Major League Baseball’s Winter Meetings, the annual convergence of the industry’s movers and shakers, will get underway on Dec. 9 in Dallas. The event tends to serve as a hub for increased offseason activity, in large part because it’s one of the few occasions where top executives and agents are gathered in the same vicinity with nothing better to do than attend to the business at hand.
With that in mind, we here at CBS Sports felt it would be wise to preview the Winter Meetings by asking (and attempting to answer) seven industry-wide questions. Some are assured resolutions during the Winter Meetings, others are less certain.
All together, they’ll shape if these Winter Meetings live up to the hype.
1. Will Soto sign?
Our best guess is that Juan Soto, the No. 1 player on CBS Sports’ top 50 free agents list, will have picked his next team before the Winter Meetings conclude. That isn’t based on inside info. Rather, it stems from recent precedent.
In each of the last two offseasons, the top overall free agent has made up their minds within the first two weeks of December. Aaron Judge elected to rejoin the New York Yankees on Dec. 7, 2022. Nearly a year to the day later, Shohei Ohtani decided to sign with the Los Angeles Dodgers on Dec. 9, 2023.
Maybe Soto’s free-agent foray lingers beyond those dates, but we have a hard time envisioning him waiting much longer than that to make his pick.
2. Might aces fall into place?
Two-time Cy Young Award winner Blake Snell chose his new home before Thanksgiving, agreeing to a five-year deal with the Los Angeles Dodgers worth $182 million that will keep him in his familiar haunt, the National League West.
With Snell establishing the market, it seems like only a matter of time before right-hander Corbin Burnes and fellow lefty Max Fried find deals of their own.
Additionally, don’t sleep on the chances of the Chicago White Sox ramping up efforts to trade Garrett Crochet. He was viewed as the top pitcher on the market heading into the 2024 deadline and should appeal to teams seeking a budget-friendly front-end starter.
3. What of the infield?
Elsewhere on the diamond, free-agent infielders Alex Bregman and Willy Adames should be inching closer to finding lucrative contracts of their own.
One team to watch on this front? The Houston Astros. They’re known to have interest in either retaining Bregman, a franchise mainstay, or, shy of that, installing Adames as Bregman’s successor. Houston, then, could cause the first domino to fall.
4. Will Sasaki get posted?
Don’t look for Japanese right-hander Roki Sasaki to ink an agreement during the Winter Meetings. Indeed, he’s not expected to choose a suitor until after Jan. 15, when a new international amateur signing period opens and teams have more money to spend. In fact, he and his representatives aren’t even supposed to be talking to teams before he’s officially posted.
Still, we may gain some clarity on Sasaki’s exact timeline — if only in the form of the Chiba Lotte Marines posting him and opening his negotiating window.
5. Will the Hall of Fame gain new members?
The Classic Baseball Era Committee will meet on Sunday to determine if any of the eight candidates put in front of them (seven players and a manager) merit entrance into Cooperstown. Dick Allen, Ken Boyer, John Donaldson, Steve Garvey, Vic Harris, Tommy John, Dave Parker, and Luis Tiant are all on the ballot.
Their fates, meanwhile, will be determined by a 16-person board that includes Hall of Famers Paul Molitor, Eddie Murray, Tony Pérez, Lee Smith, Ozzie Smith, and Joe Torre, as well as executives Sandy Alderson, Terry McGuirk, Dayton Moore, Arte Moreno, and Brian Sabean.
The Classic Baseball Era ballot was determined by a group of 10 baseball historians.
6. Who will win the draft lottery?
MLB will announce the results of the latest draft lottery on Dec. 10.
Four teams have at least a 10% shot at laying claim to the top overall pick: the Colorado Rockies (22.45% chance), Miami Marlins (22.45%), Los Angeles Angels (17.96%), and Washington Nationals (10.2%).
The Chicago White Sox and Athletics, two of the four worst teams in MLB last season, are both ineligible for the lottery. The White Sox are eliminated because they had a lottery pick last season and are a revenue-sharing payor; the Athletics because they’re a revenue-sharing recipient who held lottery picks in both the 2023 and 2024 drafts.
Keep in mind that the Cleveland Guardians won last year’s lottery despite having just a 2% chance at the top spot. They subsequently used that pick to select Oregon State second baseman Travis Bazzana.
7. Will the Rule 5 Draft produce another gem?
Speaking of drafts, MLB will also host this year’s Rule 5 Draft on Dec. 11.
For those unfamiliar with the concept, the Rule 5 Draft is essentially a mechanism that combats talent-hoarding by forcing teams to add their best youngsters to their 40-player rosters after a certain amount of service time. The players left unprotected can then be selected by other clubs, albeit with the caveat that the team must then keep the player on their active big-league roster for the duration of the ensuing season.
In the past, such individuals as Roberto Clemente, Johan Santana, and Josh Hamilton have been selected through the Rule 5 Draft.
The Chicago White Sox have secured the top selection in the upcoming Rule 5 Draft. This gives them the opportunity to choose a promising player from another team’s minor league system to add to their roster. The Rule 5 Draft is a chance for teams to find hidden talent and potentially uncover a future star. The White Sox will have the first pick, and their selection could make a significant impact on their team for the upcoming season.