MLB Offseason Heats Up: Executives Weigh In on Biggest Storylines
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.”
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.
Who Will Sign Japanese Ace Tatsuya Imai?
Survey says: Giants 5, Yankees 3, Dodgers 3, Cubs 2, Blue Jays 1, San Diego Padres 1
We’ve got you covered on all the major hot stove signings and trades.
Tracker » | Free agency, trade grades »
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.
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.
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
How much will the biggest stars get paid this winter? Kiley McDaniel breaks down the 2025-26 free agent class. Rankings, contract projections »
There’s no real consensus here, but one commonality between the players listed above: Nearly all of them are over 30 years old.
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.
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.
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
How should fantasy managers react to all of the wheeling and dealing going on this offseason? Our experts offer up their takes.
Fantasy reaction to free-agent signings, trades »
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.
