Brett and Michael are back for the forty-third episode of the Bleacher Nation Cubs Podcast (Presented by Ankin Law)! With the offseason rolling along, the guys check in on the latest Cubs news, rumors, and roster questions as the front office continues shaping the team for 2026.

They discuss where things stand across the roster, what types of moves still feel likely in the coming weeks, and how the Cubs may be approaching the rest of the winter.

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Brett and Michael are back for the forty-second episode of the Bleacher Nation Cubs Podcast (Presented by Ankin Law)! It’s been a quiet Winter Meetings, but the Cubs have made another meaningful addition to the bullpen.

They break down Chicago’s signing of lefty Hoby Milner, a move that felt inevitable after last offseason’s near-miss. Milner profiles as an ideal fit for the middle innings, and paired with Phil Maton, represents a strong start to the Cubs’ bullpen rebuild.

The guys also talk about how quickly the closer market has dried up, with many top names already off the board, and what that means for the Cubs’ remaining relief plans.

Plus, the Alex Bregman rumor cycle continues—this time with word that Scott Boras has opened discussions with the Mariners—which naturally leads to more speculation about how the third-base market may shape up.

A special thank you to Ankin Law for sponsoring this podcast!

Visit Ankin Law's Website ➡️ ankinlaw.com

Read more Cubs coverage ➡️ bleachernation.com

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Brett and Michael are back for the forty-first episode of the Bleacher Nation Cubs Podcast (Presented by Ankin Law)! With the Winter Meetings a week away, the guys cover the latest Cubs news and rumors as the offseason slowly begins to take shape.

They talk about the Cubs’ minor league deal with infielder Scott Kingery, how it fits the team’s low-risk depth-building approach, and where things stand with potential extensions—particularly Pete Crow-Armstrong’s after his uneven rookie season.

The guys also discuss Kyle Tucker’s meeting with the Blue Jays, why the Cubs aren’t expected to be involved in those talks, and the expectation that bullpen additions are still coming soon.

Finally, they break down reports that the Cubs were in on Dylan Cease before backing out as the bidding passed $200 million, and what that says about the front office’s willingness to spend. Despite missing out, the Cubs appear poised to pursue other high-end arms such as Framber Valdez, Tatsuya Imai, Ranger Suárez, Michael King, and Zac Gallen as the market develops.

A special thank you to Ankin Law for sponsoring this podcast!

Visit Ankin Law's Website ➡️ ankinlaw.com

Read more Cubs coverage ➡️ bleachernation.com

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.