Windy City Breakdown

The Cubs bullpen -- which looked like a strength earlier in the year -- scuffled in a tough loss to the Brewers at Wrigley Field. Tony Andracki, Kyle Millinowisch and Andy Martínez break down the reliever issues for the Cubs and how concerned they are for the team as a whole with the playoffs nearing. 

The trio breaks down what's going on with the Cubs, whether they could have done more and who or what may be the answer for their bullpen woes. Later in the pod, the group discusses who will be the X-Factor down the stretch, and their concern for the team: the Philadelphia Phillies. 

The Windy City Breakdown then dives into the Bears, as the NFL season nears. They discuss what their biggest concern for the team is and who the No. 1 Bears player they're targeting in fantasy football this year.

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The Cubs suffered a pair of difficult walk-off losses to the Mariners and Diamondbacks, then received some concerning news on right-hander Ben Brown. Tony Andracki, Kyle Millinowisch and Andy Martínez discuss the state of the Cubs after their West Coast trip. The trio also discuss whether or not you should be concerned about the Cubs bullpen situation. 

Later in the pod, they discuss Merrill Kelly and the Diamondbacks' claims about pitch tipping and sign stealing and share whether Carson Kelly and Miguel Amaya should get a bump in their WAR because of their ABS prowess. The panel wraps up the pod discussing how far back the Cubs need to be from the Brewers to believe they have a shot at winning the division, and discusses the Cubs' 150th anniversary team.

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Pete Crow-Armstrong had an emphatic moment in his 2026 MVP-caliber campaign as he launched a pair of home runs, including a walk-off blast, against the White Sox in the Cubs win in the Crosstown Classic. Andy Martínez, Tony Andracki and Kyle Millinowisch recap the incredible night from PCA and assess what this means for his MVP campaign, especially going up against the Dodgers' Shohei Ohtani. 

The crew then breaks down what Dansby Swanson's oblique injury means to the team, and why they're concerned about, even though he hasn't been hitting as well as he has in the past. Then, they discuss Edward Cabrera's blister that has landed him on the injured list for the second time this season (and his third IL stint overall) and what role, if any, he'll play in 2026. The trio wrap up by discussing whether or not they'd like to see a Crosstown Classic World Series and what that would mean for the the city. 

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Jed Hoyer and the Chicago Cubs showed their aggressiveness this trade deadline, acquiring pitchers Kevin Gausman, Clay Holmes, Ryan Zeferjahn and Braxton Garrett, and outfielder Tyrone Taylor. The front office showed a willingness to try and bolster a roster that has been positive in 2026. Andy Martínez, Tony Andracki and Kyle Millinowisch break down all of the moves a day after the deadline.

The group analyze what this means for a pitching staff that has shown plenty of signs of wear already this season. Then, the group discuss what this means for the Cubs' playoff rotation and why they are now poised to make a deeper run in October.

Lastly, the panel discusses whether the prices they paid, why they're OK with the Cubs moving on from certain prospects and what it means for the future of their player development.

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The MLB trade deadline is rapidly approaching and the Cubs have a very curious situation ahead of them. Do they go all-in and try to target pitchers like Tarik Skubal and Mason Miller?

Andy Martínez, Tony Andracki and Kyle Millinowisch debate the Cubs' approach to the deadline, including laying out their own ideas of what a perfect trade haul would look like to boost this 2026 roster. The panel throws out some key names for fans to watch, including Freddy Peralta, Kevin Gausman and a host of intriguing relievers.

Plus, a unique wrinkle in the MLB rulebook that impacted the Cubs this week and a surprisingly hot-button debate in the baseball world comes to the surface.

The WCB panel also dabbles into other sports, breaking down Patrick Kane's return to Chicago and a mini preview of Bears training camp.

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The Chicago Cubs enter the All-Star Break 12 games over .500 and in a playoff position, but it's arguably been one of the wildest rides to that point. Tony Andracki, Andy Martínez and Kyle Millinowisch assess the team's first half and what the rest of the season may look like for this unpredictable team.

Then, the trio handout some midseason superlatives and awards, including:
- Biggest surprise of the first half
- MVP
- CY Young
- Best offseason move
- Best win
- Worst loss
- Best stat
- 2nd half predictions
- Biggest disappointment

The trio wrap it up with their usual, "That Guy Rocked" segment, a surprising pick that leaves Tony and Andy stumped.

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Pete Crow-Armstrong has been on another level for a month-and-a-half, begging the question: Did the Cubs actually fleece him in the $115 million contract extension they signed him to before the 2026 season?

Crow-Armstrong's hot stretch and eye-popping skillset was a main topic of conversation on the latest Windy City Breakdown Podcast as hosts Tony Andracki, Kyle Millinowisch and Zoe Grossman discussed the Cubs star outfielder.

Plus, what's behind the Cubs' strong play over the last month? And can they catch the Brewers in the NL Central?

The panel also broke down what the Cubs' approach should be at the MLB trade deadline and whether or not Jed Hoyer's front office should go all in.

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The Cubs could put together a very strong pitching staff just with all the guys on the injured list. Ben Brown, Edward Cabrera and key relievers have all landed on the shelf over the last week, putting the Cubs in a bit of a bid.

Andy Martínez, Tony Andracki and Kyle Millinowisch discuss all the pitching injuries on the Windy City Breakdown Podcast and how the Cubs weather the storm. The panel also answers the question -- are the Cubs ... back?

They were the best team in baseball for six weeks, then the worst team in baseball for over a month. And now they've been the best team in baseball again for the last 2-3 weeks. So, who are the real Cubs?

Plus, can David Peterson and Bryse Wilson actually be saviors for the 2026 season? And where should Alex Bregman bat in the Cubs' order?

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The Cubs just finished up the easiest stretch of their schedule, where they went 6-6 against two of the worst teams in baseball (Giants, Rockies). Despite Pete Crow-Armstrong's superstar hot streak, the offense still can't find its way with runners in scoring position and the pitching staff continues to deal with a litany of injuries.

Andy Martínez, Tony Andracki and Kyle Millinowisch welcome Zoe Grossman from Cubs on SI to the Windy City Breakdown Podcast to analyze all the latest with this Cubs team. Should Dansby Swanson's struggles merit less playing time -- especially considering youngsters Matt Shaw and Pedro Ramirez have given the Cubs a boost recently?

And who is the biggest disappointment among offseason additions: Alex Bregman or Edward Cabrera?

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