Our MLB writers dream up some deals they think could happen this winter.
The hot stove is heating up — with 21 of our Top 50 free agents having landed new deals already this winter — but let’s not forget the other key component of offseason transactions: trades.
We’ve seen a few teams make deals already, including Sonny Gray to the Red Sox and the Mets’ and Rangers’ swap of Marcus Semien for Brandon Nimmo, but chances are the trade market is just heating up. So with that in mind, let’s lay out some deals we’d like to see happen this winter.
Mets acquire OF Luis Robert Jr. from White Sox for RHP Jack Wenninger and OF Nick Morabito
Perhaps Chicago’s decision to pick up Robert’s $20 million option for 2026 was made with the intention of dealing him at next year’s deadline, but with the dearth of enticing right-handed-hitting outfielders available in free agency, there’s no sense in waiting any longer to cash in on Robert as a trade chip. Although he finished the 2025 season on the injured list due to a hamstring strain, Robert was quietly hitting quite well before that (.297/.350/.469 over his final 35 games) and offers enough tantalizing upside to return real prospect capital. The Sox should find the best deal available this winter and finally pull the trigger.
Enter the Mets, in the midst of a total roster makeover, with the requisite farm system depth to meet Chicago’s asking price and the financial flexibility to take on Robert’s contract. The financial element shouldn’t be as important here; for the White Sox to secure the best prospect return, they are best off covering as much of Robert’s salary as possible (even if the Mets can afford it). But regardless of the money, New York is an ideal suitor as a team with a center-field need and a stated goal of improving defensively. While durability and recent volatility at the plate make Robert risky in some respects, he brings the same terrific defense as the incumbent Tyrone Taylor, but with dramatically more offensive upside. It’s also not necessarily a long-term commitment; Robert has another $20 million club option for 2027 that could be exercised if he flourishes or declined if he flops. In that case, the Mets could move forward with some of their internal center-field candidates who project to be ready as every-day options in 2027 (Carson Benge, Jett Williams).
As for the return, the Mets have enough depth at the upper levels to put together a worthwhile package without parting with any of their top names. Wenninger doesn’t carry the same cache as the three right-handers we saw debut for New York last season (Nolan McLean, Jonah Tong, Brandon Sproat), but he was terrific in a full season in Double-A, experiencing a notable velocity uptick and displaying a fantastic splitter as his go-to out pitch. He could break into a big-league rotation at some point in 2026, though it’s hard to see that happening in Queens. Morabito, whom the Mets added to their 40-man roster last month after a stellar showing in the Arizona Fall League, is a sensible inclusion in a Robert trade as a candidate to be Chicago’s center fielder of the future; there’s a severe lack of depth at the position behind Robert. Morabito will likely need some time in Triple-A first, but he’s a plus-plus runner who can be an impact defender and baserunner, and he has a decent offensive approach enabling solid on-base numbers despite minimal power. — Shusterman
Orioles acquire RHP Edward Cabrera and RHP Anthony Bender from Marlins for 1B Coby Mayo, RHP Michael Forret, LHP Joseph Dzierwa, RHP Levi Wells and INF Aron Estrada
At the 2024 trade deadline, Miami and Baltimore linked up on a trade borne out of each club’s positional surpluses, as the Marlins dealt from their depth of arms, sending lefty Trevor Rogers to the Orioles, in exchange for two hitters, Kyle Stowers and Connor Norby, who were unlikely to find regular at-bats in Baltimore anytime soon. It was a deal that seemed to lean heavily in Miami’s favor in the months afterward, but it now looks like a big win for both sides, with Rogers being downright dominant when on the hill for Baltimore in 2025 and Stowers blossoming into an All-Star for the Fish.
Eighteen months later, these two clubs could line up for a similar trade, with Baltimore still in search of pitching upgrades and the Marlins reportedly willing to deal from their rotation to bolster their young talent base as they look to launch out of rebuild mode. Whether or not Baltimore is able to add an impact starter in free agency, Cabrera is an ideal target as a high-upside right-hander who is under contract through 2028. Durability and command have been challenges at times, but Cabrera is comfortably above-average at coaxing both whiffs and groundballs, an enviable combination for a starting pitcher. And with Baltimore still in need of bullpen help — and the reliever free-agent market thinning out quickly — Bender, a solid seventh-inning option who is under contract for two more seasons, would be a nice bonus to this deal, even if he heightens the prospect cost.
