What do the Cubs need to do at the Winter Meetings?
Jordan Bastian
@MLBastianThis story was excerpted from Jordan Bastian's Cubs Beat newsletter. To read the full newsletter, click here. And subscribe to get it regularly in your inbox.
CHICAGO -- The arrival of the Winter Meetings each December offers the chance for baseball’s Hot Stove to start sparking with activity. For the Cubs, they remain on the hunt for upgrades on multiple fronts and will look to use the upcoming gathering in Dallas to further that process.
“You’re always trying to be creative,” Cubs president of baseball operations Jed Hoyer said last month. “And I think there’s room for it this year.”
Let’s break down the Cubs’ situation ahead of the Winter Meetings:
Key events
• Sunday: Hall of Fame Classic Baseball Era Committee results released
• Tuesday: MLB Draft Lottery
• Wednesday: Rule 5 Draft
Club needs
Bullpen: The Cubs did not gather enough bullpen depth last offseason, leaving the team scrambling to find arms during the year as injuries and other issues mounted. So far this winter, Chicago has traded for Eli Morgan, claimed Rob Zastryzny and signed Phil Bickford (Minors deal). The Cubs will be looking to keep adding volume to the depth chart, while also possibly targeting an impact addition for the later innings.
Rotation: While the Cubs have a two-year agreement in place with lefty Matthew Boyd, that should not stop the front office from trying to find an additional arm for the rotation. Chicago will not be playing at the top of the free-agent market, but the team could still look at more cost-effective options (including via trade). The Cubs should also be among teams making a pitch to Roki Sasaki after he is posted (expected in January).
Catcher: The North Siders acquired Matt Thaiss from the Angels, but expect the team to keep an eye on potential upgrades behind the plate. If nothing pans out on this front, Thaiss could serve as the backup to Miguel Amaya, but there is still room for improvement.
Potential trade candidates
Expect to hear outfielder/first baseman Cody Bellinger’s name throughout the Winter Meetings as a possible trade chip, especially for teams that come up empty in a pursuit of free agent Juan Soto. Cubs second baseman Nico Hoerner (an elite defender with plus speed, the ability to play shortstop and an affordable contract running through ‘26) has also popped up in trade rumors already this winter. They top Chicago’s list of trade candidates, though the North Siders also have a deep farm system that could come into play.
Prospects to know
The first six players in that group have a chance to reach the Majors as soon as ‘25 (Alcántara already debuted down the stretch last year). The surplus of talent in Chicago’s system is not only a positive for the MLB depth chart, but could be helpful as the North Siders explore the trade market to tackle needs.
Rule 5 Draft
If the Cubs (who have made no Rule 5 selections in the MLB phase since 2020) roll the dice on a pick this year, chances are it would be a reliever. Given the North Siders’ need for bullpen depth, this is one avenue for trying to add another arm. That said, a Rule 5 pick has to remain on an active roster for the entire season (or be offered back to his former team). That layer of inflexibility could be a deterrent.
Burning question: Are the Cubs really considering a Bellinger trade?
Bellinger exercised his $27.5 million player option for ‘25, which was described as “good news” by Hoyer at the GM Meetings last month. True, but that decision also limited the front office’s roster and financial flexibility to address the offense this winter. Bellinger has another opt-out clause after next season ($25 million or a $5 million buyout for ‘26), adding a complicating factor to any trade talks. Even so, it makes sense for the Cubs to at least explore the market for Bellinger, if the team wants to consider alternatives to enhance the lineup.