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Jesse Rogers
The hot stove started simmering early this MLB offseason — and shows no signs of slowing down.
The Seattle Mariners kicked the winter off by re-signing Josh Naylor, followed by the Los Angeles Angels and Baltimore Orioles pulling off an early trade. Then the Texas Rangers and New York Mets upped the ante with a Marcus Semien-for-Brandon Nimmo swap before the Boston Red Sox acquired Sonny Gray from the St. Louis Cardinals on Tuesday.
Before things heat up again after Thanksgiving, we polled 16 MLB executives on what’s to come the rest of the winter, from which teams will be busiest to where the biggest free agents will land. (Respondents were given the choice to skip any questions, so not every answer has 16 votes.)
Will Kyle Tucker get more than $400 million, and who will give it to him?
Survey says: $400 million? Yes 6, No 10
Who will sign him? New York Yankees 6, Los Angeles Dodgers 4, Toronto Blue Jays 3, Detroit Tigers 1, Philadelphia Phillies 1, Orioles 1
The good news for Tucker is that nearly every executive who voted “No” on him making more than $400 million said it would still be close. If not for a couple of second-half injuries this season, it probably wouldn’t even have been a debate (his 143 OPS+ in 2025 still matched his total from 2023, when he finished fifth in MVP voting). In fact, one executive opined that if Tucker was healthy the entire season, the above dollar figure would start with a five, not a four.
“I see it at $350 million over 10 years,” one exec said. “My prediction is the Yankees.”
“I don’t think he gets to $400 million,” another said. “Seems to me the right number will be in the mid-300’s … but as we always say, it only takes one, so I wouldn’t be completely shocked if it ended up starting with a four. I think he ends up with the Yankees.”
“My prediction is that he will sign an [Alex] Bregman-type deal with a shorter-term, higher AAV and opt-out(s) in hopes of having a monster season in ’26 or ’27 and hitting the [free agent] market again coming off a better year,” another voter responded. “The Yankees seem well positioned for a deal like that.”
The Yankees kept coming up in answers, but they weren’t the only ones. One respondent thought Baltimore or Detroit could put more than $400 million in Tucker’s pocket and the voter who chose Philadelphia did it with the caveat of Kyle Schwarber leaving. But coming in second in our poll were the back-to-back World Series champions.
“I think he does get there on a longer deal with lower AAV with opt-outs,” an executive said. “Hate to say it, but probably Dodgers.”
Another added: “The Dodgers have need in the outfield. Some of their hitters are getting older. They have everything they need on the mound. Now they need to help their offense.”
Where will the top 3 free agent starters with MLB experience sign?
(Editor’s note: After this story was published, the Toronto Blue Jays and Dylan Cease agreed on a 7-year, $210 million deal.)
Survey says:
Framber Valdez: Blue Jays 5, New York Mets 4, Orioles 4, Tigers 1, Houston Astros 1
Dylan Cease: Mets 6, Blue Jays 3, Red Sox 2, Atlanta Braves 2, Chicago Cubs, 1, San Francisco Giants 1
Ranger Suarez: Red Sox 4, Phillies 4, Blue Jays 3, Braves 2, Giants 1
The Blue Jays showed up as possibilities for each pitcher, as executives believe they will add to their team after making the World Series and coming so close to winning it all this past season.
“I could see the Blue Jays adding a lefty like Valdez,” one executive said. “He fills a need and might send them back to October baseball.”
The Mets weren’t far behind in the voting, considering their starting staff was a mess late in the year and they relied on rookies down the stretch. The only pitcher several voters believe even has a chance at returning to his old team is Suarez.
“With [Zack] Wheeler out, I think Suarez goes back to Philadelphia,” another exec said. “It’s kind of like Schwarber. They need him more than he needs them.”
A voter who chose Atlanta for Cease called it “low-hanging fruit” since he’s from the area, adding: “The Battery/new ballpark has been a financial boost for them.”
Who will sign Japanese ace Tatsuya Imai?
Survey says: Giants 5, Yankees 3, Dodgers 3, Cubs 2, Blue Jays 1, San Diego Padres 1
The usual suspects, plus Toronto, show up here — most of these teams have been perennial favorites for Japanese players coming over to MLB for the first time. These teams are among those with a leg up on the rest of the competition as they’ve put time, money and energy into recruiting in Japan. At 27 years old, Imai is the right age for a multiyear deal and should benefit from the success of others from Japan that came before him.
“The Giants have been in the hunt [for a Japanese pitcher] in the past; pairing Imai with Logan Webb makes a ton of sense,” one executive said.
Unsurprisingly, the Dodgers were tied for the second-most votes, as they have secured the top three Japanese free agents over the past two offseasons in Shohei Ohtani, Yoshinobu Yamamoto and Roki Sasaki.
“Dodgers,” another said. “Seems like they have that market somewhat cornered.”
Chicago, who extended a qualifying offer to Japanese left-hander Shota Imanaga this winter that was accepted, is also in the mix.
“The Cubs have already stated they need more pitching, and they should have room even after Imanaga returned,” another executive stated.
Which of these hitters — Schwarber, Bregman, Cody Bellinger and Pete Alonso — will return to their original team?
Survey says: Schwarber 7, Alonso 4, Bregman 4
What’s most interesting is not who got votes for this question — Schwarber makes sense as the leading answer here — but that not a single person has Bellinger returning to the Yankees. He provided some much-needed balance to their lineup, so if he walks, perhaps it does open the door for Tucker in New York — as respondents indicated in their answers to the earlier question.
