Cubs Finally Connected to Free Agent Hitter to Upgrade Lineup

He may not necessarily be the top free agent hitter on your offseason wishlist nor mine, but it’s good to see the Chicago Cubs finally connected to someone that could theoretically upgrade the lineup heading into 2026. All-Star outfielder Kyle Tucker will sign somewhere else this winter and while it’ll be a tough task to replace his production the Cubs have to find a way in order to sure up their offense next season.

We’ve discussed the possibility of the Cubs simply relying on Moises Ballesteros and Owen Caissie to take over the share of plate appearances left vacant by Tucker’s foreseeable departure and it just doesn’t make sense. You can’t lose a guy like Tucker, who in a down year for him still posted a 136 wRC+ and had a 143 OPS+ in 2025, and not bring in an established hitter.

And with that being said The Athletic’s Patrick Mooney and Sahadev Sharma are reporting that the Cubs are indeed looking at a bat in free agency and it is one of their previous targets Alex Bregman.

Yes, improving the pitching staff both in the bullpen and starting rotation, remain the top priority, but it is certainly intriguing to see the renewed interest in Bregman. Last offseason the Cubs hung around in talks for the two-time World Series champion and three-time All-Star, but were ultimately left empty-handed. Bregman signed with the Boston Red Sox, declining the Cubs’ four-year, $115 million offer that included a player opt out after the second and third year of the contract.

Bregman became a free agent this offseason after opting out of his three-year, $120 million deal with the Red Sox. He was en route to a monster season in 2025, posting a slash line of .299/.385/.553, with 11 home runs in 226 plate appearances before a quad injury sidelined Bregman for seven weeks. This is where it gets tricky because what do you trust, Bregman’s strong track record at the plate and on defense, or do you get worried that he’ll be in his age-32 season next year and was very much average offensively once he returned from his injury this past season with the Red Sox?

The Cubs obviously believe in the fit as they’re reportedly returning to Bregman this offseason and it is important to note that ownership approved Jed Hoyer’s offer to the third baseman back in February. You’d think that if the team is revisiting talks with Bregman, then there should be no issues committing to another sizable offer.

However, as we’ve seen with a few contracts already signed by other Cubs targets, the team isn’t willing to include deferred money in their offers. Will that come into play with Bregman? You’d think so, which means the Cubs can’t afford to come below Bregman’s asking price if they’re serious about signing him.

We’ll continue to monitor this storyline, but for me the biggest point remains that a free agent hitter is finally on the Cubs’ radar. Hopefully, the team will explore more options because replacing Tucker will not be easy.