Baseball’s annual winter meetings begin Sunday with what should be a captivating Hall of Fame announcement.
The intrigue should rise to full throttle Monday through Wednesday as the potential for blockbuster trades and record free-agent signings seem ripe this year.
Teams can make moves throughout the winter, but it’s been relatively slow so far. That will change in the next few days when conversations heat up, and players and teams attempt to have landing places set by the holidays.
Here are five developments to monitor at this year’s winter meetings in Nashville:
When, where and for how much does Shohei Ohtani sign?
Nothing else is more significant in the game right now. Baseball’s only two-way superstar is a free agent, and he is expected to claim the largest payday in the history of the sport’s open market.
There have been only faint whispers so far about his plans, and that is by design. Ohtani’s agent, Nez Balelo of CAA, is one of the most powerful in the game, but he prefers to keep a quiet profile when negotiating, and teams seem to respect that.
So, don’t expect much leaking or histrionics on this one. And I don’t expect it to drag out, either. That’s not Balelo’s history. Besides, Ohtani is the biggest domino this year and losing teams will want to know quickly that they are out, so they can pivot to other possibilities.
Deals this big take time; therefore, we may not know until later in December. Still, it wouldn’t be surprising if this is resolved in the upcoming week.
My guess is Ohtani remains on the West Coast with the Los Angeles Dodgers, San Francisco Giants and Seattle Mariners as worthy suitors. I don’t think he crosses the $500 million threshold because he won’t be able to pitch for at least a season, but others have speculated that number is within reach.
What do the Milwaukee Brewers do?
In all my years of covering MLB, I don’t think I’ve ever asked that question. No disrespect to the fine folks of Milwaukee, but rarely has their franchise been a market changer.
They have that opportunity this year. The Brewers won the NL Central by nine games in 2023 and made it to the postseason for the fifth time in six seasons. They could be the team to beat again in the division with a couple of tweaks and some good health.
But venerable manager Craig Counsell jumped ship for the rival Chicago Cubs and the Brewers non-tendered one of the best pitchers in franchise history, Brandon Woodruff, who likely won’t play in 2024 as he recovers from shoulder surgery.
If the Brewers want to go all in for a rebuild, they have three dynamic trade chips in 2021 NL Cy Young winner Corbin Burnes, slugging shortstop Willie Adames and two-time All Star closer Devin Williams.
Burnes and Adames are free agents at the end of 2024 and Williams after the 2025 season. If Milwaukee sells, it could acquire a truckload of prospects for the future. And teams would line up for that trio.
Related: MLB offseason free-agent trend: Giving love and money to old starters
Where does Yoshinobu Yamamoto land?
This free-agent pitching class includes reigning NL Cy Young Award winner Blake Snell and postseason hero Jordan Montgomery. Yet the consolation prize for missing out on Ohtani is another Japanese product.
Yamamoto is only 25 and he has won the last three Japanese Pacific League MVPs and the last three Sawamura Awards, Nippon Professional Baseball’s Cy Young equivalent. Yamamoto is a strike thrower with four above-average pitches, including a mid-90s fastball and a devastating splitter.
Yamamoto will almost certainly break the financial record for a Japanese free agent player entering MLB, set in 2014 by Masahiro Tanaka, who signed with the New York Yankees for $155 million.
The right-hander is expected to reach a rarified air for pitchers and command more than $200 million, plus a significant posting fee to his NPB team, the Orix Buffaloes. A $200 million deal would be approximately $32 million more to Orix.
One interesting note: A deal must be made by Jan. 4, so a decision is looming and that could prime serious talks next week. I still feel a New York team will be the highest bidder here, but again, clubs that can’t get Ohtani may up their game for Yamamoto.
Related: Looking at the 10 most intriguing non-tendered players who can help MLB teams
Will a superstar(s) be dealt during the MLB winter meetings?
I think so. Or shortly after that. The previously mentioned Burnes is a distinct possibility and other intriguing arms could be moved, such as Cleveland’s Shane Bieber, Tampa Bay’s Tyler Glasnow and Dylan Cease of the Chicago White Sox. The biggest fish to be sent elsewhere, though, might be San Diego outfielder Juan Soto, a free agent after 2024.
The Padres traded for Soto and Josh Bell in August 2022, sending six players, including CJ Abrams, MacKenzie Gore and stud prospect James Wood to the Washington Nationals.
Soto was supposed to be the Padres’ missing World Series piece, but they still haven’t reached that destination. Now, Soto, who turned 25 in October, could be on the move again in his walk year.
He started slowly in 2023 but ultimately posted a 5.5 WAR and a .930 OPS. He may be the best player available on the trade block since … Soto in 2022. If the Yankees indeed want to make a splash, here’s the guy.
Related: 3 ideal Juan Soto trade scenarios, including the New York Yankees
Which managerial great – or four – get the call to Cooperstown?
The first piece of official business in Nashville will be the announcement Sunday about which of the eight members on the non-players Contemporary Baseball Era Committee ballot will be inducted into the National Baseball Hall of Fame in 2024.
Four of the candidates are managers who have won World Series titles – Cito Gaston, Davey Johnson, Jim Leyland and Lou Piniella – and I believe all four should be in Cooperstown. I’m not on the 16-person panel – a candidate needs 12 votes for induction – but I wouldn’t say no to any of those four.
If I had to choose only one, it would be Leyland, who managed 22 seasons for four teams, took three to a total of eight playoff appearances and won the 1997 World Series with the Florida Marlins.
I’d also heavily endorse former general manager Hank Peters, who helped retool the Baltimore Orioles organization in the mid-1970s and the Cleveland Indians in the late 1980s, and former National League president Bill White, who was a trailblazer and had three distinct baseball careers: player, broadcaster and executive.
Also on the ballot are umpires Joe West and Ed Montague. All eight won’t get in, meaning some worthy candidates will strike out this time. But I’m curious to see which ones get the highly anticipated call.
Related: One move — signing, trade, hold the line — each National League team should make this offseason
Dan Connolly is an MLB Insider for Sportsnaut. Follow him on Twitter.