MLB's Biggest Winners and Losers of Free-Agent and Trade Season So Far
Winning Major League Baseball's offseason doesn't guarantee anything during the regular season, but it can be a big step in the right direction.
So, which teams have made the biggest strides (in either direction) thus far this winter?
On the one hand, it's still early. In fact, the winter equinox isn't until Sunday, and then we have three more months until Opening Day. Moreover, most of the cream of the crop free agents—Kyle Tucker, Bo Bichette, Framber Valdez, Alex Bregman, etc.—are still available, so there's ample opportunity remaining for early losers to become winners.
On the other hand, deals have been struck with 21 of the 42 players (50 percent) who appeared atop MLB Trade Rumors' ranking of the best free agents in early November, so we have kind of reached the halfway point of the offseason.
No time like the present for an update on who's crushing it and who's crashing out.
Winners and losers are presented in no particular order, aside from oscillating back and forth.
Winner: Baltimore Orioles
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Though we are still waiting to see if the Orioles are going to accomplish what we assumed was their main goal of the offseason—land a top-of-the-rotation type of starting pitcher—they sure have been busy with the rest of the roster.
In what was one of the first moves of MLB's offseason, they reacquired Andrew Kittredge from the Cubs. And toward the end of November, they made Ryan Helsley their first noteworthy signing of a free agent.
There were major questions about this bullpen heading into the offseason, with Félix Bautista likely to miss most, if not all of the 2026 campaign. But in getting Helsley and Kittredge to join forces with Keegan Akin and Yennier Cano, things suddenly aren't looking too shabby.
In between those additions to the bullpen, the O's traded Grayson Rodriguez for Taylor Ward, adding a big bopper to the outfield/DH mix for his final year of arbitration eligibility.
But, of course, what really made Baltimore a winner was landing Pete Alonso.
Time will tell if this nine-figure contract works out better than the one it gave Chris Davis a decade ago, but this team is far more intriguing than it was seven weeks ago, with what could be the best offense in the American League.
If the Orioles end up also adding Framber Valdez or Ranger Suárez to the rotation, that bandwagon is going to fill up in a hurry.
Loser: Milwaukee Brewers
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It has become an annual rite of passage at this point: We bemoan the Brewers' uninspiring winter, but then they enter October as one of the viable candidates to win it all anyway.
This time around, though, the bummer isn't that they lost a key player like Corbin Burnes or Willy Adames, but rather that their qualifying-offer gambit on Brandon Woodruff turned into an expensive one.
Had Woodruff declined the offer, Milwaukee would've gotten a solid compensatory draft pick once he signed elsewhere. Instead, he's back for one more year at $22.025M, becoming the highest-salaried pitcher in franchise history.
Sure, they'll be happy to have him back on the mound for however many innings he's healthy enough to pitch in 2026. But after having to pay him $10M when he declined his $20M mutual option, that additional $22.025M is tough to swallow/budget.
Though the buyout doesn't count against their payroll for luxury-tax purposes, it's not like the Brewers are ever worried about paying a tax. Altogether, that is $32.025M in one year for a team that has opened each of the past two seasons with a payroll of around $105M, devoted to a pitcher who has made a combined 23 starts over the past three years.
At least they've got Freddy Peralta for $8M, provided they don't trade him away?
The Brew Crew subsequently traded breakout outfielder Isaac Collins and right-handed reliever Nick Mears to Kansas City for left-handed reliever Ángel Zerpa, which was a bit of a head-scratcher. We'll see if they can afford to do any more spending.
Winner: Relief Pitchers
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As of Thursday morning, of the 67 players listed in the "Signed Free Agents" tab on Spotrac, 36 (or 53.7 percent) are relief pitchers.
And while there are plenty down in the "barely $1M" range, there are already 10 bullpen arms who have signed for at least $16M.
Edwin Díaz became the highest-salaried reliever of all time with his three-year, $69M contract in Los Angeles.
Devin Williams struggling in his one season with the Yankees didn't prevent the Mets from giving him $51M over three years.
Ryan Helsley still got $28M for two years with Baltimore despite his disastrous second half of 2025.
Atlanta signed two closers, bringing back Raisel Iglesias for $16M while also landing Robert Suarez on a $15M AAV for three seasons. Detroit also nabbed a pair of closers in Kenley Jansen for $11M and Kyle Finnegan for two years, $19M.
Throw in Tyler Rogers getting $37M from the Blue Jays to presumably serve in a set-up role for the next three years and it was a lucrative early offseason for relievers.
Conversely, best of luck to the teams that missed the boat here while focusing on other endeavors. Both Pete Fairbanks and Seranthony Domínguez are still out there as solid options, but arguably the 11 best free-agent relievers are already off the board.
Loser: San Diego Padres
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With the Padres in particular, history shows that wheeling‑and‑dealing season is never truly over until it's over.
