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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✅ Jason Goff Unscripted

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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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The Chicago Cubs got embarrassed by the San Diego Padres to open their postseason run, and now their season is on the brink.

Matthew Boyd was tagged for THREE home runs as the Padres jumped all over the Cubs, while Chicago’s offense went completely silent for half the game — getting NO-HIT for six innings and struggling to generate any kind of momentum.

After limping into October, the Cubs now find themselves facing a must-win situation tonight. Can the offense finally wake up? Can the pitching keep the Padres in check? And can Chicago bounce back to force a decisive Game 3?

We break down the Game 1 disaster, Matthew Boyd’s outing, the Cubs’ offensive struggles and what has to change tonight to keep their season alive.

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The Chicago Cubs are back in the postseason — and it’s a rematch with the San Diego Padres, this time at Petco Park. After an 89-win regular season, the Cubs open the NL Wild Card Series tonight looking to advance and get another shot at Milwaukee.

Matthew Boyd gets the ball for Chicago in Game 1 against Padres right-hander Michael King. Boyd returns to the postseason mound against San Diego after starting Game 1 of last year’s Wild Card Series and holding the Padres to one run over 4⅓ innings. King brings a 3.21 ERA into the opener after a strong 2026 season.

But one of the biggest questions surrounding the Cubs lineup is Alex Bregman. After returning from multiple facial fractures and finishing the regular season with a huge game as the DH, will Bregman be ready to take the field at third base tonight — or will the Cubs keep him at DH? Bregman has been taking ground balls, but Craig Counsell had not made a final decision on his defensive availability.

We break down Boyd vs. King, what the Cubs need to do to win Game 1 on the road, the challenge of playing a talented Padres team in a hostile Petco Park, and how Bregman’s role could impact the lineup.

Can the Cubs steal Game 1 in San Diego and take control of the Wild Card Series?

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The Chicago Cubs are headed back to the postseason after an 89-win regular season — but they certainly aren't entering October at full strength.

Pete Crow Armstrong and Alex Bregman have been two of the biggest reasons the Cubs got here, with PCA putting together a historic season that included becoming just the seventh player in MLB history to record a 40/40 season and setting multiple Cubs offensive records along the way.

Bregman was just as important, especially in the second half. His production alongside PCA helped carry the Cubs through the final months of the season and gave Chicago a dangerous one-two punch heading into October.

But now comes the biggest question: Are the Cubs limping into the postseason? Pitching uncertainty has Chicago heading into October with plenty of questions — even after winning 89 games and clinching a playoff spot.

We'll break down PCA's incredible season, Bregman's second-half surge, what the Cubs need to clean up before the Wild Card Series and whether this team has enough left in the tank for another deep postseason run.

And we'll also take a moment to reflect on an emotional weekend around Major League Baseball, as Justin Verlander made the final start of his legendary 21-year career and Max Scherzer took the mound in what could potentially be the final start of his career.

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Pete Crow-Armstrong has officially joined baseball’s 40/40 club!

PCA stole his 40th base of the season Thursday against the Marlins, giving him 45 home runs and 40 stolen bases and making him just the seventh player in MLB history to reach the 40/40 mark. With the stolen base, he became the first to ever achieve 40 homers, 40 stolen bases, and accumulate 10.0 or more WAR in the same season, making this single season one of the greatest ever not only by a Chicago Cub but in MLB history.

And the celebration didn’t stop there. The Cubs beat Miami 2-1 to clinch their second straight postseason berth, officially punching their ticket to October. Now, with the playoff spot secured, the focus shifts to seeding.

The Cubs enter the final weekend of the regular season battling for position in the NL Wild Card race. How important will these final games be? Can Chicago secure the top Wild Card spot and home-field advantage in the Wild Card Series, or could the seeding race come down to the final day?

We break down PCA’s historic 40/40 season, potentially Ian Happ's last game at Wrigley Field, and the Cubs finally clinching their playoff spot, and everything that’s at stake this weekend as Chicago prepares for October.

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The Chicago Cubs are ONE win away from clinching a postseason berth — but the offense has gone quiet at the worst possible time.

The Cubs dropped the series to the Miami Marlins after a 3-2 loss Wednesday night, getting just two runs on Dansby Swanson’s two-run single before Miami retired the final nine Chicago hitters. The Cubs now sit at 87-71 and have seen San Diego move into the top NL Wild Card spot at 88-70, putting the Padres one game ahead of Chicago and Philadelphia.

The good news? The Cubs' magic number to clinch a postseason berth remains ONE. A win in Thursday’s home finale or an Arizona loss would send Chicago back to the playoffs.

