MLB Winter Meetings are in full swing, and reaching the halfway point, the league has already witnessed several major deals go down.
With all of baseball’s front office executives together until Friday, and pressure building to get deals done, expect to see some major announcements over the next 72 hours and beyond.
Chicago Cubs fans should also expect the team to get in on the action, as the team has reported interest in a number of free agents still available. Here’s the latest Cubs news and stories to catch up on.
Cubs Notes
Jed Hoyer’s statement on Matt Shaw speaks volumes – Cubs president of baseball operations, Jed Hoyer, was seemingly perplexed by Matt Shaw’s name being mentioned as trade bait. Per ESPN’s Jesse Rogers, Hoyer said, “I’ve been surprised by the number of media reports that link us to different guys. There is zero lack of confidence in Matt. I would say the opposite.”
Matt Shaw | Matt Marton-Imagn Images
Cubs Manager Craig Counsell also commented on Shaw at the Winter Meetings yesterday, admitting that his first season “kind of kicked him,” and “knocked him down a little bit.” However, Counsell also showed faith in Shaw, saying, “(He’s) just getting better defensively. He’s gonna be one of the better third basemen … Matt’s gonna be an important part of the 2026 Cubs team.”
Cubs and Alex Bregman had Zoom meeting – According to Robert Murray of FanSided, the Cubs and Bregman had a Zoom call a few weeks ago. Murray also reports Bregman met with “several” other teams.
The Cubs found themselves in a bidding war for Bregman last season, ultimately losing out to the Red Sox. And while the team has been linked to Bregman throughout this offseason, Jed Hoyer’s statements regarding Matt Shaw raise questions as to how serious the team’s interest might be.
Alex Bregman | Brad Penner-Imagn Images
Craig Counsell admits what Cubs got wrong in 2025 – The Cubs boss admitted the team was surprised by their relief corps last season, saying “What we thought about the bullpen going into the season, we were wrong. We were pretty wrong on it. We ended up pitching pretty well but at the start of the season, it wasn’t the guys we expected to do it.”
Counsell also discussed where the bullpen currently sits for 2026: “We’ve got a lot of work to do there. That’s probably the one place where we lost; we had a lot of free agents in that group that we lost. So we’ve got a lot of work to do, replacing and fortifying that group.”
This past season, the @Cubs advanced to the NLDS for the first time since 2017!
Craig Counsell discusses his second season as manager and how he looks to fortify their bullpen this offseason.
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— MLB Network (@MLBNetwork) December 9, 2025
Zac Gallen trolls Cubs free agency signing report – For a short time on December 6, baseball fans through the Cubs had acquired one of the best starting pitchers on the market, thanks to a premature report by insider Bob Nightengale. The story went viral on social media, but the report was quickly refuted, and Nightengale himself updated his original tweet to reflect that no deal was done.
Gallen, who was actually getting married that day, made light of the situation in his own social media post, sharing a picture of his and his wife’s hands with wedding rings alongside the caption, “The only contract signed this weekend”
Cubs interest in free agent closer Pete Fairbanks revealed – In a December 9 article by Sahadev Sharma, he noted the Cubs have “kept tabs on” Fairbanks throughout free agency. Fairbanks, who has been with the Tampa Bay Rays since 2019, became a free agent after the team declined his team options for 2026. In 2025, he produced a 2.83 ERA and secured 27 saves in 32 opportunities.
Cubs top prospect Owen Caissie to represent Canada in 2026 – Caissie will join Team Canada for the 2026 World Baseball Classic next year. He played in three of Canada’s four games in 2023, getting three hits in 13 at-bats. While Canada has participated in all five WBC events, it’s never made it out of the group stage. Teammates Pete Crow-Armstrong and Matthew Boyd will represent Team USA.
Owen Caissie | Patrick Gorski-Imagn Images
Cubs could lose Brad Keller to the New York Yankees – According to Joel Sherman of the New York Post, the Yankees are one of the teams keeping an eye on Keller, and they are reportedly keen to use him as both a reliever and starter.
Keller had a stellar season for the Cubs in 2025, posting a 2.07 ERA, 0.962 WHIP, and 1.4 bWAR with the best strikeout rate of his career. The loss of Keller would be a significant blow to the Cubs, so hopefully Jed Hoyer and Keller are making progress in negotiations.
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