's savings to make a run at someone like Bichette? The pieces are in place for a real run, but it'll require a bigger offseason than we got last winter.
Miami Marlins: How likely is a Sandy Alcantara trade?
The Marlins don't need to deal Alcantara; he's still got one more club option in 2027 at $21 million before he hits free agency. But this is a quietly ascending team, and Alcantara's strong second half may have rebuilt his value enough to the point where Miami is able to sell high with two more years of team control remaining. Flipping Alcantara for multiple cost-controlled pieces would be a very Marlins move, and if they hit a home run there, this group could make noise sooner rather than later. He's the one big chip they have left to play, as long as Edward Cabrera remains off the table.
New York Mets: Is David Stearns willing to get uncomfortable?
David Stearns has had time to set the table. Now, after a historic late-season collapse, it's time to go hard. But it's unclear whether Stearns has that in his DNA. If he wants to bring back Edwin Diaz, he's going to have to get uncomfortable. If he wants to go get an ace, he's going to have to get uncomfortable. Eventually, you have to stop being the most rational guy in the room and go get the players you need, and it feels like the Mets have reached that point as they attempt to maximize Juan Soto's prime. We'll see if Stearns has a little crazy in him after cutting his teeth in smaller markets.
Philadelphia Phillies: Which free agents stay (and which ones go)?
The Phillies are desperately trying to keep this core together long enough for one more real run at a World Series title. The problem is that, after two straight NLDS defeats, it's threatening to come apart at the seams: Kyle Schwarber, Ranger Suarez and JT Realmuto are all off to free agency, not to mention role players like Harrison Bader and Max Kepler. How much money will Dave Dombrowski have to work with, and who will he prioritize? Can he keep both Schwarber and Suarez? The former feels like the most critical piece, but the bidding will be intense. And if this offseason gets away from Philly, the whole foundation might collapse.
Washington Nationals: How close does this new front office think the Nats are?
The Nats find themselves at a bit of a crossroads, hopefully closer to the end than the beginning of their rebuild but still very far from meaningful contention. Paul Toboni arrives from the Red Sox to run this front office, but what will he make of the group he inherits? If he likes what he sees, he could put his foot on the gas and try to build around James Wood, CJ Abrams and MacKenzie Gore. If not, maybe he pivots and tries to remake this roster in his image, starting with a trade of Gore.
NL Central
Chicago Cubs: Will it be more of the same (derogatory) from Jed Hoyer?
It didn't take long for Chicago to crush fans' dreams. A run at keeping Kyle Tucker around? Not happening. A long-awaited bullpen splash? No way. This is a Jed Hoyer team, after all, and despite disappointing returns of late, Hoyer refuses to change his stripes. He's never going to compromise future flexibility, and with Tom Ricketts controlling the purse strings, this team feels like it's never going to fully flex its muscles on the open market. Which is fine enough: The Cubs have a ton of talent and more on the way from their farm system. But if the bar is the Dodgers ... well, good luck.
Cincinnati Reds: How much is Cincy willing to spend on a bat?
The Reds' pitching is ready to win, so long as they keep Hunter Greene, Andrew Abbott, Nick Lodolo, Brady Singer and Chase Burns together. The offense, though, needs some work, and it remains to be seen whether Reds ownership is willing to pay to get that work done. Hometown hero Kyle Schwarber would fit this lineup like a glove; then again, he'll also cost more than this front office has ever shown a willingness to pay. Will that change, or will this competitive window go by the wayside?
Milwaukee Brewers: Who will be in this rotation come spring?
Milwaukee has young, cost-controlled talent at just about every position on the diamond. The rotation is another question, with Brandon Woodruff declining his player option and Freddy Peralta a potential trade candidate with one year of team control remaining. Both have been instrumental to this team's success, but will either of them be back in 2026? And if they're not, how does a team of limited means backfill their spots and build a starting five around Jacob Misiorowski?
