MLB Insider's Alex Bregman Update Raises Red Flag For Cubs

Many Chicago Cubs fans are holding out hope that their club will sign star third baseman Alex Bregman in free agency this winter.

Bregman is one of the three best remaining free agent hitters available. And given that the other two are former Cubs, Kyle Tucker and Cody Bellinger (both of whom primarily play in the outfield, where the Cubs are already loaded with talent), Bregman is who makes the most sense for Jed Hoyer to pursue if he wants to sign a quality bat.

That being said, Bregman is far from a perfect fit, if only because of the Cubs' current infield situation. Signing him would likely force Matt Shaw to second base, which would all but mean incumbent second baseman Nico Hoerner would either get traded or surely wouldn't re-sign with Chicago after next season, when he becomes a free agent.

Still, there's an argument to be made that the Cubs should focus on signing Bregman now and worry about the rest of their roster later, given that the three-time All-Star and two-time World Series winner is a premier talent who would surely increase Chicago's chances of winning their first championship since 2016.

Why latest Alex Bregman buzz isn’t trending toward Cubs

The free agency market has been relatively quiet over the holidays, but it is sure to heat up in the first month of 2026. However, if the race to sign Bregman is picking up steam, it doesn't seem that the Cubs are keeping pace.

Boston Red Sox third baseman Alex Bregman on September 7, 2025 — Red Sox third baseman Alex Bregman against the Arizona Diamondbacks at Chase Field. | Mark J. Rebilas-Imagn Images

This was conveyed by a January 1 article from MLB.com's Mark Feinsand, who wrote, "Sources believe the Blue Jays and Diamondbacks may be the two most aggressive clubs in the hunt for Bregman, though a Red Sox reunion remains a possibility."

He also noted that the Cubs and the Tigers have been connected to Bregman at various points in this offseason. Yet, the fact that Chicago isn't being considered one of the more aggressive teams to secure Bregman's services does not bode well for their chances of getting him in free agency.

Teams that have been connected to Alex Bregman this offseason, per @Feinsand:

Blue Jays
Diamondbacks
Cubs
Red Sox
Tigers

“Sources believe the Blue Jays and Diamondbacks may be the two most aggressive clubs in the hunt for Bregman, though a Red Sox reunion remains a possibility” pic.twitter.com/xmRcYxzWO8
— SleeperMLB (@SleeperMLB) January 2, 2026

From a roster perspective, it would seemingly make more sense for the Cubs to sign one of the frontline starting pitchers available, such as Framber Valdez, Ranger Suarez, or Zac Gallen.

What's for sure is that many Cubs fans will be left feeling frustrated if Chicago's biggest free agency move is signing Phil Maton in an offseason where they lost Kyle Tucker.

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