Answering 6 questions looming over Winter Meetings

December 2nd, 2023

With the Winter Meetings set to begin on Sunday, we asked insiders Mark Feinsand and Jon Paul Morosi to address some of the key Hot Stove questions on every fan’s mind right now.

1. Which team will be the most active at the Winter Meetings?

Feinsand: It feels like a safe bet to say the Yankees, who will presumably continue to talk with the Padres about a Juan Soto trade (more on that later) while pursuing free agents, including Yoshinobu Yamamoto. But my answer here is the Cubs, who didn’t bring in manager Craig Counsell to sit by and watch the Hot Stove season pass them by. Facing the loss of Marcus Stroman, Cody Bellinger and Jeimer Candelario, Chicago is looking for at least one starting pitcher, an outfielder and a third baseman this winter, so president of baseball operations Jed Hoyer should be a busy man in Nashville.

Morosi: The Giants. We know the story of their 2022-2023 offseason, in which they fell short of securing massive contracts for Aaron Judge (his choice) and Carlos Correa (their choice). After changing managers following a losing season, the Giants are keen to send a message that they won’t tolerate mediocrity. They haven’t reached the postseason since the retirement of Buster Posey. In a division that boasts the Dodgers and defending NL champion D-backs, the Giants must bring in a new wave of difference-making talent.

2. Which major free agent is the most likely to sign by the end of the Meetings?

Feinsand: Jordan Montgomery. Unlike Blake Snell, Montgomery isn’t necessarily waiting for Yamamoto to sign in order to set a market for his own deal. We’ve already seen Aaron Nola, Sonny Gray and Kenta Maeda sign new deals this offseason, so there’s no reason to think Montgomery won’t do the same. Plenty of teams with money to spend need starting pitching, so Montgomery should have a number of suitors. If he finds a deal he likes with the right team, I think he could come off the board this week.

Morosi: Yoshinobu Yamamoto. The interest in him has been robust. Teams are willing to build their offseason around the right-handed ace because of his appealing age and proven track record in NPB. Franchise-defining contracts often wrap up during the Winter Meetings, as we saw with Judge one year ago. This week is a natural pivot point in the offseason, during which clubs need to assess how realistic their top choices are. Yamamoto’s market should narrow accordingly in the coming days.

3. You answered five key Shohei Ohtani questions last week. Has your opinion on his timeline or likeliest landing spots changed at all since then?

Feinsand: I haven’t changed my opinion that the Dodgers are the favorites; I would still take them against the rest of the field in the Ohtani sweepstakes. It sounds like the Mets and Red Sox have turned their attention elsewhere, though the Blue Jays are certainly getting a lot of buzz as a potential sleeper team. We still have no idea whether Ohtani is open to a move east (or north, for that matter), so whether he would consider Toronto remains to be seen. I still think this comes down to the Dodgers and Giants, with the Angels holding out a faint hope that they can bring him back to Anaheim.

Morosi: No. The Dodgers are the favorites to sign Shohei Ohtani, and they will remain as such until proven otherwise. There’s been plenty of buzz surrounding the Blue Jays since we discussed them in last week’s edition, but I don’t believe they have eclipsed the Dodgers as the leading possibility.

4. Will Juan Soto be traded by the end of the Meetings? If not, will it happen at some point this offseason, and what is your best guess on the team?

Feinsand: I believe we will see a few notable trades during the Meetings, with Soto potentially being the biggest. If the Padres are going to trade him -- and all indications is that they are -- then getting it done soon will allow GM A.J. Preller to carry on with the rest of his winter business.

The Yankees remain the most logical landing spot for a few reasons: 1) They have the young, Major League-ready pitching the Padres covet. 2) They can absorb Soto’s $30 million-plus salary for 2024. 3) They can afford to re-sign Soto (or extend him, if that’s something Soto and Scott Boras are open to) and keep him in pinstripes for years to come. The Yankees need his lefty power bat as much as any team in baseball, and as long as the Padres aren’t asking for the moon and the stars, I think these two teams find a way to get a deal done.

Morosi: No. Juan Soto will be a Padre at the end of the week, but he will wear a different uniform on Opening Day. The Yankees are my choice to land Soto, because they have a solid base of prospects, an obvious need for his skill set and financial resources to provide hope of retaining him long-term. Yankees left-handed hitters combined for only 55 home runs last year, second fewest in the American League. That needs to change in 2024.

5. Mike Petriello recently broke down five big-time starting pitcher trade candidates. Will any of those starters move at the Meetings? Which of the five is the most likely?

Feinsand: Tyler Glasnow. The Rays don’t tend to mess around when they have an objective, and in this case, it’s shedding Glasnow’s $25 million salary. I have heard from other executives that he will “definitely” be traded, and if that’s the case, I would expect president of baseball operations Erik Neander to move quickly. This doesn’t strike me as a situation that will drag into 2024.

Morosi: Dylan Cease. I was told recently that the Cease trade talks have intensified, and a deal could happen while we’re in Nashville. The Braves -- Cease’s hometown team -- are among the finalists to land him. The Giants and Dodgers are possible suitors, as well, depending on the outcome of their free-agent pitching pursuits.

6. Give us one sleeper team that could strike for a big move at the Meetings.

Feinsand: I’ll go with the Marlins. Coming off an 84-win season in 2023, there is some momentum building in Miami, even with Sandy Alcantara set to miss next season following elbow surgery. New president of baseball operations Peter Bendix has had a few weeks to assess his system and his roster, and based on his experience with the Rays, I would expect him to get creative on the trade front. Miami needs an impact bat -- something there aren’t a ton off on the free-agent market -- but perhaps Bendix can identify one on another club and pull a deal during the Meetings.

Morosi: The Twins. They have multiple rotation vacancies after the departures of Sonny Gray and Kenta Maeda, so they have little choice but to be active. And given the relative shortage of impact bats available in free agency, they could find a strong trade market for outfielder Max Kepler.