The Marlins would rightly want a lot in return for these two pitchers, and the Orioles are one of the few teams in position to meet such a lofty ask. The addition of Alonso has rendered some of Baltimore’s upper-level hitters expendable, with Mayo the obvious candidate to be flipped in a trade. (Heston Kjerstad is another name to monitor, having seemingly been passed on the depth chart by Dylan Beavers, but Kjerstad’s 2025 was so poor that it’s difficult to gauge his trade value at present.) Mayo just turned 24 and finished strong with a .941 OPS in September; he could bring some much-needed thump to Miami’s lineup at a position of weakness at first base.
Among minor-league arms with at least 70 innings pitched in 2025, only Jonah Tong posted a lower ERA than Forret’s mark of 1.58 in 74 innings of work. The right-hander turns just 22 in April and has made only three starts in Double-A, but if he can prove he can handle a starter’s workload over a full season, he could be a top-100-type talent. Dzierwa was Baltimore’s second-round pick earlier this year and has plus command of a deep arsenal headlined by an excellent changeup. Wells throws very hard and has reached Triple-A developing as a starter, but a transition to a bullpen role could have him big-league-ready in short order. Estrada is a compact switch-hitter who has stolen 30-plus bases each of the past two seasons while playing mostly second base and left field. — Shusterman
Phillies acquire LHP Tarik Skubal from Tigers for RHP Andrew Painter, INF Aidan Miller, INF Aroon Escobar and LHP Mavis Graves
When the powers that be here at Yahoo asked me to concoct a trade for one Mr. Tarik Skubal, the first thing that popped into my mind was desperation. Not in regard to my editor — trade theorizing within reason is harmless and fun! Don’t be a hater! — but in regard to which team might have the guts to swing a deal for the best pitcher on Earth.
Stay with me here.
Skubal is a free agent after the 2026 season. His agent, Scott Boras, rarely shepherds his clients to extensions. A team that acquires Skubal this winter would probably have him for just one season. Given how much teams value their top prospects — and Skubal would require quite a haul — those are big stakes.
So who’s under that kind of pressure? Who is living in the here and now? Which team has to win in 2026?
The Padres come to mind. As do the Yankees and Red Sox. But I think the Philadelphia Phillies are the team most incentivized to do something completely irresponsible, to mortgage the future for one shot at glory. Remember, the clock is most certainly ticking at Citizens Bank Park, no matter how much blood Bryce Harper cycles out of his body. The Harper/Schwarber/Turner/Wheeler/Nola core is all 32 or older. Cy Young vote recipient Jesús Luzardo hits free agency next winter. So do infielders Alec Bohm and Edmundo Sosa.
A rotation led by Skubal, Luzardo and Cristopher Sanchez would curbstomp people. Whenever Zack Wheeler returns from his thoracic outlet issues, he can join the party, too. President of baseball operations Dave Dombrowski has a reputation of pushing the chips in, and who better to go all-in on than Skubal?
In this scenario, in return the Tigers get two close-to-the-bigs top prospects in Painter and Miller, a fun bat-first infielder in Escobar and a tall lefty in Graves from whom they can maybe coax more velocity.
The Phillies probably wouldn’t do something this aggressive. The Tigers probably won’t trade Skubal anyway. But this is the type of win-now, swing-for-the-fences move that contenders should be making more often. — Mintz
Marlins acquire OF Jarren Duran and DH Masataka Yoshida from Red Sox for RHP Edward Cabrera
What follows is a list of truths about the Boston Red Sox.
The Red Sox have too many outfielders. In order to ensure an optimal alignment — glovesmith Ceddanne Rafaela in center and not second base — the Red Sox need to trade either Wilyer Abreu or Jarren Duran because, well, hot-shot slugger Roman Anthony isn’t going anywhere.
