Off The Ivy: A Chicago Cubs Podcast

The Milwaukee Brewers are champions after taking down the Tampa Bay Rays in five games. While Milwaukee celebrates a championship, the Chicago Cubs are left watching their division rivals reach the top of baseball. The gap between these two organizations feels bigger than ever, and it's time to ask some serious questions about the direction of the Cubs.

TIMESTAMPS

0:00 Brewers win World Series

21:37 The difference between Pat Murphy and Craig Counsell

27:50 Seiya Suzuki qualifying offer, Sonny Gray, Cubs catchers

36:48 Cubs offseason ahead and the risk factor

The Cubs haven't finished ahead of the Brewers in the NL Central since the 2017 season ended. That's years of Milwaukee consistently finding ways to develop talent, build a winning culture, and compete at a high level while Chicago continues searching for answers.

Craig Counsell came to Chicago with a reputation as one of baseball's best managers after years of success in Milwaukee. But so far, he hasn't produced the same results with the Cubs that Pat Murphy has delivered with the Brewers. How much of that comes down to managerial decisions, and how much falls on the front office, roster construction, player development, and ownership?

In this episode, we're breaking down what separates these two organizations and what it will take for the Cubs to close the gap and other Cubs news and notes.

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With a much-anticipated MLB lockout looming, how will Jed Hoyer approach the offseason, and will the Cubs look to make their biggest moves before a potential work stoppage?

TIMESTAMPS

0:00 Brewers one win away from first World Series

18:50 Jed Hoyer's offseason approach

33:50 Tommy Hottovy and John Mallee return to coaching staff

47:20 John Schriffen officially out as White sox broadcaster

The Cubs have navigated this situation before. In 2021, Chicago signed Marcus Stroman before the lockout began, then made a major splash by signing Seiya Suzuki in the spring after the lockout ended. Could we see a similar strategy this time around? Will Hoyer be aggressive early, or will Cubs fans have to wait for the market to reopen?

We also discuss the Cubs' decision to retain Tommy Hottovy and John Mallee on the coaching staff and what that means.

And with the World Series near it's end, we have to ask: How must Craig Counsell be feeling watching the Brewers compete for the championship? What can the Cubs learn from watching baseball's biggest stage, and how close are they to building a team capable of getting there themselves?

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The Chicago Cubs’ reported pursuit of left-handed pitcher Reid Detmers was real and we’re breaking down the fallout from the deal that reportedly never happened after new information has emerged online. We dive into why the trade reportedly fell apart, with pitching prospect Jaxon Wiggins’ medicals emerging as the main reason the deal didn’t get across the finish line.

0:00 World Series Preview

7:28 Why the Reid Detmers trade to the Cubs didn't happen

18:50 Breakdown of Michael Busch's struggles in 2026

33:24 Why Cubs should sign Japanese pitcher Kaima Taira

We’re also taking a closer look at Michael Busch’s disappointing 2026 season. After high expectations, what went wrong for the Cubs first baseman? We break down the potential reasons behind his struggles and discuss what Busch needs to improve heading into 2027 to bounce back and become a more consistent force in Chicago’s lineup.

Finally, we discuss why the Cubs should be in on Japanese pitcher Kaima Taira. Could he be an intriguing option to strengthen the pitching staff? We explore why Chicago should consider pursuing him and what adding another arm could mean for the Cubs’ rotation and overall pitching depth.

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The World Series matchup is officially set, and it’s a perfect opportunity to examine what the Tampa Bay Rays and Milwaukee Brewers have done to build successful organizations without relying on the biggest payrolls in baseball. We break down why this series matters beyond the championship, focusing on how both teams excel at scouting, developing talent, and building sustainable contenders. What can the Chicago Cubs take from the way these organizations operate?