Because while AJ Preller has made more than his fair share of blockbuster moves over the years, he has never been shy about waiting out the market.
Last winter, the Padres did little of note until the end of January and still ended up getting Nick Pivetta and three guys who were regulars in their starting lineup early in the season in Gavin Sheets, Jason Heyward and Elias Díaz.
Then, they completed nothing until deadline day when they added all of Mason Miller, JP Sears, Ryan O'Hearn, Ramón Laureano, Freddy Fermin, Will Wagner and Nestor Cortes in the span of about six hours.
So, no, we're not concerned that prior to re-signing Michael King on Thursday, the only move they had made this winter was signing a 28-year-old reliever with 23 innings of MLB experience (Ty Adcock).
However, if we're choosing winners and losers from what we've seen thus far, this is clearly one of the bigger losers, having done virtually nothing to replace Dylan Cease, Robert Suarez, Luis Arráez and Ryan O'Hearn.
We also found out on basically day one of MLB's offseason that Yu Darvish underwent UCL surgery and won't pitch in 2026. (Or possibly ever again?) So, they've lost even more than expected, need to work with a limited budget and have an ownership family that is "exploring strategic options" for possibly selling the team.
(And all the while, the rival Los Angeles Dodgers just keep getting stronger.)
Winner: Toronto Blue Jays
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The first big step of the offseason is players and clubs making decisions on contract options. The vast majority of those decisions are entirely unsurprising, but Toronto was almost certainly the biggest winner of that stage of the offseason with Shane Bieber choosing to remain a Blue Jay for one more year at $16M.
Toronto was also the first team to ink a marquee free agent, signing Dylan Cease to a seven-year, $210M deal.
It was a fair amount more than most were expecting Cease to fetch, but he is a strikeout machine who never misses a turn through the rotation and has always had strong underlying metrics. He should be the intimidating anchor that this rotation was missing in 2025, and if they overpaid a bit for that, so be it.
The Blue Jays subsequently added Cody Ponce to their rotation depth after his dynamite 2025 campaign in Korea. If that even remotely translates back to North America, he could be a steal on a $10M salary for the next three years.
The cherry on the sundae was signing one of the best and most durable setup guys in the business in Tyler Rogers.
With a payroll that is already pushing $300M, can they still afford to bring back Bo Bichette? Or sign Kyle Tucker? Heading into the offseason, it felt likely Toronto would do one or the other.
Perhaps the better question is: With the additions the Blue Jays have made, do they really need to add anything else at this point in order to repeat as AL champions?
Loser: Positions Impacted by Posting Windows
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Three of the 20 or so biggest free agents available this winter played in Japan in 2025: 3B Munetaka Murakami, RHP Tatsuya Imai and 3B Kazuma Okamoto.
None of the three has signed with an MLB team yet, but the clock is very much ticking, each needing to sign before his 45-day posting window closes, lest they continue their Nippon Professional Baseball careers.
For Murakami, that window closes at 5 p.m. ET on Monday, as he was posted on Nov. 7. The other two have a little longer because they weren't posted until later in November. Imai's negotiating window can stay open until Jan. 2, while Okamoto has until Jan. 4.
Because of the known deadlines on those three players, the market involving the traditional, MLB free agents at those positions has been unusually slow to develop—with the exception of Toronto making Dylan Cease an offer he couldn't refuse.
Not a single third baseman has signed yet this winter, as Alex Bregman and Eugenio Suárez highlight the stockpile of hot corner options who have essentially been forced to wait on the Murakami sweepstakes to run its course.
Similarly, there has been no indication yet that any of Framber Valdez, Ranger Suárez or Zac Gallen is on the verge of choosing a new mound to call their own.
We did get the Michael King news on Thursday, as well as Merrill Kelly re-signing with the Diamondbacks earlier in the week. Aside from those two and the Cease deal, though, the few starting pitchers who have signed are mostly reclamation projects such as Dustin May and Alek Manoah, or gambles like Cody Ponce, Drew Anderson and Steven Matz.
Both the third base and starting pitcher market should heat up very soon, though. Got to at least assume the Bregman wheels will start churning by Monday night.
Winner: Atlanta Braves
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In stark contrast to last offseason—when Atlanta's only noteworthy moves prior to signing Jurickson Profar in late January were declining its club option on Travis d'Arnaud and trading Jorge Soler for Griffin Canning before non-tendering both Canning and Ramón Laureano—the Braves have been quite aggressively in "asset acquisition" mode this winter.
We mentioned the re-signing of Raisel Iglesias and the signing of Robert Suarez. What a one-two late-inning punch that should be for a bullpen that also has southpaws Dylan Lee and Aaron Bummer still in the mix, plus Joe Jiménez returning after missing all of 2025 to a knee surgery.