The Red Sox would love to offload as much of DH Masataka Yoshida’s contract ($18.6 million in 2026 and 2027) as possible. Unfortunately, he has turned into an offensive zero and a roster clogger. His contract is relevant because the Sox seem skittish about journeying deep into the first tier of the competitive balance tax, even though they should be operating like a financial bully. To bring back Alex Bregman, Boston is going to have to make a big commitment. Jettisoning Yoshida might make that math more comfortable.
The Red Sox could use one more dependable starter. Chief baseball officer Craig Breslow already acquired Sonny Gray and Johan Oviedo to slot in behind über-ace Garrett Crochet this winter, but one can never have too much rotation depth. Adding Cabrera would then allow Breslow to use any number of the preexisting, non-Payton Tolle depth options (Connelly Early, Patrick Sandoval, Kutter Crawford, David Sandlin, Kyle Harrison) to acquire a hitter to replace Yoshida.
Why would the Marlins do this? Well, they probably won’t. This type of move doesn’t fit president of baseball operations Peter Bendix’s MO. If he parts with Cabrera, Bendix would probably want a player with more control than the three years left on Duran’s contract. But there’s certainly room on Miami’s payroll to absorb a bad contract such as Yoshida’s. The Marlins have run embarrassingly low payrolls the past few years and should start taking advantage of that space to acquire good players. If they don’t want to keep Yoshida, they can just cut him, but use the coin for something useful, for Pete’s sake.
That’s what Duran is. Sure, moving forward he’s probably not going to play like the MVP candidate he was in 2024, but the muscled-up outfielder is a productive player on the good side of 30 years old. The Fish have a chance to fight for a wild-card spot in 2026, and pairing Duran with Kyle Stowers and Jakob Marsee would give them one of baseball’s most underrated outfields. — Mintz
Red Sox acquire 2B Ketel Marte from Diamondbacks for LHP Payton Tolle, INF Kristian Campbell and SS Franklin Arias
The Red Sox have had their hand in a little bit of everything this offseason, and after striking out on big boppers Kyle Schwarber and Pete Alonso, they can get their guy with Marte. Marte isn’t your average second baseman. He’s one of the best players in baseball and just a year removed from a third-place NL MVP finish in 2024. The acquisition of Marte would give the Red Sox the elite bat they need in the middle of their lineup, without requiring the team to move many foundational pieces.
As for the Diamondbacks, they’re not going to trade an MVP-caliber player with six more seasons of club control for nothing. To make this trade, the Red Sox will have to give up a haul, moving top prospects Payton Tolle and Franklin Arías and former top prospect Kristian Campbell, who still has major upside. While Arias is about a year away from the big leagues, Tolle could slot right into Arizona’s rotation, and Campbell can take Marte’s vacant spot at second base and stay there after moving around in Boston.
This trade would help the Red Sox significantly, while Arizona would acquire multiple players who help their major-league roster both now and in the future. All that while still allowing the Diamondbacks the flexibility to make other moves to supplement their offense this offseason. — Dorsey
Mets acquire RHP Nick Pivetta from Padres for RHP Jonah Tong and INF/OF Jett Williams
It seems preposterous that after acquiring Nick Pivetta just a year ago, the Padres would be looking to move him. But with an ownership group in flux and a hefty payroll that has to come down, while trading the right-hander probably isn’t San Diego’s first choice, it might be what they have to do.
What makes a Pivetta trade more challenging than other potential deals is that the right-hander has an opt-out at the end of the 2026 season. There’s no guarantee that he opts into the two years, $32 million on his contract for 2027 and 2028, which means acquiring him is something of a gamble. That makes the perfect trade partner — one with a big need for starting pitching and one that can afford the risk if Pivetta opts out — the Mets.
In the return, Tong has generated interest all around baseball, and after a solid first showing in the big leagues, he’s the type of young arm the Padres have been looking for. Meanwhile, Williams has always been a talented player with lots of tools, but he’s somewhat blocked in New York’s system. A move to San Diego would allow him the chance to play in the big leagues.
This is a solid trade that makes sense for both sides, and if Pivetta pitches well in Queens, he can assure himself another strong payday next offseason. — Dorsey
Category: General Sports
