At this point, Major League Baseball’s winter merry-go-round of blue chip free agents should be slowing to a halt. Yet here we are, a week before the holidays tip off in earnest, and the music has hardly commenced.
Generally, if business isn’t finished by Dec. 25, it gets booted into the new year, where a different countdown clock commences: a month or less before the modern player typically arrives at their team’s spring training facility.
And it’s not so much the big names still on the board as it is the lack of specificity attached to them. Certainly, tires have been kicked and perhaps even offers made under the radar, but since a brief winter meetings burst, movement has been anything but imminent.
With that, let’s aim to speed things along with destinations for a half-dozen of this winter’s biggest names:
Kyle Tucker
Might be the quietest and oddest pursuit of a definitive 1/1 free agent in recent memory – heavy on supposition, light on specifics. Lest we remind you, Juan Soto and Shohei Ohtani signed their $700 million-plus contracts just as the winter meetings began and shortly after they concluded, respectively, the past two seasons.
Even in the grim soft core collusion days of recent vintage, there were sightings of Manny Machado sneaking a meeting at Citizens Bank Park and rumblings that clubs might try a quick strike on Bryce Harper on a shorter term, fatter annual basis before those fellows found homes nearly a month into spring training.
Tucker? He’s a bit less dynamic a presence than the aforementioned superstars, and thus the buzz has been a tad less palpable. But his time will come soon, as the pool gets shallower.
And the destination that’s made sense all along – Toronto – only continues to blink brightly.
The Blue Jays’ podium finishes in the Soto and Ohtani sweepstakes shows a fair amount of dry powder remains at Rogers Centre even after they inked their own franchise player to a $500 million deal. Sliding Tucker into a corner outfield spot would also come so easily and provide a readymade lineup replacement when George Springer departs after this season.
But for 2026, the Blue Jays can pretty much concoct a dream team, with fresh blood to quickly cure that one-game-short residual effect as they gun for a World Series title.
Destination: Blue Jays
Bo Bichette
Yeah, might as well get both these guys out of the way. It’s a bit less likely the Jays can lay out cash for Vladimir Guerrero Jr. and Dylan Cease and Tucker and retain their homegrown middle infielder, who recently reportedly acknowledged he’d be willing to move off shortstop to second base.
That will significantly boost the comfort level for prospective suitors who might have been scared off by his suboptimal defensive metrics as he reached his late 20s. And while his market value may take a little hit, his offensive profile – two-time AL hits king, consistent 20-plus home run pop, a .311 average and .840 OPS in his platform year – holds up quite well at second.
Yet will the market be there for him in this particular winter?
Teams certainly loved what they saw in 2025, and even after a knee injury cost him the final month of the season and the first two rounds of the playoffs, his relatively heroic World Series performance on essentially one leg was an eye-opener.
Still, he may find the landscape more lucrative next winter, with another big offensive year on the board and 162 games to show how dynamic and productive he can be at second base. More teams should be in play: Nico Hoerner and Jazz Chisholm Jr. will be free agents, which on one hand fills the market with second basemen but on the other puts a pair of massive-market teams in the mix.
Perhaps Bichette follows the path old teammate Marcus Semien paved: A switch to second, one massive season in Toronto and then a return trip to the market a year later, when he’ll still be just 28.
Destination: Blue Jays
Framber Valdez
We certainly miscalculated, believing Valdez might be a 1A to Dylan Cease’s No. 1, if not a tad higher given Valdez’s uber-consistent success in Houston.
Alas, chicks – and by chicks, we mean front offices – dig the strikeout, which is why the Blue Jays lavished $210 million on Cease before the turkey hit the oven last month. Valdez is simply a horse whose value spreads intrinsically throughout a five-man rotation.
He’s averaged 192 innings for the Astros the past four seasons, toting a 1.16 WHIP all along, has won some huge playoff games and consistently punches out eight to nine per nine innings over his career.
