Explore every episode of the podcast Off The Ivy: A Chicago Cubs Podcast

The Chicago Cubs are being linked to two-time Cy Young Award winner Tarik Skubal, and this might be the biggest opportunity for the franchise to make a statement this offseason. But are the Cubs willing to spend what it takes to land one of the best pitchers in baseball?

TIMESTAMPS

0:00 Cubs reportedly want Tarik Skubal badly

16:20 Cubs pitchers entering free agency

22:55 Jason Kanzler takes Mariners Managerial job

34:30 Seiya Suzuki linked to Toronto

With the 2026 season behind us, the Cubs have some major questions to answer about their starting rotation. Several key starters are entering free agency, and the uncertainty surrounding the health and consistency of the remaining rotation makes adding an established ace an absolute priority.

Why shouldn't the Cubs go all-in on Tarik Skubal? We'll break down the Cubs' biggest pitching needs, why Skubal could transform this rotation into a legitimate World Series contender, and what Chicago's payroll looks like entering the 2026-27 offseason. With less than $200 million in projected 2027 payroll commitments, does Jed Hoyer have the financial flexibility to make a historic offer?

And that's not all!

⚾ ALSO IN TODAY'S SHOW:

• Jason Kanzler to Seattle: The former Cubs Director of Player Development has officially been named the new manager of the Seattle Mariners. What does his departure mean for the Cubs organization, and what can Mariners fans expect?
• Seiya Suzuki to Toronto? The Blue Jays are reportedly expected to be in the mix for Suzuki in free agency. Could the Cubs lose one of their biggest offensive weapons to a potential AL contender?

The Cubs have some huge decisions ahead. Is it finally time for the Ricketts family to open the checkbook and bring an elite ace to the North Side?

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✅ Dan Bernstein Unfiltered

✅ Forward Progress - A Chicago Bears Podcast 🏈

✅ Organization Win Championships: A Chicago Bulls Podcast 🏀

✅ Jason Goff Unscripted

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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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✅ Dan Bernstein Unfiltered

✅ Forward Progress - A Chicago Bears Podcast 🏈

✅ Organization Win Championships: A Chicago Bulls Podcast 🏀

✅ Jason Goff Unscripted

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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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✅ Dan Bernstein Unfiltered

✅ Forward Progress - A Chicago Bears Podcast 🏈

✅ Organization Win Championships: A Chicago Bulls Podcast 🏀

✅ Jason Goff Unscripted

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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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✅ Dan Bernstein Unfiltered

✅ Forward Progress - A Chicago Bears Podcast 🏈

✅ Organization Win Championships: A Chicago Bulls Podcast 🏀

✅ Jason Goff Unscripted

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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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✅ Dan Bernstein Unfiltered

✅ Forward Progress - A Chicago Bears Podcast 🏈

✅ Organization Win Championships: A Chicago Bulls Podcast 🏀

✅ 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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✅ Dan Bernstein Unfiltered

✅ Forward Progress - A Chicago Bears Podcast 🏈

✅ Organization Win Championships: A Chicago Bulls Podcast 🏀

✅ Jason Goff Unscripted

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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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✅ Dan Bernstein Unfiltered

✅ Forward Progress - A Chicago Bears Podcast 🏈

✅ Organization Win Championships: A Chicago Bulls Podcast 🏀

✅ Jason Goff Unscripted

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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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✅ Dan Bernstein Unfiltered

✅ Forward Progress - A Chicago Bears Podcast 🏈

✅ Organization Win Championships: A Chicago Bulls Podcast 🏀

✅ Jason Goff Unscripted

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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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✅ Dan Bernstein Unfiltered

✅ Forward Progress - A Chicago Bears Podcast 🏈

✅ Organization Win Championships: A Chicago Bulls Podcast 🏀

✅ Jason Goff Unscripted

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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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✅ Dan Bernstein Unfiltered

✅ Forward Progress - A Chicago Bears Podcast 🏈

✅ Organization Win Championships: A Chicago Bulls Podcast 🏀

✅ Jason Goff Unscripted

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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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✅ Dan Bernstein Unfiltered

✅ Forward Progress - A Chicago Bears Podcast 🏈

✅ Organization Win Championships: A Chicago Bulls Podcast 🏀

✅ Jason Goff Unscripted

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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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✅ Dan Bernstein Unfiltered

