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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Brett and Michael are back for the thirty-eighth episode of the Bleacher Nation Cubs Podcast (Presented by Ankin Law)! Not much movement yet in the Cubs’ offseason, but the big storyline remains Shota Imanaga’s qualifying offer decision, which must come by November 18.

Reports suggest Imanaga is expected to decline the $22 million offer, with his camp exploring what his market might look like if he does. If he accepts, he’ll return to the Cubs for 2026. If he declines, he could still re-sign in Chicago—but if he signs elsewhere, the Cubs would receive a compensatory draft pick after the second round.

Meanwhile, all signs point to the Cubs being active in the starting pitching market, with names like Tatsuya Imai, Dylan Cease, and others emerging as possible targets. The guys dig into Cease’s current career arc and discuss what kind of deal or trade value he might carry.

Finally, they ask the offseason question on everyone’s mind: could the Cubs bring back Cody Bellinger?

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Brett and Michael are back for the thirty-seventh episode of the Bleacher Nation Cubs Podcast (Presented by Ankin Law)! They discuss the Cubs’ decision to decline Shota Imanaga’s option, what it means for his future, and whether a Qualifying Offer could still be in play. 

They also touch on Shane Bieber’s surprising one-year deal to stay in Toronto, how front offices are approaching short-term pitching contracts, and the Cubs’ new one-year agreement with Colin Rea heading into 2026.

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Brett and Michael are back for the thirty-sixth episode of the Bleacher Nation Cubs Podcast (Presented by Ankin Law)! With the baseball season nearing its end, the guys talk through a range of topics—from dominant postseason pitching performances to what lies ahead for the Cubs.

They start by discussing Trey Yesavage’s breakout playoff and World Series run, and where a pitcher with his stuff would have finished the year if he were a Cubs prospect—Double-A? Triple-A? The conversation expands into the growing league-wide trend toward promoting talented young pitchers earlier. With more arms entering pro ball already polished, are teams ready to embrace a true youth movement on the mound? And could future CBA changes accelerate that timeline even more?

The guys also dive into Jon Heyman’s report about the Cubs’ unwillingness to structure a Shohei Ohtani contract the same way the Dodgers did—with 97% of his record $700 million deferred. They unpack how that shaped the final bidding process, what the Cubs’ reported $500 million offer says about their strategy, and whether the Dodgers’ deferral-heavy model offered hidden tax benefits that helped seal the deal.

Finally, they reflect on where the Cubs stand in relation to true World Series contenders—what’s in place, what’s missing, and how far they really are from being the next team to make a deep October run.

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Brett and Michael are back for the thirty-fifth episode of the Bleacher Nation Cubs Podcast (Presented by Ankin Law)! It’s that tricky part of the offseason where storylines are just starting to form, but there’s still plenty to dig into.

The guys discuss the Dodgers’ rumored interest in Kyler Tucker, and how it fits the trend of big-name players being tied to big Cubs offseasons—though major fireworks haven’t arrived just yet. They also look at the current roster structure and how few obvious openings the Cubs actually have.

Starting pitching remains an area of need, and the conversation turns to how the Cubs might approach it. Some of the arms discussed back in July could resurface as trade or short-term free-agent targets, as none of those pitchers ended up being moved at the deadline. While the team would likely prefer shorter deals, there’s also recognition that cost-controlled options could be appealing through trade. That said, it’s tough to imagine another big December splash just a year after the last one.

They also take a longer view, discussing Dansby Swanson’s performance three years into his seven-year, $177 million deal and what that contract looks like now that the first half of his tenure is in the books.

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Brett and Michael are back for the thirty-fourth episode of the Bleacher Nation Cubs Podcast (Presented by Ankin Law)—the first episode of the offseason. They reflect on what was a memorable 2025 campaign, one that ended just two runs short of the NLCS after falling 3–1 to the Brewers in Game 5 of the NLDS.

The guys talk through the sense of closure following the season, the excitement of five postseason games at Wrigley Field, and the legacy this team leaves behind. It was a year defined by progress, competitiveness, and the kind of energy fans have been waiting for.

They also look back on individual storylines—especially Kyle Tucker’s season, which started at a superstar level before injuries and inconsistency took the shine off his overall numbers. Even though his production wasn’t disastrous, the narrative of his season ended up being dominated by injuries, slumps, and a late-summer benching in Milwaukee.

In contrast, they highlight the steady impact of players like Carson Kelly, whose reliability and clutch performances became defining moments down the stretch.

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