10 biggest MLB offseason questions: How bold can the Dodgers go? Will the Tigers trade Tarik Skubal? And more

With the Los Angeles Dodgers freshly crowned as repeat champs, qualifying offers extended or withheld, and free agency upon us, the 2025-26 offseason has begun in earnest. While it will likely be a little while until bigger names start getting traded and putting ink to contract, it's not too soon to start pondering what the winter may hold on the player-movement front. We're here to do just that by posing a series of possibly warm-to-the-touch questions regarding how teams will approach the winter, which players might sign where, and who might get in on a blockbuster trade or two. Come with us, won't you?

1. How will the Dodgers reload for a three-peat bid?

The Dodgers are the best in baseball, not only in terms of winning championships but also when it comes to spending and maneuvering to that end. That's grounds for praise, especially these days. Given all that, the expectation is that president of baseball operations Andrew Friedman will again be aggressive in trying to position his team to win the World Series for a third straight season. The rotation figures to be in good shape -- Yoshinobu Yamamoto, Blake Snell, Tyler Glasnow, and Shohei Ohtani are all still under contract -- with ace quality at multiple spots and depth to spare. Elsewhere, though, the Dodgers could use an upgrade at one of the outfield corners. As such, don't be surprised if they vigorously pursue Kyle Tucker, the top free agent available. The bullpen probably also needs work. If the recent past is any guide, the Dodgers won't be far from the headlines this winter. 

2. Will Bo Bichette be back in Toronto?

One of the biggest questions for the reigning American League champs has already been answered -- veteran right-hander and deadline pickup Shane Bieber exercised his player option and will return to Toronto in 2026. That's welcome news from the Jays' standpoint, but the top priority remains re-upping with shortstop Bo Bichette. Bichette enjoyed an impressive bounce-back season this year after nagging injuries sapped his production in 2024. When healthy, he's one of the best-hitting shortstops in all of baseball, and the Jays need him back. Baseball is ascendant in Toronto right now and losing the popular and homegrown Bichette would not be well received by an engaged fan base. There appears to be mutual interest in a reunion.

Ranking top 50 MLB free agents for 2026: Kyle Tucker, Alex Bregman at top, plus landing spots for every player

R.J. Anderson

3. Will the Yankees make a splash? 

And does it qualify as a splash if all they do is bring back Cody Bellinger and Trent Grisham? To be clear, bringing back that outfielder duo is a laudable goal and something the Yankees should work to make happen absent a major upgrade there (i.e., Tucker). Or do the Yanks in the outfield give regular duty to Jasson Dominguez once again and maybe eye Spencer Jones for an early season callup? They'll get back Gerrit Cole in the rotation, but what about the back of the bullpen? Brian Cashman may need to dip into the free-agent pool for saves. Would he pursue Edwin Díaz and get him to make the crosstown leap? 

4. Will the Phillies reunite with their big two free agents? 

The Phillies are very much in a win-now phase and lead operator Dave Dombrowski has for years been aggressive on that front. Maybe given recent playoff disappointments there's a temptation to give the roster a different look, but that's overlooking all that recent success and over-emphasizing the tiny sample of the postseason. That's why it shouldn't be shocking if the Phillies bring back their two most important free agents -- slugger Kyle Schwarber and front-end lefty Ranger Suárez. Those two in 2025 teamed up for a WAR of 9.4. In what figures to be a tough NL East in 2026, you can't let that kind of value walk without plans to replace it. 

5. Where will Kyle Tucker sign?

No, the 2025-26 class of free agents isn't a particularly strong one overall, but Tucker is a most worthy No. 1. Even when playing through a hand injury cost him at the plate, he still managed to put up an OPS+ of 143 and a WAR of 4.6 in 136 games in 2025. He's still a defensive plus in the outfield corners and he still runs the bases well. Tucker, one of the most complete players in the game, is also still just 28 years of age. It's hard to read this market, but a contract of $400 million or more wouldn't be entirely shocking for Tucker. As noted, the Dodgers make a lot of sense, as do the Yankees, Phillies, Giants, and incumbent Cubs. As always, an unexpected suitor or three will likely emerge at some point. 

6. Will the Tigers trade Tarik Skubal?

To be clear, the Tigers should not trade Skubal. They've made it to Game 5 of the ALDS in each of the last two seasons, and that's not a team that should be trading away the pitcher who's likely to win a second straight Cy Young later this week. That's a contender, and even if it means letting Skubal walk at the end of 2026 for nothing more than a compensatory draft pick, it's worth it just to improve Detroit's odds of hoisting the trophy next year. If lead exec Scott Harris does decide to deal Skubal before his walk year begins, then it'll no doubt be a frenzied bidding. Any team could of course use an ace of aces, but clubs like the Mets, Mariners, and Red Sox are among those who could put together compelling trade packages. The Tigers still have a theoretical shot to sign Skubal to an extension, but they'll have to drastically improve their efforts to date on that front. 

7. What is Chaim Bloom's plan for the Cardinals? 

For the first time since 2006-07, John Mozeliak will not be guiding the Cardinals through the offseason. Mozeliak stepped down from the big chair after this past season and now Chaim Bloom takes over. He inherits a team going through what qualifies as a drought by franchise standards. Trades of veterans like Nolan Arenado and Sonny Gray, provided they waive their no-trade clauses and a fit can be found, are likely, but how much deeper will it go? Will Bloom shop Brendan Donovan, probably his most valuable potential trade piece, or does Bloom see Donovan as part of the next contending Cardinals team? Trades will tell the story of how soon the new front office in St. Louis thinks they can matter again.

8. Will the Twins tear it down (even more)? 

No team sold harder than the Twins did leading up to this year's trade deadline. They may not be done. If the apparent rebuild turns into a full-on teardown, then the Twins might peddle their top two starting pitchers, Pablo Lopez and Joe Ryan. Catcher Ryan Jeffers may be another trade possibility. Star outfielder Byron Buxton says he wants to spend his entire career with the Twins, but what if the shedding of talent continues? Will that change Buxton's mind? An ugly season in Minny could turn into an ugly winter. 

9. Will the Pirates trade Paul Skenes? 

Yes, it's the non-story that won't die. Skenes is excellent and cheap, and that's exactly the kind of player the Pirates cherish. Owner Bob Nutting, an utterly useless figure in a guild overflowing with them, is of course derelict in his duties when it comes to building around Skenes and other young talents. But trading Skenes now, when he's not even arbitration-eligible, makes little sense even from the warped perspective of an owner like Nutting, who has shown no signs he cares about winning baseball games. So, no, they won't trade Skenes this offseason, but the questions will doggedly remain. 

10. Will there be any additional signs of looming labor strife? 

The unfortunate expectation is that next offseason -- the 2026-27 offseason -- will be blighted by an owner-implemented lockout timed to the expiration of the current collective bargaining agreement. The signs are already strong on this front, as commissioner Rob Manfred has tried to spin the likelihood of a lockout as a good thing and has also made comments calculated to drive a wedge between the more tenured members of the MLBPA and the younger players. Talk of a salary cap has also been easy to come by over the past several months, even though the union will never agree to such a thing. We'll probably hear some rumblings on this front coming out of the owners' meetings, which are scheduled for Nov. 18-20. They'll be using the Dodgers repeat as a cudgel, just as they would've been prepared to cite a Brewers win in the NLCS as a meaningless aberration.