Cubs Should Pursue This Talented Free Agent To Avoid Making The Same Mistake Twice

With the winter meetings right around the corner for the Chicago Cubs, the team will be focused on trying to make some improvements in order to build on what they accomplished in 2025.

While it was a successful season for the Cubs last year, it felt like they could have accomplished more if they had remained aggressive in making improvements. The decision to trade for Kyle Tucker was one that changed the direction of the franchise and was a significant reason why they accomplished what they did.

However, while Tucker was a great addition, more was needed for the team. Both in the offseason and at the trade deadline, the team didn’t go all-in, knowing that their new star slugger could have very well been a rental. That is starting to look more likely with Chicago not being mentioned frequently as a landing spot for Tucker this winter.

If they do end up losing the All-Star to free agency, there are some other options available that they could pursue. One player is someone who they arguably should have signed last offseason.

Buster Olney of ESPN recently wrote about Alex Bregman still being a good fit for the Cubs, like he was last winter. However, he was too expensive for Chicago then, and that price tag has likely gone up.

Cubs Need a Splash

After the addition of Tucker and the team seemingly looking to make a run, one position that was a significant question mark for the franchise was at third base. Matt Shaw was regarded as a top prospect, but with no experience in the Majors, he was handed the job on Opening Day.

Boston Red Sox third baseman Alex Bregman — Junfu Han / USA TODAY NETWORK via Imagn Images

That proved to be a mistake for the most part, with the talented slugger struggling for a good chunk of the year. Good production from third base was hard to come by, and the decision not to sign Bregman was likely regretted.

The talented slugger from the Houston Astros ended up signing a creative deal with the Boston Red Sox that allowed him to bet on himself to have a strong campaign, and that is precisely what he did. With it seemingly likely Tucker is going to leave (especially considering he recently toured the Blue Jays facility), adding a player of the caliber of Bregman would soften the blow.

It isn’t often that a team has a second chance at acquiring a talented player like Bregman, but that is the case for Chicago this winter. Adding the All-Star slugger would be an excellent move for the Cubs, especially if they lose Tucker.

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