Cubs Under Pressure As Bregman Pursuit Could Impact Another Key Target

While the Chicago Cubs' front office has been notoriously stubborn in offering big contracts to top free agents in the past, various reports this offseason have suggested that the team is willing to make a major splash this winter.

A look at the Cubs' current roster suggests that this splash would perhaps be best spent on either an elite reliever or a frontline starting pitcher. However, now that Pete Fairbanks has signed with the Miami Marlins, there are no quality closers available on the market any longer.

And while several ace-caliber arms are still unsigned, some reports suggest that the Cubs are most interested in All-Star third baseman Alex Bregman.

Jed Hoyer and the rest of the Cubs' brass have always been interested in Bregman, as they offered him a lucrative deal in free agency last offseason before he signed with the Boston Red Sox. However, their potential pursuit of Bregman becomes clouded, given the presence of another compelling free agent third baseman.

Alex Bregman Could Alter Another Potential Cubs Target

Japanese third baseman Kazuma Okamoto has been posted by his NPB team and must sign with an MLB club before January 2. Given his success overseas (he has 247 home runs in 11 seasons), Okamoto should command a high price in free agency.

New York Post insider Jon Heyman conveyed how these two players impact each other's market (and how the Cubs might be caught between) during a December 22 live stream with Bleacher Report.

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

"I've got six teams potentially for Okamoto... I've got the Angels, the Pirates, the Red Sox, Blue Jays, Cubs, and Diamondbacks," Heyman said. "Now, you'll notice that a lot of those teams are Bregman teams, so I think the Bregman situation needs to be clarified, and probably will be before Okamoto's [posting] expires, and that's on, I believe, January 2nd.

He later added, "Again, those last four teams, Boston, Toronto, Cubs, and Arizona, all teams that are looking at Bregman, as well. So it will be interesting to see, once Bregman signs, we're gonna lose one of those teams."

In other words, since Okamoto needs to sign before January 2, the Cubs might need to decide whether they want to try to sign him or Bregman in the next week.

If they want to wait past January 2 before giving Bregman their final offer, he still might end up elsewhere, and Okamoto will already be with another team.

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