✅ Forward Progress - A Chicago Bears Podcast 🏈

✅ Organization Win Championships: A Chicago Bulls Podcast 🏀

✅ Jason Goff Unscripted

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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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✅ Dan Bernstein Unfiltered

✅ Forward Progress - A Chicago Bears Podcast 🏈

✅ Organization Win Championships: A Chicago Bulls Podcast 🏀

✅ Jason Goff Unscripted

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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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✅ Dan Bernstein Unfiltered

✅ Forward Progress - A Chicago Bears Podcast 🏈

✅ Organization Win Championships: A Chicago Bulls Podcast 🏀

✅ Jason Goff Unscripted

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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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✅ Dan Bernstein Unfiltered

✅ Forward Progress - A Chicago Bears Podcast 🏈

✅ Organization Win Championships: A Chicago Bulls Podcast 🏀

✅ Jason Goff Unscripted

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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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✅ Dan Bernstein Unfiltered

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✅ Organization Win Championships: A Chicago Bulls Podcast 🏀

✅ Jason Goff Unscripted

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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 Unfiltered

✅ Forward Progress - A Chicago Bears Podcast 🏈

✅ Organization Win Championships: A Chicago Bulls Podcast 🏀

✅ Jason Goff Unscripted

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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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✅ Dan Bernstein Unfiltered

✅ Forward Progress - A Chicago Bears Podcast 🏈

✅ Organization Win Championships: A Chicago Bulls Podcast 🏀

✅ Jason Goff Unscripted

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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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✅ Dan Bernstein Unfiltered

✅ Forward Progress - A Chicago Bears Podcast 🏈

✅ Organization Win Championships: A Chicago Bulls Podcast 🏀

✅ Jason Goff Unscripted

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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

✅ Forward Progress - A Chicago Bears Podcast 🏈

✅ Organization Win Championships: A Chicago Bulls Podcast 🏀

✅ 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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✅ Dan Bernstein Unfiltered

✅ Forward Progress - A Chicago Bears Podcast 🏈

✅ Organization Win Championships: A Chicago Bulls Podcast 🏀

✅ Jason Goff Unscripted

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The Chicago Cubs' bullpen imploded yet again in September, blowing a 3-0 lead in Tuesday night's 6-3 loss to the Atlanta Braves. With the postseason approaching, the Cubs' pitching issues continue to raise serious concerns. Jacob Webb surrendered the go-ahead home run to Ozzie Albies, while Edward Cabrera gave up another long ball in the ninth inning to Drake Baldwin to put the game out of reach.

Cody, Matt, and Dan break down another frustrating night for the Cubs' bullpen, examine Webb's struggles in high-leverage situations, and discuss what Edward Cabrera's outing means for Chicago's pitching staff moving forward. Can the Cubs fix these issues before October, or will their bullpen ultimately cost them in the playoffs?

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✅ Dan Bernstein Unfiltered

✅ Forward Progress - A Chicago Bears Podcast 🏈

✅ Organization Win Championships: A Chicago Bulls Podcast 🏀

✅ Jason Goff Unscripted

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Pete Crow-Armstrong is making Cubs history — and he’s getting closer to an incredible 40/40 season! 🔥

PCA launched his 42nd home run of the season, tying Cubs legend Billy Williams for the most home runs ever by a left-handed hitter in franchise history. But he wasn’t done there. Crow-Armstrong also stole a base, he reached 100 runs batted in and continued to push himself toward the rare 40-home run, 40-steal milestone.

And perhaps most importantly, the Cubs took care of business against the Braves, picking up another huge win as they inch closer to clinching a playoff spot.

In this episode, we break down PCA’s historic season, his pursuit of 40/40, what this record-tying homer means in Cubs history, and how important this win over Atlanta is with October getting closer.

Is PCA putting together the greatest season by a Cubs left-handed hitter ever? And just how close are the Cubs to officially punching their ticket to the postseason?

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✅ Dan Bernstein Unfiltered

✅ Forward Progress - A Chicago Bears Podcast 🏈

✅ Organization Win Championships: A Chicago Bulls Podcast 🏀

✅ Jason Goff Unscripted

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The Chicago Cubs needed a response after getting swept by the Brewers — and they got one this weekend against the Pittsburgh Pirates.

Alex Bregman stepped up in a big way, helping lead the Cubs back in the right direction while the offense showed signs of life. We discuss how he's been the second most valuable player in MLB since the All-Star Break and his season shift overall. But perhaps the biggest development was the Cubs bullpen, which took some significant steps forward after struggling mightily in recent weeks.

