The Chicago Cubs will head into the winter meetings hoping to make some improvements to help get the team over the hump in the National League. However, they have some looming problems.

While it was an excellent season for the Cubs in 2025, it felt like it could have been more. This was a team that made a massive splash last winter to acquire star outfielder Kyle Tucker at a costly price. A move like that from the franchise was bold, but what they did or didn’t do afterwards was surprising.

At the trade deadline, this was a team that had a massive need in the starting rotation. The franchise didn’t adequately address that need, and it contributed to them being eliminated from the postseason.

This winter, as the team waits to see what happens with Tucker in free agency, they need to think about potential ways to replace that production if he does leave. That is going to be no easy task, and even if Tucker comes back, the team still needs to find ways to improve.

Buster Olney of ESPN recently wrote about what some of the top contenders need to do to improve this offseason. For the Cubs, it was to simply add “more.”

Cubs’ Biggest Priority Is That The Team Need To Be Aggressive

Even though it was nice to see the playoff drought snapped in 2025, Chicago still felt a bit off from being a real contender last year. With the potential loss of a star player, the Cubs will have some good internal options, thanks to their deep farm system, to help replace him, but they will need to look for some external help as well.

Chicago has unfortunately begun to develop a reputation for not spending when it needs to, and that is a problem. If, but more likely when, the team does lose Tucker, it will be because they couldn’t afford him. Considering what the team gave up to get him and the fact that it was just a one-year rental without an NLCS or World Series appearance, the move can be seen as a failure.

Now, with some uncertainties surrounding their star, the team certainly has to find a way to do more. Losing Tucker seems reasonably likely, and the franchise needs to be prepared for it. Whether it be upgrading the lineup, rotation, or bullpen, Chicago needs to get better with or without their star returning.

Overall, the Cubs are a team that undoubtedly needs to do more.