TIMESTAMPS

0:00 Brewers and Rays advance to World Series

5:00 MLB's latest CBA proposal

16:09 Freddy Peralta's impressive stint with Rays continues

21:14 Cubs poach Steve Miller from Rays to lead International Scouting Dept

25:21 Teruaki Sato could be an option for Cubs

31:10 Dansby Swanson's contract value

Speaking of the Rays, we also discuss the Cubs hiring Steve Miller to oversee the International Scouting Department with hopes to improve their international free agency (IFA) efforts and why this is such an important move for the organization’s future. With international scouting and player development playing a massive role in building a championship-caliber roster, can the Cubs improve their ability to identify and sign the next generation of impact talent?

Plus, we look at two potential Japanese players the Cubs could target and discuss how they might fit into the organization’s plans this offseason.

Later in the show, we revisit the 2022 offseason and evaluate the value Dansby Swanson has brought to the Cubs compared to Trea Turner, Xander Bogaerts, and Carlos Correa. All four were available as free agents that winter, but how does Swanson’s production, defense, and overall impact stack up against the other star shortstops? Did the Cubs make the right decision?

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The Chicago Cubs have some important questions to answer this offseason, and one of the biggest is how to get this roster younger, more athletic, and better positioned for the future. We break down the Cubs' roster construction and take a closer look at where the players who contributed this season came from.

0:00 Brewers go up 3-0 on the Dodgers in NLCS

15:03 Cubs roster breakdown in how players were acquired

30:31 Cubs catchers and how they implement Owen Ayers in 2027

38:26 Freddy Peralta's free agency & the salary cap MLB desperately wants

How many players were drafted and developed by the Cubs organization? How many were acquired through free agency? And how many came to Chicago through international free agency or trades? We examine the breakdown and what it reveals about the Cubs' ability to develop talent, build from within, and supplement the roster with outside acquisitions. What needs to change for the Cubs to build a younger, more sustainable contender?

Later in the podcast, we dive into the latest article from ESPN's Jeff Passan about MLB owners' unwavering push for a salary cap, regardless of who wins the World Series. With small-market teams making noise in October, why are owners still determined to implement a cap-and-floor system? We discuss what this fight means for the future of baseball, the players, and the possibility of a labor stoppage.

Plus, what should Cubs fans expect from the front office this offseason? Join the conversation as we examine the Cubs' future and the growing battle over the economics of Major League Baseball.

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Should Cubs fans be rooting for the Milwaukee Brewers to stick it to MLB owners?

TIMESTAMPS

0:00 MLB postseason reaction and recap

12:34 Josiah Hartshorn's future with the Cubs

21:40 Could Michael Busch play left field?

30:30 MLB notes

38:30 Better future. Cubs or White Sox?

Cody Delmendo, Dan Bernstein, and Matt Abattacola break down the massive payroll gap between the Los Angeles Dodgers and teams like the Brewers, Cleveland Guardians, and Tampa Bay Rays. What does the difference in spending say about baseball’s competitive balance, and should Cubs fans be pulling for Milwaukee to prove MLB doesn't need a salary cap.

Later in the show, we turn our attention to the Cubs’ future and discuss Josiah Hartshorn’s potential impact in 2027. Could he become an important piece of the organization’s plans? Plus, we ask an intriguing roster question: Could Michael Busch make the move to left field? We examine what that possibility could mean for the Cubs’ lineup and offseason decisions.

To close things out, we look at the future of baseball on the South Side and the North Side of Chicago. Who has the brighter future: the Chicago Cubs or the Chicago White Sox? We debate the direction of both organizations, their young talent, and which team is better positioned to compete in the years ahead.

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The MLB postseason delivered another wild day of October baseball, with the Rays, Dodgers and Brewers all punching their tickets to the League Championship Series while the Guardians stayed alive against the White Sox. We recap all of Wednesday’s playoff action and look at the biggest storylines from around the league.