Can Bregman continue to be a difference-maker down the stretch? And has the Cubs bullpen finally started to turn things around at the most important time of the season?

With the NL Wild Card race tight, every game matters. We break down the Cubs' bounce-back weekend, Bregman's impact, the bullpen's improvement and what it could mean for the final push toward October.

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✅ Dan Bernstein Unfiltered

✅ Forward Progress - A Chicago Bears Podcast 🏈

✅ Organization Win Championships: A Chicago Bulls Podcast 🏀

✅ Jason Goff Unscripted

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The Chicago Cubs are off to a 3-6 start in September, and with October getting closer, the margin for error is shrinking fast.

In this episode, we break down the Cubs’ latest playoff odds and what this rough stretch means for their chances of making the postseason. Are the Cubs putting themselves in danger of falling out of the playoff picture, or is there still enough time to turn things around?

We’ll also look ahead at the remaining schedule and ask an important question: What matchups should the Cubs actually prefer in the postseason between the Phillies or the Braves? Which teams give Chicago the best opportunity to gain ground, and which opponents could make the road to October even tougher?

With the NL Wild Card race tightening, every series matters. We’ll break down where the Cubs stand, what they need to do, and whether they can get back on track before it’s too late.

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✅ Dan Bernstein Unfiltered

✅ Forward Progress - A Chicago Bears Podcast 🏈

✅ Organization Win Championships: A Chicago Bulls Podcast 🏀

✅ Jason Goff Unscripted

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The Chicago Cubs have been SWEPT by the Milwaukee Brewers, and this series exposed a major difference between these two teams: pitching infrastructure.

The Brewers continue to develop, identify, and build pitching at a level the Cubs simply haven't been able to match. From their rotation depth to their bullpen and the way they consistently find arms to get big outs, Milwaukee’s pitching infrastructure looks YEARS ahead of Chicago’s.

And with the Cubs struggling to get reliable innings and late-game outs, the question now has to be asked: ARE THE CUBS IN TROUBLE OF MISSING THE PLAYOFFS?

The NL Wild Card race is getting tighter, the margin for error is shrinking, and the Brewers just reminded everyone why they're the team to beat.

Is this just a bad series for the Cubs — or is it a sign of a much bigger problem?

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✅ Dan Bernstein Unfiltered

✅ Forward Progress - A Chicago Bears Podcast 🏈

✅ Organization Win Championships: A Chicago Bulls Podcast 🏀

✅ Jason Goff Unscripted

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The Chicago Cubs blew another late lead against the Milwaukee Brewers tonight, and this one hurts even more as they drop the series in Milwaukee.

Carson Kelly came through with a huge late hit to give the Cubs the lead and put them in position to steal the game. But once again, the bullpen couldn’t hold it — and Jacob Webb ultimately became the reason the Cubs lost.

Webb’s outing turned a two-run lead with two outs in the 9th inning into another brutal loss in extra innings, raising even more questions about Craig Counsell’s bullpen decisions and whether the Cubs have enough reliable arms to survive the stretch run.

The Cubs are running out of opportunities, and these late-inning collapses against Milwaukee could come back to haunt them when the playoff picture is decided.

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✅ Dan Bernstein Unfiltered

✅ Forward Progress - A Chicago Bears Podcast 🏈

✅ Organization Win Championships: A Chicago Bulls Podcast 🏀

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The Chicago Cubs suffered another frustrating loss to the Milwaukee Brewers, and once again, the bullpen became the biggest story.

After Matthew Boyd delivered a strong outing, Craig Counsell’s decision to send Boyd back out for the 8th inning deserves some serious scrutiny. Was it the right call to push Boyd deeper into the game, or did the Cubs manager put his team in a position to give the Brewers a chance to take control?

Once again, Chicago’s bullpen couldn’t hold the line, and these late-game collapses are becoming increasingly concerning as the Cubs fight for their postseason position.

With the NL Wild Card standings becoming more important by the day, every game carries enormous weight. The Cubs simply cannot afford to keep giving away winnable games, especially with October baseball getting closer.

We’ll break down the loss, Counsell’s decision with Boyd, the bullpen’s latest meltdown, and where the Cubs currently stand in the crowded NL Wild Card race.