But Atlanta also made three major additions to its position-player arsenal, bringing back Ha-Seong Kim for $20M after he declined his $16M player option, trading Nick Allen's career .535 OPS for the wildly versatile Mauricio Dubón and signing Mike Yastrzemski to a two-year deal to serve as the fourth outfielder.
Barring injury, all five are locks for the 26-man Opening Day roster, which already appears to have far more quality depth (read: injury insurance) than it did in recent years.
The Braves said at the beginning of the offseason that they intended to put together a top-five payroll, and they are pretty much there. Might have to settle for No. 6 with the way the Dodgers, Phillies, Blue Jays and both New York teams are positioned to blow well past the luxury-tax threshold, but they've put in some serious work in hopes of bouncing back from this past season's huge letdown.
Loser: Pittsburgh Pirates' Grand Spending Plans
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Did you allow yourself to believe the Pittsburgh Pirates were actually going to be big spenders this offseason?
If so, are you enjoying the view from flat on your back, Charlie Brown? Because Lucy went and pulled that football yet again.
The Pirates said they wanted Josh Naylor, but reportedly never actually made him an offer before he re-signed with the Mariners.
They did make an offer to Kyle Schwarber, but it was only a four-year proposal while everything seemed to be pointing toward (and ultimately resulted in) him getting five years on his nine-figure deal.
It was a big offer; would have been the biggest contract in franchise history. But was it sincere? Or did they fully expect to get outbid and just wanted to be able to say they tried?
Meanwhile, the only moves they've actually made were signing Gregory Soto to a one-year, $7.75M deal and trading Johan Oviedo and two prospects to Boston for two prospects.
(Let the record show Oviedo was my pick in November for the Pirate most likely to be traded this offseason, because, of course, this notoriously frugal franchise would try to avoid spending an estimated $2M on an expendable, arbitration‑eligible pitcher.)
There's technically still plenty of time to change the narrative. However, after opening each of the past two seasons with an estimated 26-man payroll of $86.4M, their current projected 26-man payroll (with only eight players slated for more than the league minimum salary of $820k) is $65.9M.
Winner: Middle Infielders
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Technically, Jorge Polanco is no longer expected to spend any meaningful time as a middle infielder. He'll be manning first base and/or DH duties in a New York Mets infield where Francisco Lindor and Marcus Semien get all the shortstop and second base reps they can handle.
Just about his entire career had been spent at either short or second, though, and now Polanco will be making $40M over the course of the next two seasons—after making $45.9M across his first 12 years in the big leagues.
And he's not the only current/former middle infielder who has already made bank this winter.
Ha-Seong Kim made little impact in 2025 after missing the first half of the season while recovering from shoulder surgery, but he, too, will be bringing in a $20M salary in 2026. He bet on himself, declined his $16M player option and got a 25 percent raise to remain Atlanta's primary shortstop.
Both of those signings happened after Gleyber Torres accepted his $22.025M qualifying offer from the Detroit Tigers. The second baseman got $15M in free agency last winter, and getting a nearly 50 percent raise while skipping the stress of waiting for the phone to ring was simply too good to pass up.
None of the three is exactly a superstar, but each has a 2026 salary that currently ranks top 30 among infielders. And if that's the going rate for guys like Polanco and Kim, that bodes pretty well for Bo Bichette, right?
Loser: New York Mets
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Edwin Díaz was arguably the best closer in all of baseball in 2025, as well as in 2022 and 2018. But he opted out of the final two years on his contract, declined New York's qualifying offer and turned down their reported three-year, $66M contract to instead sign with the Dodgers for $3M more and "because they are a winning organization."
In Díaz's stead, the Mets have invested $73M in Devin Williams (three years, $51M) and Luke Weaver (two years, $22M), who did such a mutually problematic job in clutch situations for the other New York team this past season that the Yankees went out and traded for David Bednar, Camilo Doval and Jake Bird ahead of the deadline, hoping to find something that would work.
The Mets also made no real effort to prevent Pete Alonso from signing with the Orioles, pivoting instead to giving Jorge Polanco $40M over two years to become perhaps the primary first baseman—a position he has never played at any point in his MLB or minor league career.
While allowing those two fan favorites to walk, they actively got rid of a third one, trading Brandon Nimmo for Marcus Semien in the name of improving the defense. But as we wait to see if they're going to sign either Kyle Tucker or Cody Bellinger, the current outfield situation is Juan Soto, Jeff McNeil and Tyrone Taylor.
Worst of all, they've done nothing whatsoever thus far about their starting rotation, which posted a 5.27 ERA over the final 93 games and was perhaps indisputably the main reason they crashed, burned and missed the playoffs.
Whatever expectations you had for the 2026 Mets two months ago, it's hard to imagine those haven't gotten markedly worse.