Sure, his Texit wasn’t entirely smooth, and he’s not the sort of ace whose charisma might light up the box office. But the Baltimore Orioles don’t need that: They’ve got Pete Alonso and the proverbial bright young core, and are badly in need of both pitching and a guy who can predictably provide more than 150 innings of excellent work.
The Orioles said they had no limitations financially this winter, and we believed them, and suddenly Alonso was studying up on how best to crack a crab. They intimated they weren’t done this winter even with Alonso in the fold.
We still believe them.
Destination: Orioles
Alex Bregman
When you put on the Boston Red Sox uniform, the window between beloved superstar and whisper campaign once you leave is never large. And by all metrics, Bregman’s one year in Boston – on a heavily-deferred $40 million salary with an opt-out – was a huge success.
The consummate clubhouse dude played a massive role in returning playoff baseball to Boston, even if his arrival created a domino effect that shoved Rafael Devers off third base and eventually to San Francisco.
Yet with roughly $250 million off the books thanks to Devers’ departure, re-upping Bregman should theoretically be easy enough – along with further upgrades. But the Red Sox passed on Alonso and Bregman is hanging out there like a massive prize, posting grindset thirst traps from his Arizona gym, even as the local team out there put up smoke signals it might be in on him.
It all adds up to a classic Boston ghosting, even as Fenway Sports Group projects to pocket nearly $1 billion from its reported sale of the Pittsburgh Penguins. Hey, sustainability should be just around the corner.
Meanwhile, all the old characters are back in play from Bregman’s first go-round in free agency. And at Wrigley Field, they’ll be losing Tucker’s big bat – and hefty salary – to free agency.
Even as Matt Shaw showed some viability in his rookie season, there’s still plenty of room for Bregman, whose 128 adjusted OPS would be a massive upgrade over Shaw’s 98. Hoerner’s potential departure would allow room for both on the dirt in 2027.
And should Bregman land on the IL a couple times, as he did with the Red Sox, there’s admirable depth to cover for him. Besides, the Cubs could use another dawg.
Destination: Cubs
Cody Bellinger
This might be the ultimate staring contest of the winter, the Yankees certainly wanting their very valuable corner outfielder back, Bellinger perhaps desiring a few more years of financial certainty than the Yankees are willing to offer.
It’s a tricky spot, to be sure, given Bellinger’s age (30) and that his 152 games played marked just the second time since 2019 he’s topped the 130 mark.
But he’s clearly healthier than he’s been since he was the NL’s 2019 MVP, and worthy of an extensive, but not crazy, commitment.
And that sounds like a perfect deal for the folks across town.
Mets owner Steve Cohen’s cash and David Stearns’ moderating influence should cook up a really nice package for Bellinger, who should have a couple spots to play in Queens now that Brandon Nimmo’s been traded, Alonso left and Mark Vientos may be on the block. If nothing else, the collection of Bellinger and Jorge Polanco would give the club admirable depth both in a roster and lineup sense.
Destination: Mets
Tarik Skubal
OK, we just had to throw a changeup here, pun semi-intended.
Skubal’s pending free agency in Detroit has been the rustling in the basement that teams simply can’t ignore this winter. The rather obvious notion that Skubal will walk after this year into a free agency that should break all-time records for pitcher salary has turned all eyes on Detroit.
He’d certainly fit in L.A., a one-year rental to boost a pitching staff that will be licking its wounds from two World Series titles – and the Dodgers have perhaps the most prospects to offer. He’d certainly fit anywhere in New York, particularly since the Yankees believe their 94-win core was pretty good – and Skubal would lessen the sting of waiting for Gerrit Cole and Carlos Rodón to return from injury.
Yet there’s also an 87-win team that twice reached the ALDS, only to lose in heartbreaking fashion each time. A club with an interesting young core, a rebuilt bullpen, a ballpark perfect for Skubal to flourish one more time before hitting the market.
Rumblings are nice. But common sense prevails more often than not.
Destination: Tigers