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✅ Dan Bernstein Unfiltered

✅ Forward Progress - A Chicago Bears Podcast 🏈

✅ Organization Win Championships: A Chicago Bulls Podcast 🏀

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Kevin Gausman and Pete Crow-Armstrong came up HUGE as the Chicago Cubs defeated the Milwaukee Brewers tonight to split the series!

Gausman delivered a dominant start when the Cubs needed it most, keeping the Brewers' offense in check and giving Chicago a chance to win. Meanwhile, PCA continued to make his impact felt at the plate and in the field, helping lead the Cubs to a crucial victory with a 2-run homer that ended up being the game winning hit.

After dropping the first two games of the series, the Cubs respond by taking the finale and leave Wrigley Field with a split. We break down Gausman's impressive outing, PCA's big night, the biggest moments from the game, and what this win means for the Cubs as they continue their push toward October.

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✅ Dan Bernstein Unfiltered

✅ Forward Progress - A Chicago Bears Podcast 🏈

✅ Organization Win Championships: A Chicago Bulls Podcast 🏀

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The Chicago Cubs have dropped their second straight game to the Milwaukee Brewers, and this one hurts even more considering the opportunity they had against Jacob Misiorowski.

Misiorowski turned in his worst start of the season, but the Cubs still couldn’t take advantage and come away with a win. Alex Bregman was the difference-maker for the Cubs offense, putting together a huge game and giving the Cubs exactly the kind of offensive performance they needed in a critical matchup but David Peterson didn't have a good performance and the Cubs bullpen struggled at certain points again.

We break down the loss, Bregman’s big night, the Cubs’ missed opportunities against the Brewers bullpen, and what dropping two straight to Milwaukee means for the Cubs as the race for October baseball heats up.

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✅ Dan Bernstein Unfiltered

✅ Forward Progress - A Chicago Bears Podcast 🏈

✅ Organization Win Championships: A Chicago Bulls Podcast 🏀

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The Chicago Cubs had a 3-0 lead over the Milwaukee Brewers — and somehow managed to let it completely slip away.

In this episode, we break down a brutal night for the Cubs bullpen and how the game unraveled after Chicago put itself in position to win. Daniel Palencia’s outing is a major focus, as the right-hander once again struggled in a critical spot and put even more pressure on a bullpen that simply could not hold the line. Palencia allowed 2 runs in just 2/3 of an inning, continuing a troubling recent stretch.

We'll look at how the Cubs blew the 3-0 advantage, the biggest mistakes from the bullpen, Craig Counsell's decisions, and what this loss could mean for Chicago as the Cubs continue their push against the Brewers and toward October.

Was this just one bad night, or is the Cubs bullpen becoming a legitimate postseason concern?

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✅ Dan Bernstein Unfiltered

✅ Forward Progress - A Chicago Bears Podcast 🏈

✅ Organization Win Championships: A Chicago Bulls Podcast 🏀

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The Chicago Cubs put on an absolute power display, launching 9 home runs to set a new franchise record en route to a dominant victory over the Milwaukee Brewers!

From the opening innings, the Cubs’ bats were locked in, delivering one big swing after another and turning the game into a historic offensive showcase. The long balls kept coming as Chicago overwhelmed Milwaukee and powered its way to a statement win.

Clay Holmes also maintained his dominate run since joining the Cubs throwing a quality start. In this episode, the guys discuss the dominating win behind Holmes, Alex Bregman's three homeruns, and Pat Murphy inserting a position player in the seventh inning to avoid using more of his bullpen.

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✅ Dan Bernstein Unfiltered

✅ Forward Progress - A Chicago Bears Podcast 🏈

✅ Organization Win Championships: A Chicago Bulls Podcast 🏀

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PCA hit five home runs this weekend, but somehow the Chicago Cubs still walked away without winning the series against the Cincinnati Reds.

We break down PCA’s incredible power surge, what made his weekend so impressive, and why the Cubs couldn’t turn his production into enough wins. With the season entering its most important stretch, Chicago needs to find a way to capitalize when its biggest stars are playing at this level.

Are the Cubs wasting a huge opportunity down the stretch? And can PCA continue his MVP caliber season with this kind of production as the Cubs push toward October?