Pittsburgh Pirates: Is Bob Nutting serious?
We could talk about Pittsburgh as a baseball team in 2026, one that could be pretty good with a rotation built around Paul Skenes, Mitch Keller, Bubba Chandler, Jared Jones and more. But really, what would the point of that be? These are the Pirates, after all, and as long as they remain under the ownership of Nutting, none of the rest matters. Pittsburgh is a functional offense away from Wild Card contention; that would require going out and buying a bat or two, though, and that's simply beyond the pale for some reason. Don't worry, we'll have a salary cap soon enough.
St. Louis Cardinals: Which veterans will be on the move?
The rebuild is well and truly on in St. Louis, as Chaim Bloom takes over for John Mozeliak and sets about shedding dead weight and getting this team younger and cheaper. But while it's all too easy to say that the Cardinals should move on from the likes of Nolan Arenado, Sonny Gray and even Willson Contreras, actually doing so could prove tricky. It takes two to tango, after all, and good luck finding a team willing to take on hefty contracts for declining players well into their 30s. St. Louis might wind up having to eat some money to facilitate a deal.
NL West
Arizona Diamondbacks: Is this team contending or not?
The Diamondbacks find themselves in a bit of limbo this offseason. There's too much talent to well and truly bottom out, but Zac Gallen and Merrill Kelly have moved on and Corbin Burnes may not pitch at all in 2026 as he rehabs from Tommy John. So where does that leave Arizona? Are they looking to still make a run at a Wild Card spot next season, with an offense built around Corbin Carroll, Ketel Marte and Geraldo Perdomo? Or is this a bit of a reset, a time to reset payroll and give the young guys some rope and come back in 2027 ready to rock?
Colorado Rockies: Can we take one (1) step toward normalcy?
It wouldn't be worth anyone's time to talk about the Rockies' prospects in 2026. Really, the only question here is a far more existential one: Can Colorado become a normal, functioning MLB organization? So far, the answer has been no, and as their search for a new head of baseball ops lingers on, it doesn't seem like that will change any time soon. The Rockies need new blood desperately, an actual baseball executive who can run this like an actual baseball organization. If they find a way to do that, this year will be a success by default.
Los Angeles Dodgers: How will Andrew Friedman rebuild this bullpen?
The Dodgers might make a run at someone like Tucker, but I'm skeptical given how cool they were on the Soto sweepstakes last winter. The real pressing need for the two-time defending champs is fixing a bullpen that nearly tanked their repeat bid this season. The Tanner Scott deal has already turned into a disaster, and with Roki Sasaki moving back into the rotation, the Dodgers need a back-end option (or two) to take his place. Edwin Diaz? Robert Suarez? Raisel Iglesias? Devin Williams? The choices are almost endless.
San Diego Padres: Is AJ Preller out of ammunition?
The clock might be about to strike midnight on the Preller era in San Diego. His go-for-broke approach to the trade deadline broke very, very badly, and now Yu Darvish is out for 2026 while Dylan Cease and Michael King are off to free agency. The rotation, as it currently stands, is Nick Pivetta, a returning Joe Musgrove and a bunch of question marks. The offense has some big names but finished 28th in homers last season. The arrow is pointed in the wrong direction, and the cupboard is getting bare both financially and in terms of prospect capital. It's tough to see how Preller might turn this around, if he even gets the chance to.
San Francisco Giants: Can Buster Posey land his biggest fish yet?
Say this for Posey: He's not content with the status quo. He inherited a Giants team that had been unable to land a star for years, then promptly signed Willy Adames and traded for Rafael Devers. But the results on the field haven't been there quite yet, and Posey appears to be getting more and more desperate. Which makes this offseason so intriguing: On paper, San Francisco feels like a great fit as a Kyle Tucker landing spot, with a hole in right field and money to burn and a desire to win right away. Can this be the year they finally seal the deal on a legitimate superstar free agent? And will that be enough to scare the Dodgers?