But with the postseason approaching, the bigger question is whether this offense can get back on track. After struggling to consistently deliver in key spots against Miami, the Cubs now have to find their offense again while also trying to secure the top Wild Card position.

Are the Cubs simply going through a late-season offensive lull, or is this becoming a bigger concern heading into October?

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The Chicago Cubs had every opportunity to beat the Miami Marlins — and couldn’t cash in.

The Cubs went just 1-for-18 with runners in scoring position and left 15 runners on base in a frustrating 12-inning loss to the Marlins. But perhaps the biggest missed opportunity came in the 10th inning, when Matt Shaw couldn’t get a bunt down to move the runner and keep the Cubs’ rally alive.

In a game that stretched into extra innings, the Cubs’ inability to execute with runners on base ultimately came back to haunt them. We break down the offensive struggles, the 10th-inning rally that got away, Shaw’s bunt attempt, and what this loss says about the Cubs as they continue their push toward the postseason.

Was this simply an off night for the offense, or are the Cubs’ situational hitting problems a bigger concern? The guys also discuss a great night for the Cubs pitching staff and a the WILD development for Alex Bregman's face injury.

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Dan Bernstein, Matt Abbatacola and Cody Delmendo break down the latest on Alex Bregman after the Cubs third baseman suffered multiple facial fractures when he was struck by a foul ball in the on-deck circle. For now, it's a waiting game as doctors monitor the swelling and evaluate his recovery timeline, though the Cubs remain hopeful he'll return before the season ends. With October approaching, losing a player of Bregman's caliber would create a massive challenge for a Cubs club with postseason aspirations.

Plus, Jeff Passan's postseason award selections are out, and they include both Pete Crow-Armstrong and Bregman. Are the national accolades catching up to what Cubs fans have watched all season? The guys also revisit Daniel Palencia's recent performance and ask the big question: is he back?

Later, they dive into three critical National League matchups with Wild Card implications and what those results could mean for the playoff picture. Then they turn their attention to Wrigley Field, where the Cubs open a series against Miami with Kevin Gausman taking the mound as Chicago looks to strengthen its postseason position.

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Alex Bregman's scary face injury put a damper on an otherwise successful weekend for the Chicago Cubs, who secured their third straight series victory and moved their magic number to clinch a postseason spot down to just one after taking two out of three in Cincinnati.

In this episode, we break down Bregman's injury, the impact it could have on the Cubs heading into October, an update on PCA's historic season, and the team's continued push toward the playoffs. With the postseason within reach, how concerned should Cubs fans be about Bregman's health?

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The Chicago Cubs enjoyed their off day at Churchill Downs, where PCA and his teammates watched Alex Bregman's horse pick up a big win! But that victory takes on an even more interesting meaning when you look back at Cubs history.

As PCA continues his historic season, chasing Rogers Hornsby for the all-time single-season Cubs WAR record. Hornsby was not only one of the greatest players in franchise history, but also had a well-documented gambling addiction, particularly when it came to horse racing.

We'll break down PCA's pursuit of Hornsby, the connection between Bregman's horse and one of the most fascinating figures in Cubs history, and what this historic chase means as the regular season winds down.

Dan, Matt, and Cody also discuss Seiya Suzuki's season and what's looming at the end of the season when he becomes a free agent.

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✅ Dan Bernstein Unfiltered

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✅ Jason Goff Unscripted

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Pete Crow Armstrong's historic 2026 season just reached another milestone! The Cubs star launched two more home runs against the Atlanta Braves last night, cementing his place in franchise history.

PCA is now the Chicago Cubs' all-time leader in home runs in a single season by a left-handed hitter, surpassing hall of famer Billy Williams in 1970. Even more impressive? He's now tied with Ernie Banks for the most home runs in a single season by a player at his age in Cubs history.

From his power surge to his impact on both sides of the ball, PCA continues to make history as the Cubs push toward October baseball.

With a big night from PCA and Alex Bregman, Shota Imanaga also delivered another fantastic outing to continue a great September run. Can the Cubs trust him in October? Matt, Dan, and Cody discuss it all in this episode.

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The Best Replacement Windows And Doors At The Best Price. Chicagowindowguys.com

Give Larine a try. Right now, Larineco is offering our listeners up to 50% off at buylarine.com/ivy

Make sure to subscribe to...

✅ Dan Bernstein Unfiltered

✅ Forward Progress - A Chicago Bears Podcast 🏈

✅ Organization Win Championships: A Chicago Bulls Podcast 🏀

✅ Jason Goff Unscripted

All links to YouTube, Apple, Spotify and more available on 312Sports.com

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