Major League Baseball's Winter Meetings are upon us. Even as the march of technology makes such an in-person, face-to-face hootenanny seem quaint and even unnecessary, it's still the signature event of the sport's offseason calendar. Speaking of signatures, the expectation is that a number of premium free agents will put pen to paper during the festivities that get underway on Sunday in Nashville, or at least lay the foundation for doing so. And that's to say nothing of the blockbuster trades that might go down. 

Such an event demands that we gin up enthusiasm and speculation, and we're here to satisfy those solemn duties by posing the most pressing questions that may or may not be fully or even partially answered before execs, agents, and even some players depart Nashville on Dec. 7. Let's do that now. 

1. Will Shohei Ohtani find a new home?

Ohtani's free agency is of course the biggest story of the winter, and it's possible we'll soon know where he'll be landing for 2024 and (probably) beyond. Ohtani, a two-time American League MVP, is the best and most famous baseball player in the world, and he's just 28 years of age, which is young as top-line free agents go. His unprecedented excellence at the plate and on the mound coupled with his star power mean he's going to sign the largest contract in MLB history, probably in excess of $500 million (assuming he doesn't opt for a one-year pact and re-enter the market next offseason). If Ohtani weren't limited to hitting only in 2024 as he recovers from a procedure to address a UCL tear in his pitching elbow, then the eventual figure would surely be even higher. Barring setbacks, though, Ohtani's new employer will be getting him in his entire two-splendor starting in 2025. 

Speaking of Ohtani's new employer and the possibility that we'll learn who that is while everyone's in Nashville, informed speculation is our guide. Said informed speculation has it that high-payroll current or aspiring contenders like the Dodgers, Rangers, Cubs, Giants, Mets, Red Sox, and Yankees will be foremost among the clubs trying to land the superduperstar. Maybe one will rise above the fray during the Winter Meetings. 

2. Will the posted free agents from Japan sign?

What would otherwise be a somewhat uninspiring crop of non-Ohtani domestic free agents is buoyed by the incoming arms from Japan. The two leading lights are hurlers Yoshinobu Yamamoto and Shota Imanaga. Yamamoto in particular will be a coveted hurler, as the right-hander combines ace-grade stuff and results with the fact that he's just 25 years of age. Coming into the offseason, we ranked Yamamoto as the No. 2 available free agent behind only, yes, Mr. Ohtani. The implication is that Yamamoto is indeed the best starting pitcher on the market this winter, a category that includes reigning NL Cy Young winner Blake Snell and the already-spoken-for Aaron Nola (Phillies) and Sonny Gray (Cardinals). 

As for Imanaga, he checked in at No. 42 on our list. Here's part of what we wrote about the 30-year-old port-sider

Imanaga, previously part of the Yokohama DeNA BayStars rotation, loves his low-90s fastball. He threw it around 60% of the time last season, all the while posting a usage rate above 15% on just one other offering, his slider. Imanaga relies on coercing outside-the-zone swings on his heater, something he did to great effect in Japan. It's to be seen if their American counterparts give pursuit as often. Imanaga generated close to 40% whiffs on his slider, and he may need to balance his arsenal more to be effective as a MLB starter.

Plenty of teams are in need of help in the middle of the rotation, and Imanaga figures to fit that particular bill. 

By way of reminder, NPB teams that post players for MLB consideration are entitled to a "posting fee" if those players sign with a U.S. major-league team. Here's how that system presently works: 

  • Contract worth less than $25 million: 20% of contract value
  • Contract worth $25 million to $50 million: $5 million plus 17.5% of amount over $25 million
  • Contract worth more than $50 million: $9.275 million plus 15% of amount over $50 million

Both Yamamoto and Imanaga figure to clear $50 million in total contract value, and in Yamamoto's case he'll almost certainly top $200 million with some degree of ease. 

As for the Winter Meetings, the posting system permits 45 days to strike a deal, and the clock is already ticking for both. There's no real urgency yet, but these meetings provide a fitting opportunity to get something down or, failing that, lay the groundwork for a deal soon after. In Yamamoto's case, he has until Jan. 4 to sign a contract, while Imanaga has until Jan. 11. 

The market for Yamamoto will be particularly heated. The Mets may be the favorites, but any number of clubs like the Dodgers, Cubs, Yankees, Giants, Phillies, Cardinals, Red Sox and others should be at least somewhat in the mix. Regardless of whether he signs at the Winter Meetings or not, Yamamoto's name will be bandied about quite heavily across those days. 

3. What about the other big stateside free agents?

Notably, we saw two premium free agents – the aforementioned No. 5-ranked Nola and No. 12-ranked Gray – go off the board before we even got to December. That's cause to suspect things will move quickly this offseason, and that, in turn, is cause to suspect some notable names will sign in Nashville. In addition to No. 1 Ohtani and No. 2 Yamamoto, seven other members of our top 10 free agents are still up for grabs. Those are:

  • No. 3 Cody Bellinger, CF/1B
  • No. 4 Matt Chapman, 3B
  • No. 6 Blake Snell, LHP
  • No. 7 Eduardo Rodriguez, LHP
  • No. 8 Marcus Stroman, RHP
  • No. 9 Lucas Giolito, RHP
  • No. 10 Jordan Montgomery, LHP

That's a lot of headline-grabbers, and some of them will surely, you know, grab headlines before the party in Nashville breaks up. Given the activity we've already seen on the starting-pitching front, some of those arms could be snatched up very soon. 

4. Will the Yankees swing a deal with the Padres for Juan Soto?

The Padres, after running one of the largest payrolls in MLB last season, are said to be looking to shed salary commitments for 2024. That's led to the expectation that they'll look to trade Juan Soto, who's in line for a salary of more than $30 million in his final year of arbitration/walk year. The Yankees badly need to improve the lineup around Aaron Judge, GM Brian Cashman has stated he wants to add more than one outfielder this winter, and they of course have vast resources. For those reasons, the Yankees are believed to be the frontrunners to land Soto should the Padres decide to move him.

While Soto would be a DH in a perfect world, Giancarlo Stanton is likely lodged in the role for the Yankees. That said, Soto's elite on-base skills and strong power numbers from the left side would be the perfect complement to Judge in the Yankee lineup. He is, after all, a 25-year-old who boasts a career slash line of .284/.421/.524 and for that career has averaged 133 walks and 33 home runs per 162 games played. Throw out the COVID-abbreviated 2020 campaign, and Soto since 2019 has averaged 154 games played per season, so he's also a durable sort. He'd greatly improve the Yankees' fortunes in 2024, and they have more than enough resources to sign him to a record-breaking extension or, if he's committed to testing the market next winter, bring back as a free agent. 

He checks a lot of boxes for New York, and if the Padres (unwisely) decide to move him then Cashman figures to be first in line. Such a deal could happen soon, as the two sides have reportedly advanced to the "discussing specific names" stage of talks

5. Will any other blockbuster trades go down?

On the non-Soto trade front, things are plenty active, so don't make the mistake of thinking he's the only marquee name potentially on the block. Specifically, a number of frontline starting pitchers may be available in trade. Those include Dylan Cease of the White Sox (the Braves have been heavily linked), Corbin Burnes of the Brewers, Tyler Glasnow of the Rays, and Shane Bieber of the Guardians. Elsewhere, Pete Alonso of the Mets and Bo Bichette of the Blue Jays will be the subjects of speculation, but in their cases deals seem less likely. What does seem likely is that one or more of those aces above will be changing addresses during the Winter Meetings. 

Now with those pressing questions posed, let's keep one eye on the proceedings in Nashville while otherwise warming ourselves by the coils of the hot stove.