TIMESTAMPS

0:00 MLB Postseason Recap

26:00 MLB getting petty already before the lockout

37:00 Cody's Top 5 Cubs in 2026

41:40 Cubs Assistant GM candidate for Athletics executive role

We also dive into MLB’s reported plans for a potential lockout, including the league removing player images and videos from its websites once the work stoppage begins. Why would MLB choose to essentially erase the players who are the face of the sport? We discuss why that decision could be another terrible look for the league as labor negotiations heat up.

Plus, Cody reveals his Top 5 individual Chicago Cubs players of the 2026 season — who made the list, who just missed it, and which performances stood out the most.

And we discuss Cubs Assistant GM Jared Banner emerging as a candidate for the Athletics' vacant top baseball executive position. What would Banner potentially leaving mean for the Cubs organization, and what does his candidacy say about the work he's done in Chicago?

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Jed Hoyer’s season-ending press conference made one thing crystal clear: the Chicago Cubs know their biggest problem is pitching.

After a disappointing Wild Card sweep by the Padres, Hoyer admitted the Cubs’ pitching struggled from the beginning of the season and acknowledged that injuries, poor performances and poor acquisitions all played a role. He also pointed directly at the Brewers’ pitching infrastructure, saying the Cubs need to “double down” in that area.

Hoyer also took responsibility for the bullpen, saying, “I did a poor job in the bullpen this year — full stop.” He emphasized that the Cubs need to improve not just the pitching staff, but the entire pitching infrastructure — from scouting and player development to major-league acquisitions.

So what does that mean for the offseason?

With multiple pitchers potentially hitting free agency and major questions surrounding the rotation and bullpen, how aggressive should the Cubs be? Do they need to make major additions through free agency and trades? And can they finally build a pitching infrastructure capable of matching the strength of their position-player group?

We break down Jed Hoyer’s comments, what they mean for the Cubs’ offseason strategy, and what needs to change if Chicago wants to take the next step in 2027.

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The Chicago Cubs’ 2026 season is over — and now the focus shifts to one of the most important offseasons of the Jed Hoyer era.

TIMESTAMPS

0:00 Cubs free agents & pitching staff headed into 2027

17:20 Cubs need a lighter clubhouse personality wise

24:53 Breaking down Ian Happ and Seiya Suzuki situations

41:35 Offseason plans for Off The Ivy

How will the Cubs attack the offseason after getting swept by the Padres? The biggest question may be what they do to rebuild a pitching staff that struggled throughout the season. The Cubs have several pitchers who will hit free agency, including Shota Imanaga, Kevin Gausman, Matthew Boyd and Clay Holmes, creating major questions for both the starting rotation and bullpen.

Then there are two massive decisions on the position-player side: Should the Cubs bring back Seiya Suzuki? Should they re-sign Ian Happ? Both are coming off the books, and the organization has to decide how much of its future payroll should be committed to its veteran outfielders.

We'll break down the Cubs' biggest offseason needs, the free agents who pitched for Chicago in 2026, the state of the rotation and bullpen, and whether Suzuki and Happ should remain part of the next version of this team.

After an 89-win season and a disappointing Wild Card exit, what should be the Cubs' biggest priority this winter?

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The Chicago Cubs’ season is over after getting swept by the San Diego Padres in the NL Wild Card Series — and the biggest problem was an offense that completely disappeared when it mattered most.

After leading MLB in runs during the regular season, the Cubs scored just one run across two playoff games and hit only .129 as a team (8-for-62). Pete Crow Armstrong and Alex Bregman went a combined 0-for-15, while the Cubs struggled to come through in key situations throughout the series.

So what happened? Why couldn’t this lineup translate its regular-season success into October? And more importantly, why couldn’t the Cubs execute better situationally at the plate when they needed a big hit, productive out, or simply a quality at-bat?

We’ll also break down the pitching decisions, including the biggest question surrounding Clay Holmes: Why didn’t the Cubs use him in the Wild Card Series? With the season on the line, was there ever a situation where Holmes should have been deployed?

Cody, Matt and Dan react to the Cubs’ disappointing two-game exit, what went wrong against San Diego, and what this loss means for the Cubs moving forward.

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See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.