Chicago Cubs Winter Meetings 2024: Notable free agency, trade rumors to track

The crown jewel of Major League Baseball's offseason, the Winter Meetings, are to begin this week as baseball executives and players will convene in Dallas in a gathering that often lead to the impact moves of the winter being made.

The Winter Meetings have seen allure fade in recent offseasons as the drawn-out process of Shohei Ohtani's free agency and Yoshinobu Yamamoto's posting last winter led to most of baseball standing pat at the meetings last offseason. That isn't expected to be the case this week in Dallas.

Beginning with Juan Soto, the superstar outfielder is expected to reach a decision by the end of the Winter Meetings but latest reporting would suggest a decision could arrive within the next 24-48 hours. Once Soto signs, that should set the stage for what will be a very active week for Major League Baseball.

2024 MLB Winter Meetings: Dates, schedule, and everything Cubs fans need to know

The official dates of the Winter Meetings are December 9-12 but as executives arrive on Sunday, it's likely that there will be an uptick of rumors beginning on Sunday. Among the procedural events that will take place is the draft lottery, the Cubs have a less than 1% chance of landing the top pick.

In addition to the draft lottery, the Rule 5 draft will also be completed. The Cubs protected Owen Caissie earlier this offseason by adding him to the 40-man roster but outfield prospect Christian Franklin has been mentioned as a candidate to be selected.

What will the Cubs do at the MLB Winter Meetings this year?

Starting pitching remains at the center of the rumors involving the Cubs. While the Cubs have added Matthew Boyd to their rotation already, the team is believed to be aiming higher, eyeing a potential trade for Garrett Crochet or Luis Castillo.

Once Soto makes a decision, it's wide expected that a Cody Bellinger trade will be among the immediate moves made in the aftermath. It remains highly likely that Bellinger is not on the Cubs' roster by this time next week.

If the Cubs leave Dallas with no significant move made, that would be a mistake. While the Cubs won't make headlines with free-agent signings, they have the prospects to acquire any player available on the trade market.

Willy Adames signs with San Francisco Giants

Before the Winter Meetings even started, we saw a major free-agent signing: Former Milwaukee Brewers shortstop Willy Adames has reportedly signed a seven-year deal with the San Francisco Giants.

The Giants finally are able to land an impact free-agent after missing out on Shohei Ohtani and Aaron Judge in recent offseasons.

There was no connection between Adames and the Cubs this offseason outside of the fact that it was likely the shortstop would be leaving the National League Central. Similarly, the Giants were not among the teams believed to be involved in a potential trade for Cody Bellinger.

Nevertheless, the Adames' deal sets the stage for what should be an eventful week.

Juan Soto signs historic deal with New York Mets

On the eve of the official start of the Winter Meetings, Juan Soto signed the largest deal in professional sports history on Sunday.

With Soto off the market, the Cubs likely will step up their efforts to move Cody Bellinger. After missing out on bringing back Soto, the Yankees could look to Bellinger as a fallback option.

Chicago Cubs nearing deal with Carson Kelly

On the first day of the Winter Meetings, the Chicago Cubs are nearing a deal with veteran catcher Carson Kelly.

Kelly is a plus-grade defensive catcher, who allow the Cubs to have a timeshare at the position with Miguel Amaya. This setup would also allow top prospect Moises Ballesteros to serve as third catcher once he makes his Major League deal.

Mike Tauchman signs with the Chicago White Sox

Last month, there was some surprise that the Chicago Cubs non-tendered veteran outfielder Mike Tauchman. Tauchman had value to the Cubs as fourth outfielder but with Pete Crow-Armstrong, Kevin Alcantara, and Owen Caissie all figuring to be a part of the mix in 2025, Tauchman likely was going to be the odd man out.

Tauchman will be remaining in the city, however, as he has signed with the Chicago White Sox.

Stay clicked on this page throughout the Winter Meetings, and we will update it with the latest rumors, news, and moves from the week ahead.