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✅ Dan Bernstein Unfiltered

✅ Forward Progress - A Chicago Bears Podcast 🏈

✅ Organization Win Championships: A Chicago Bulls Podcast 🏀

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The Cubs are officially entering crunch time with October baseball getting closer by the day. In this episode, we break down Chicago’s latest playoff picture, where they currently stand in the NL Wild Card race, and what their remaining schedule means for their postseason chances. The Cubs are 76-58 and hold a four-game Wild Card cushion, but they’ve also dropped five of their last seven games.

We’ll take a closer look at the massive upcoming stretch against the Reds and Brewers, including a four-game series with Milwaukee that could have major implications for the NL Central and playoff seeding. With just 28 games remaining, every win and loss is becoming increasingly important.

Can the Cubs hold onto their playoff spot and make a serious push toward October? Or are the recent struggles a sign of trouble ahead?

Also, with the organization celebrating the 150th anniversary of the franchise, we decided to make the Chicago Cubs 150th Anniversary Pretty Good Team.

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✅ Dan Bernstein Unfiltered

✅ Forward Progress - A Chicago Bears Podcast 🏈

✅ Organization Win Championships: A Chicago Bulls Podcast 🏀

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The Chicago Cubs dropped the series in Arizona, and this one leaves plenty to talk about. The Cubs struggled to put together enough consistent offense and execution, but one of the biggest talking points came late when Pete Crow Armstrong got into a heated argument with the umpires over what appeared to be a pretty obvious missed balk call.

PCA wasn’t happy, and neither were Cubs fans watching the play unfold. Was the missed call as obvious as it looked? We break down the controversial moment, PCA’s reaction, and how the Cubs ultimately let another winnable game — and another series — slip away.

We’ll also look at the bigger picture for the Cubs as they try to keep pace in the NL Central and figure out how to turn these frustrating stretches around.

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✅ Dan Bernstein Unfiltered

✅ Forward Progress - A Chicago Bears Podcast 🏈

✅ Organization Win Championships: A Chicago Bulls Podcast 🏀

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The Chicago Cubs suffered a brutal bullpen collapse against the Arizona Diamondbacks, turning a four-run lead in the late innings into a frustrating loss. Daniel Palencia and Jacob Webb were at the center of the meltdown, as the Cubs’ relief pitching once again raised serious concerns.

We’ll break down what went wrong for Palencia and Webb, the costly mistakes that allowed Arizona to take control, and what this means for Craig Counsell and the Cubs moving forward. Can this bullpen be trusted when the games matter most?

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The Chicago Cubs put together a statement win in the desert, shutting out the Arizona Diamondbacks 7-0 behind an absolutely dominant start from Kevin Gausman. Gausman delivered seven scoreless innings, allowing just three hits and one walk while striking out six.

The Cubs offense gave him plenty of support, with Michael Conforto continuing his recent surge by collecting three hits, including a huge two-run homer. Ian Happ also came through with two hits and an RBI, continuing his hot stretch over the last two weeks.

After a frustrating stretch, the Cubs have now responded with back-to-back dominant victories and 26 unanswered runs over their last two games. Can Gausman's performance be the start of a major turnaround for the rotation as Chicago makes its push down the stretch?

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✅ Dan Bernstein Unfiltered

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The Chicago Cubs finally got back in the win column yesterday, with Ian Happ's grand slam and Pete Crow Armstrong's 2-run homer leading the way in a much-needed victory. But while the Cubs were able to finish the weekend on a high note, their overall play over the last few days was anything but encouraging.

Friday was especially frustrating, with the Cubs going just 1-for-16 with runners in scoring position as the offense repeatedly failed to come through in big moments. There are also growing concerns about Ryan Zeferjahn and whether the Cubs can consistently trust him in high leverage spots out of their bullpen moving forward.

Then came Saturday, when Jacob Webb had a chance to close things out in the 9th inning but instead watched the game slip away. His first runs allowed since the end of June came at the wrong time.

Ian Happ and PCA helped provide a much-needed spark yesterday, but can the Cubs actually build some momentum from here and regain some ground before Milwaukee comes to Wrigley Field next week?

We break down the win, the offensive struggles, the bullpen concerns, and everything that went wrong over the weekend for the Cubs.

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✅ Dan Bernstein Unfiltered

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The Chicago Cubs head to Seattle this weekend for a three-game series against the Mariners, looking to keep pace in a heated NL Central race. The Cubs enter the series at 74-54, sitting five games behind the first-place Milwaukee Brewers with the season entering a critical stretch.

