Alex Bregman Market Moves In Cubs’ Favor After Latest Major Signing

The Chicago Cubs got a great update regarding their pursuit of Alex Bregman.

Aug 27, 2025; Baltimore, Maryland, USA; Boston Red Sox third baseman Alex Bregman (2) gestures on the field before the game between the Baltimore Orioles and the Boston Red Sox at Oriole Park at Camden Yards. Mandatory Credit: James A. Pittman-Imagn Images | James A. Pittman-Imagn Images

It has become clear that the Chicago Cubs are keen on signing star infielder Alex Bregman this offseason. In the past week alone, multiple insiders have conveyed that the Cubs are among the favorites to sign the three-time All-Star and two-time World Series champion.

On December 29, New York Post MLB insider Jon Heyman said during a live stream, "Bregman, it's the same teams: Boston, Cubs, Arizona, and Toronto. So we've got four teams. [Bregman is] certainly just waiting for that right deal, and we assume the right deal is probably at least five years if he can do it. Last year, he went for a shorter-term deal, opted out."

Heyman did later note that the Cubs would probably have to trade beloved second baseman Nico Hoerner for a Bregman acquisition to make sense. But the Cubs' continued interest shows that they appear eager to sign Bregman first, then figure out how their roster shakes out afterwards.

Sep 7, 2025; Phoenix, Arizona, USA; Boston Red Sox third baseman Alex Bregman against the Arizona Diamondbacks at Chase Field. Mandatory Credit: Mark J. Rebilas-Imagn Images | Mark J. Rebilas-Imagn Images

Toronto’s latest signing may open door for Cubs on Alex Bregman

What's for sure is that the Cubs received great news when it comes to Bregman's market on January 3, as news broke that the Toronto Blue Jays signed 29-year-old infielder Kazuma Okamoto. While Okamoto did make sense for the Cubs to pursue, their efforts were focused on Bregman instead.

And now, the fact that Toronto signed Okamoto almost certainly means that they're out on Bregman, as Okamoto will likely be manning third base for them. Therefore, the teams that are reportedly still in the running for Bregman just went from four to three.

MLB.com's Blue Jays beat writer Keegan Matheson confirmed this in a January 3 article by writing, "Given that Okamoto profiles best as a third baseman for the Blue Jays, this seems to lessen the appeal of Bregman to Toronto."

As the off-season begins to heat up here, a name The #Cubs could consider is Alex Bregman.

In '25:
-114 G
-118 H
-18 HR
-62 RBI
-.273 BA
-51 BB

If you're the Cubs, would you go after Bregman? pic.twitter.com/J9OW8OXbwl

— Just Another Year Chicago: Cubs (@JAYChi_Cubs) December 8, 2025

While Toronto potentially bowing out of the Bregman sweepstakes is undoubtedly good news for the Cubs, they still have stiff competition in signing the star third baseman. Bregman had a good 2025 season with the Red Sox and enjoyed his time there, and the appeal of living in Arizona year-round (as that's where half of MLB teams have their spring training) always makes the Diamondbacks an intriguing free agency destination for players.

Still, this is a step in the right direction for a Chicago team that has been quite quiet in free agency this offseason. Perhaps this Okamoto signing presents their perfect opportunity to pounce.

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