As for Schwarber, Alonso and Bregman, voters had similar lines of thinking: These are players who are crucial to their respective teams, which paves the way for a potential reunion.
“The Phillies need Schwarber more than he needs them, so in pure contract terms, they may have to overpay,” one executive said. “But he’s worth it. He’ll stay.”
“At this point, Alonso is synonymous as a Met,” another voter said. “He’s the most popular player. And he can hit. They need him.”
“Bregman provided so much [leadership] for Boston and that park is perfect for him,” another executive said.
Which free agent contract is going to raise the most eyebrows?
Survey says: Edwin Diaz 2, Bo Bichette 2, Schwarber 2, J.T. Realmuto 2, Zack Littell 1, Lucas Giolito 1, Munetaka Murakami 1
There’s no real consensus here, but one commonality between the players listed above: Nearly all of them are over 30 years old.
Age is something that always gives teams some pause — and the only reason Schwarber shows up here: “The contract length for an aging designated hitter will be the most surprising part,” one voter said.
An executive who chose Diaz in this category simply noted the length of the potential deal and the volatility of the position.
“Diaz is set to cash in, but how many times do we see that backfire for closers?” another voter brought up. “Not always, but often.”
Bichette and Murakami are the only two players given as answers to this question who aren’t yet 30 years old — but that doesn’t mean they don’t have concerns of their own.
“I’m just thinking about the years for Bichette and where he’ll play and all that,” one executive said. “His contract will be most interesting to me.”
“My pick is Murakami,” another said. “Seems like the league is mixed on him due to swing-and-miss concerns.”
What will the Tigers do with Tarik Skubal this offseason — trade him, extend him or let it play out?
Survey says: Let it play out 10, trade him 3, sign/extend him 0
Letting it play out might have been the easy answer here — though, it could also easily be the right one. It kicks the Skubal decision down the road and opens a just-in-case door: If the Tigers’ 2026 season isn’t going well, then dealing him at the July trade deadline will make it a lot easier to swallow.
“I doubt they can afford to extend him, but they also know they can’t win the division without him. I think they roll with him in ’26 unless they get blown away with a trade concept,” one executive said.
Of course, letting the situation play out comes with its own set of risks.
“The longer they wait to trade him, the stickier it gets,” another voter stated. “Value could go down or perhaps worse, if you’re ownership. He gets off to another Cy Young start and fans start screaming even louder to sign him.”
Of course, signing him now would undoubtedly be nice for Detroit fans, but not one respondent thought that would happen this winter.
Who is the top trade candidate of the winter not named Skubal?
Survey says: Joe Ryan 2, Freddy Peralta 2, Ketel Marte 2, MacKenzie Gore 1, Steven Kwan 1, Luis Robert Jr. 1, a Pirates starter 1
There is no shortage of trade candidates this offseason, as there are several teams seemingly willing to move pitching. That’s not the case every winter, but for whatever reason — team friendly salaries, players nearing free agency, payroll shedding — we might see more movement on the mound than usual ahead of the 2026 season. (Two respondents from our poll chose Gray for this question, and they proved to be right after Tuesday’s deal sent the hurler to Boston.)
“The Twins were in the trade market over the summer, testing the waters on Ryan,” one executive said. “I think that leads to him getting moved this winter.”
“I don’t know if Peralta’s salary [$8 million] makes him more or less desirable for the [Milwaukee] Brewers to move him, but they’ll probably do the opposite of what everyone is thinking!” one exec half-joked. “And it’ll work.”
One respondent coyly mentioned a Pirates starter getting moved — but didn’t specify which one. Several mentioned keeping an eye on the Rangers as they look to cut payroll, though the trade of Semien for Nimmo didn’t necessarily accomplish that in the short term. The Rangers don’t seem to be done with their wheeling and dealing.
There were also a couple of surprising answers.
“Sleeper name: Tyler Glasnow,” said one voter. “Feels like the Dodgers can go to Ohtani, Yamamoto, [Blake] Snell, Sasaki, [Emmet] Sheehan and others and use Glasnow on the trade market to cover up holes.”
And what’s an MLB offseason without a blockbuster trade prediction.
“Blockbuster alert: Ketel Marte,” one voter simply stated.
Which smaller-market team will make the most noise this winter?
Survey says: Pittsburgh Pirates 5, Cincinnati Reds 3, Kansas City Royals 3, Miami Marlins 3, Tampa Bay Rays 2
Stop if you’ve heard this before, Pirates fans: Ownership is going to spend. Actually, you probably have not heard that before this winter, but that sentiment has picked up steam early this offseason. Even agents are feeling cautiously optimistic about it.
“The Pirates better pair a good hitter or two with [Paul] Skenes or else we all know what happens,” one executive said. “There’s been enough chatter. I vote for them.”
Either way, there has been more chatter in general about small-market teams spending this winter. Are the Reds one big bat away? Will the Marlins’ surprising season lead them to some aggressive signings? And everyone knows the Royals need hitting.
“Both Pittsburgh and Kansas City have top-of-the-game superstars that they need to support with more money,” one voter said. “The noise from Pittsburgh has already started but I will go with Kansas City because I think they spend the most on one player.”
“Remember, the Rays have new ownership,” another executive said. “It may not show up in payroll this offseason, but it should soon.”
One voter who chose the Reds didn’t mince words: “Their lineup was not very good; they likely know they need to upgrade their position player group. Schwarber went to high school in the Cincinnati suburbs.“
Maybe it’s the year of the small market!