There’s no nifty little trinket awarded to the team that “wins” the winter meetings. And no, satisfying the media-industrial complex by being the most active team doesn’t count.
Still, as 30 Major League Baseball clubs converge on the synthetic exterior of Orlando for baseball’s annual transactions bazaar, some franchises could stand to make a little noise. Of course, the three-day affair is no hard deadline to add or subtract personnel, and many bold-faced names will loiter on the market, perhaps into the new year.
But proximity can certainly breed activity. With that, we examine five teams who could – or should – shake things up this week:
Boston Red Sox
Their quick strike to reel in Sonny Gray shows evidence of a winter plan they’d like to execute with dispatch. And there’s little ambiguity regarding two of the top free agent targets to which they’ve been consistently linked: Alex Bregman and Pete Alonso.
Both are Scott Boras clients who suffered through a long December a year ago as draft-pick compensation was attached to their free agency. This time around, they are truly free agents, with Bregman bringing the perk of familiarity with the Red Sox.
Bregman’s one season in Boston – he opted out of the final two seasons of a $120 million deal to do this again – was a smash, save for injuries that limited him and his .821 OPS to 114 games. Still, Boston climbed out of .500-ville and made the playoffs for the first time since 2021.
We know Boras clients can linger on the market. Yet there are few secrets with these guys and, after one trip around the sun last winter, agent and players know what’s out there. With Boston’s desperate need to fortify its lineup – and still armed with most of the $250 million cost savings from the Rafael Devers deal – a quick strike for one (both?) of these guys is logical.
Baltimore Orioles
Their money was no good last winter, when Corbin Burnes declined their aggressive offer to stay near his Arizona home and now, the Orioles have no choice but to reel in pitching help.
It stood to reason they might get outbid for Dylan Cease, whose elite strikeout rate earned him a $210 million deal with the rival Toronto Blue Jays. But drop down a tier, and the fit could be just about right.
Left-hander Framber Valdez would be a strong and not thoroughly cost-prohibitive match in Baltimore. Durable, playoff-tested and originally signed by the Houston Astros when current Orioles baseball chief Mike Elias was scouting director, Valdez would provide a crucial anchor for an Orioles staff with several question marks.
The early smoke has indicated Elias has been in on all the key free agent targets – Cease, Valdez, Zac Gallen and Ranger Suarez. In a winter in which the Orioles simply cannot come up empty in their pitcher search, jumping quickly into the market could be particularly important here.
Arizona Diamondbacks
They hold one of the more valuable trade chips this winter: An All-Star hitter on a team-friendly deal who can bolster anyone’s infield. And if and when they deal Ketel Marte, the Diamondbacks will still have an economically friendly core to build around in shortstop Geraldo Perdomo – who finished fourth in NL MVP voting – and right fielder Corbin Carroll.
So, they have options. And they can look around an NL West in which the Dodgers will find it doubly hard to three-peat (that tax bill for October pitcher usage will come due), the Padres are receding financially and the Giants might suddenly grow wary of all the nine-figure deals they’re suddenly carrying and believe they can sneak through the field.
It’s unfortunate they’ll be without Burnes in 2026 due to Tommy John surgery in June, but jumping into the pitching market will both help backfill the likely loss of Gallen but also equip them for a future that includes Burnes. A team with holes to fill and options to create further flexibility.
Toronto Blue Jays
The winter parlour game of free agency got a lot more interesting once these guys jumped in annually. Perhaps their Cease signing will be the loudest noise they make, but it’s not likely.
And it won’t be for lack of effort. The Blue Jays may face an either-or situation with regard to top free agent prize Kyle Tucker and their own superstar, infielder Bo Bichette. Unless they truly want to become New York North, Strong and Free, signing both seems unlikely – it would put total commitments to just three players (including $500 million man Vladimir Guerrero) over $1 billion.
Yet they cannot afford to miss on both if they want to maintain these best of times – and the Cease signing indicates they will try like hell to improve on their runner-up finish in the finals. Always keep an eye on these dudes.
Detroit Tigers
Oh, we’re not expecting Tarik Skubal to move. The public appetite for Big Transaction often tramples over the fact that some teams actually want to win.
Combine that with the fact that there’s no universe in which the Tigers get “market value” for a two-time AL Cy Young Award winner and yep, there’s likely no offer that could move them to move Skubal.
Instead, think of this as their all-in year.
Ownership and baseball ops chief Scott Harris fully realize retaining Skubal is probably impossible. Thus, the Tigers’ “win curve” may never bend more north than it will in 2026. That’s probably why they’ve been connected once again to Bregman, who turned down $171 million from them last season.
If nothing else, the Bregman engagement indicates they’re not willing to trudge to an AL Central title or a third wild card while leaning too hard on the Zach McKinstrys and Wenceel Perezes of the world, whose best usage might be in a lesser role.
No, it makes sense for the Tigers to go for it now. And maybe make a little noise this week.