What Is Biggest Question for Chicago Cubs Heading Into Winter Meetings?

The Chicago Cubs are heading into the Winter Meetings as a team to watch, as they could be looking to either improve in free agency or via trade.

As the Winter Meetings get closer, the Cubs are likely going to be very active during this time to try and improve their team.

Even though Chicago finished over .500 in 2024, there is still some work to do in order to make them a contender. Leading up to the Winter Meetings, the Cubs have been one of the more active teams so far this offseason. However, they are likely far from done.

With some needs still in the bullpen, starting rotation, and lineup, Chicago could look to make upgrades in multiple ways.

Jordan Bastian of MLB.com recently spoke about the biggest question heading into the Winter Meetings for the Cubs. He highlighted what the future might hold this offseason for Cody Bellinger.

The working theory entering the offseason was that Bellinger would opt out of his deal and hit the open market. Instead, the veteran outfielder exercised his $27.5 million player option for ‘25.

At the GM Meetings in November, Cubs president of baseball operations Jed Hoyer said: “Anytime a really good player decides to stay with you, that’s good news.” True, but that decision also limited the front office’s roster and financial flexibility to address the offense. Now, 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. That said, it makes sense for the Cubs to at least explore the market for Bellinger, especially with teams that may miss out on signing Soto.

It was certainly a surprise that Bellinger elected to opt in for the season, and while that could work out for Chicago, it did limit them financially this offseason. The Cubs were going to be looking for a power bat in free agency, but with over $25 million going to Bellinger this coming season, it seems unlikely that they will spend big.

However, with him opting out, it does mean that Chicago has control and could look to move him. With another potential option for next season, it does make his trade value a hard one to figure out, but he is a very talented player that could help teams.

While the Cubs are hoping to contend in 2025, they have a lot of young talent that they are trying to find at-bats for in the majors. By trading the slugger, it would not only free up money to spend this offseason, but it could create some opportunities for younger players.