We’ll preview the weekend matchup, look at the pitching matchups, key players to watch, and what the Cubs need to do to come away from Seattle with a series win. Seattle will also be looking to bounce back after dropping a series to Milwaukee, adding another layer of intrigue to this interleague matchup.

The biggest question: Can the Cubs continue to chip away at Milwaukee’s lead? With every game becoming more important, the Cubs can’t afford to waste opportunities as they chase the Brewers for the NL Central crown.

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The Chicago Cubs couldn’t complete the sweep, dropping the series finale to the White Sox 3-0 at Wrigley Field. Jose Urquidy dominated out of the White Sox bullpen, while the Cubs struggled to generate offense in the loss despite back-to-back great starts by Clay Holmes.

But the bigger story is the latest injury news surrounding the Cubs. Craig Counsell provided updates on Daniel Palencia, Justin Steele and Ben Brown as the Cubs navigate a critical stretch of the season with their pitching staff dealing with multiple injuries. We break down what Counsell had to say, where each pitcher stands and what these updates could mean for the Cubs moving forward.

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Alex Bregman came through when the Cubs needed him most twice last night!

For the second straight game, the Cubs walk off the White Sox, this time behind Bregman's clutch hits to help providing both the game-tying and game-winning knocks in another wild finish at Wrigley. We break down Bregman’s heroics and what his presence has meant for the Cubs lineup.

We’re also talking about Pete Crow-Armstrong, who continues to make his case as one of the most exciting young stars in baseball after launching another lead off home run in this series. We take a look at his numbers, his impact, and what it would take for him to make a legitimate run at the award.

And don’t overlook Javier Assad, who has quietly been one of the most valuable pieces on this Cubs team all season. We discuss just how important Assad has been, the ways he continues to contribute, and why his value to the Cubs goes beyond the box score.

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What a night at Wrigley! The Chicago Cubs delivered a dramatic comeback and an electric finish, capped by Pete Crow-Armstrong's walk-off hit against the White Sox.

The atmosphere was absolutely INSANE as the Cubs battled back late. Nico Hoerner came through with a clutch game-tying hit in the bottom of the 9th, setting the stage for PCA to play the hero.

Jacob Webb then slammed the door with a shutdown top of the 10th, giving the Cubs the perfect opportunity to finish the game. And none of it would have been possible without another strong outing from Shota Imanaga, who kept the Cubs in the game and gave the offense a chance to rally.

From Imanaga's performance to Hoerner's ninth-inning heroics, Webb's dominant 10th, and PCA's walk-off and full performance — this was a night Cubs fans won't forget.

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The Cubs’ weekend against the Cardinals went from promising to disastrous in a hurry.

Chicago dropped two straight games to St. Louis after winning Friday’s opener, but the biggest concern coming out of the weekend is Dansby Swanson. The Cubs’ shortstop left Sunday’s game after an awkward swing and is headed to the injured list with a left oblique injury. An MRI is expected to provide more clarity on the severity and timeline, but losing Swanson at this point of the season could be a massive blow for a deep playoff run for the Cubs.

Then there was Edward Cabrera’s nightmare return to the rotation. Cabrera gave up 7 runs on 6 hits and 3 walks in just 3.2 innings, as the Cardinals erupted for six runs in the fourth inning. To make matters worse, Cabrera revealed afterward that a blister was affecting him during the outing.

The Cardinals ultimately cruised to an 11-4 victory, taking the weekend series 2-1 and leaving the Cubs with plenty of questions heading into a crucial stretch of the season.

In this episode, we break down:

• How serious Dansby Swanson’s injury could be
• Edward Cabrera’s disastrous outing and what comes next
• Why the Cubs couldn’t close out the Cardinals
• What this series loss means for the NL Central race
• Where the Cubs go from here

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The Chicago Cubs laid an egg yesterday, but they’re still heading home with a winning road trip.

Cade Cavalli was outstanding for the Washington Nationals, shutting down the Cubs’ offense and making sure Chicago never really got anything going. It was a frustrating way to finish the trip, but the bigger picture remains positive: the Cubs return home having won the road trip and with plenty to build on with the Cardinals coming to Wrigley Field this weekend.

We’ll break down what went wrong against Cavalli, what the Cubs need to clean up, and why there’s still plenty to like about this team coming home.

Then, we’re taking a deep dive into Michael Busch’s season so far. What has stood out about his performance? Where has he improved, where does he still need to get better, and what could the rest of the season look like for Busch?

