Chicago Cubs had a Zoom meeting with massive free agent ahead of 2025 Winter Meetings

The Chicago Cubs are in a position where the team has some glaring holes they need to fill the offseason. While there have been some major free agent signings already happening, there are some premier players still on the board. In fact, a report came out that the Cubbies have been in contact with one of them. Let’s take a closer look at who the free agent is and what this possible signing would mean for the Cubs heading into the 2026 season.

Chicago Cubs had Zoom meeting with Alex Bregman

Fansided’s Robert Murray has reported that the Chicago Cubs held a Zoom meeting with free agent third baseman Alex Bregman a few weeks ago. They are not the only team to do so, as he has had “several” meetings with teams already. This at least helps confirm the reported interest that the team has been linked to Bregman this offseason. Of course, this is not the only time the two sides have communicated as they made an offer last offseason to him with a four-year, $115 million contract while having opt-outs following Years 2 and 3 of the contract. Bregman would choose to sign a three-year, $120 million contract with the Boston Red Sox instead and opt out following the first season.

Bregman, 31, has shown to be an outstanding third baseman defensively while hitting at an incredible level. He finished the 2025 season with a .821 OPS while hitting 18 home runs, 62 RBI, 64 runs scored, and a 51:70 walk-to-strikeout ratio in 114 games. He is coming off a 2024 season with the Houston Astros where he won the AL Gold Glove as well, proving he is still an incredible player.

What would Alex Bregman signing with the Chicago Cubs mean for the roster?

The possible signing of Alex Bregman would give some options for general manager Jed Hoyer to do with the roster. This would likely signal the end of Matt Shaw’s tenure with the team, as he could be traded for pitching during the offseason. The lineup would essentially move one former Astro player in Kyle Tucker for another and fills some need. Only shortstop Dansby Swanson is under a guaranteed contract in the infield following the 2026 season, so this is a chance to solidify the left side of the infield.

It also would help allow Hoyer to sign groundball pitchers as Bregman is an elite defender. This move could be a strong addition and would have ripple effects throughout the roster and Major League Baseball.

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