Brett and Michael are back for the forty-sixth episode of the Bleacher Nation Cubs Podcast (Presented by Ankin Law)! After a quick look back at the flurry of moves from the past couple of weeks, the guys zoom out to examine how the broader league landscape is taking shape—and what it means for the Cubs.

They discuss a busy stretch for the New York Mets, who have aggressively retooled their roster with multiple high-upside additions. While the Mets look formidable on paper, the guys debate whether the moves truly raise their floor or simply introduce more volatility—especially with Luis Robert Jr., whom they describe as a complete roll of the dice.

Attention then shifts to the Milwaukee Brewers, who completed a notable trade sending Freddy Peralta to New York. On one hand, the deal could make the NL Central more navigable for the Cubs in the short term. On the other, the Brewers’ long-term outlook remains strong, reinforcing their reputation as baseball’s ultimate “devil magic” organization.

Finally, the guys talk about how a busy January could jump-start the rest of the market—particularly for relievers—and whether the Cubs could still be involved in pitching talks as the offseason continues.

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Brett and Michael are back for the forty-fifth episode of the Bleacher Nation Cubs Podcast (Presented by Ankin Law), and it’s been a very busy week.

The Cubs finally made their biggest move of the offseason—and one of the biggest in franchise history—signing third baseman Alex Bregman to a five-year, $175 million deal. With deferrals lowering the luxury tax hit, the Cubs pushed decisively into their contention window, adding a true middle-of-the-order presence and locking down third base. The guys discuss why the timing made sense, what it says about ownership and the front office, and how Bregman’s arrival reshapes the roster—most notably pushing Matt Shaw into a super-utility role that could benefit both the lineup and Shaw’s long-term development.

They also react to the other major news of the week: Kyle Tucker officially signing with the Dodgers. Once viewed as a potential long-term cornerstone after an MVP-caliber first half, Tucker’s Cubs tenure unraveled amid injuries, inconsistency, and a quiet finish. Brett and Michael reflect on how quickly the narrative shifted, why an extension never materialized, and what his departure means now that the Cubs have pivoted aggressively toward winning in the immediate future.

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Brett and Michael are back for the forty-fourth episode of the Bleacher Nation Cubs Podcast (Presented by Ankin Law), returning after a brief holiday break. While the Cubs were mostly quiet during that stretch, the calm didn’t last long.

Right before recording, the Cubs finally made their long-anticipated move for a controllable starting pitcher, acquiring Edward Cabrera from the Marlins in a deal first reported by Bleacher Nation’s own Michael Cerami. The trade sends top prospect Owen Caissie to Miami, along with Cristian Hernández and Edgardo De Leon, as the Cubs land a high-upside arm for the front of the rotation.

The guys break down what Cabrera brings to the table, the obvious upside, and the real risks tied to health and performance. They also discuss how this move reshapes the roster—particularly in the outfield—and whether it could reopen the door to free agency, including the possibility of a Cody Bellinger reunion.

It’s a wide-ranging conversation about timing, roster construction, and what this trade signals about how aggressively the Cubs plan to move from here.

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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.

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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.

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Brett and Michael are back for the fortieth episode of the Bleacher Nation Cubs Podcast (Presented by Ankin Law)! With the offseason still in its early stages, the guys aren’t expecting a major wave of moves just yet—but the Cubs did make their first signing of the winter, adding veteran reliever Phil Maton on a two-year, $14.5 million deal with a 2028 club option and annual incentives.

They discuss what Maton brings to the bullpen, how the deal is structured, and why he could be the first of several relief additions this offseason. Plus, more Cubs offseason talk and where things could go from here.

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Brett and Michael are back for the thirty-ninth episode of the Bleacher Nation Cubs Podcast (Presented by Ankin Law)! It’s a busy week for roster logistics, with the 40-man roster deadline and the Qualifying Offer acceptance deadline both hitting. The guys walk through how the Rule 5 Draft works and what those roster decisions mean for the Cubs heading into the winter.

They also react to Shota Imanaga accepting the Cubs’ $22 million Qualifying Offer, keeping him in Chicago for 2026. It’s a strong short-term outcome for both sides and a reflection of how much the Cubs valued bringing him back on a one-year deal.

Finally, Brett and Michael look ahead at potential offseason priorities—including whether the Cubs could make a move to solidify third base before spring training.

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