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Alex Bregman just made history!

Bregman launched three home runs in a game for the first time in his career, powering the Chicago Cubs to a dominant blowout victory over the Washington Nationals to win their 9th consecutive series on the road.

From his first blast to his third, Bregman was locked in all night as the Cubs’ offense exploded and put the game out of reach. Dansby Swanson also added his 18th homer of the season to help ignite the Cubs offense along the way. Seiya Suzuki and Pedro Ramirez added two hits. Pete Crow-Armstrong got the Cubs on the board with a rbi-double against Chicago area native Jackson Kent. The Cubs lineup has now scored double digit runs in back-to-back days and go for the sweep this afternoon.

In this episode, Dan, Matt, and Cody discuss Bregman's resurgence and where their division chances sit after Milwaukee lost again last night.

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PCA, Alex Bregman and Seiya Suzuki powered the Cubs to a big win over the Nationals last night! 💥⚾

The Cubs’ bats came alive as Pete Crow-Armstrong, Bregman and Suzuki delivered key hits and big swings to help Chicago take down Washington. Shota Imanaga had a tough start, but the Cubs bullpen locked it down late, including another big outing by Jacob Webb.

In this episode, Cody, Dan, and Matt discuss the Cubs seventh win in the club's last eight games.

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Pete Crow-Armstrong and Shohei Ohtani are making the NL MVP race VERY interesting.

PCA has emerged as the biggest threats to Shohei Ohtani’s MVP reign — and there’s a legitimate argument that he should be the front-runner right now.

The Cubs star is doing it ALL: elite offense, game-changing speed, Gold Glove-level defense, and the kind of overall impact that shows up in the advanced metrics. He’s currently sitting at the top of the league in WAR while putting together an offensive season that nobody saw coming after his struggles in the second half of 2025.

And then there’s the defense. PCA isn’t just a great hitter playing center field — he’s the best defensive center fielder in baseball, making plays that most players simply can’t get to.

In this episode, Dan, Cody, and Matt break down PCA’s MVP case, his numbers, his defense, the Ohtani comparison, and what needs to happen over the final stretch of the season for him to take home the award.

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Ian Happ is FINALLY heating up for the Chicago Cubs

After struggling at the plate since early June, Happ broke out against the Royals this weekend, collecting three hits and launching his 20th home run of the season in Sunday’s 10-2 win. Is this the start of another Happ hot streak?

Plus, Matthew Boyd continues to look like a completely different pitcher since returning from his knee injury. After missing seven weeks, Boyd has provided the Cubs with consistent, high-quality starts — including seven strong innings against Kansas City on Sunday to secure the series victory.

And then there’s Kevin Gausman. In his first start as a Cub, Gausman delivered exactly what Chicago hoped for, throwing seven innings and allowing just two runs in a 6-4 win over the Royals.

We break down Happ’s potential breakout, Boyd’s impressive comeback, and what Gausman’s debut could mean for the Cubs’ rotation as Chicago makes its push toward October.

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Pete Crow-Armstrong and Alex Bregman delivered in the biggest moments as the Cubs stormed back to stun the Toronto Blue Jays and extend their winning streak to four games. After being held in check for most of the afternoon by Cy Young candidate Dylan Cease, Bregman crushed a clutch two-out, two-run homer in the 9th inning to tie the game, and PCA sparked the 11th inning rally with a knock, stealing third base, and scoring the winning run on a throwing error to complete an unforgettable comeback.

In this episode, we break down:

Bregman's game-tying blast in the 9th

PCA's electric extra-inning heroics on the bases

The key moments that fueled the comeback

What this fourth straight win means for the Cubs moving forward

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Pete Crow-Armstrong put on a show, launching TWO home runs as the Chicago Cubs completed a statement sweep of the Los Angeles Dodgers! With another huge performance, PCA continues to strengthen his case in the National League MVP race, putting more pressure on reigning superstar Shohei Ohtani.

In this episode, we break down:

• PCA's two-homer performance and biggest moments
• How the Cubs dominated the Dodgers to complete the sweep
• Why Crow-Armstrong's MVP stock keeps rising
• How he compares to Shohei Ohtani in the NL MVP race
• What this means for the Cubs as they push toward the postseason

Is Pete Crow-Armstrong the new favorite for NL MVP, or does Shohei Ohtani still have the edge?

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