North Side Territory: A Chicago Cubs Podcast

The World Series is over and the Brewers are champions for the first time. It is not a great look for the big-market franchise located roughly 90 miles from Milwaukee. But the Cubs have a huge opportunity to reshape their club before Major League Baseball’s widely anticipated lockout. Now that the offseason is officially here, The Athletic’s Sahadev Sharma and Patrick Mooney look at The Brewers Way, how the Cubs approached the last pre-lockout frenzy and why they stepped up to retain a key hitting coach for Pete Crow-Armstrong.

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As Milwaukee enjoys the World Series drama, the Cubs are trying to revamp their pitching systems and prepare for a pivotal offseason. Before the Hot Stove action begins, The Athletic’s Sahadev Sharma and Patrick Mooney set the scene by answering questions from listeners. The focus is, obviously, on Chicago’s issues with pitching development and why the Brewers are light years ahead of their big-market rivals.

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Money can’t fix everything with this team. As much as the Cubs need to spend on free agents and make trades this offseason, internal improvements will also have to happen. Closing the gap on the Brewers and making a deeper postseason run will require certain players stepping up next year. The Athletic’s Sahadev Sharma and Patrick Mooney give you five names to consider, with reasons for (and against) optimism.

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While the focus should be on the World Series, the baseball industry is also going through the hiring-and-firing season for coaches and executives. The Athletic’s Sahadev Sharma and Patrick Mooney give you the details on what this means in Wrigleyville. Their reporting provides details on Jared Banner taking a GM job in Baltimore, the Mets looking at Pete Crow-Armstrong’s personal hitting coach and the Cubs running it back with their pitching coaches. Plus more on an outside-the-box candidate in Seattle’s manager search and the Cubs hiring an international scout away from the Rays.

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While pitching remains the clear focus for the Cubs, the organization will still need to make additions to a strong group of position players. The Athletic’s Sahadev Sharma and Patrick Mooney preview where the Cubs could be heading this offseason, giving you five names to know plus an overview of the upcoming free-agent market and the current shape of the roster.

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Everyone knows what Jed Hoyer’s front office will be focused on this offseason. It’s pitching, pitching and more pitching. But who, exactly, should the Cubs be pursuing? Faced with the possibility of having to rebuild their entire starting rotation, there is one obvious name that stands out at the top. The Athletic’s Sahadev Sharma and Patrick Mooney lay out their early read on the Tarik Skubal situation, and then share more names to know before the Hot Stove heats up.

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Changes are definitely coming to this roster, but the Cubs won’t be starting from scratch. Besides a core group of players, the club also has decisions to make on upcoming free agents who may have strong interest in a reunion. The Athletic’s Sahadev Sharma and Patrick Mooney explain why Clay Holmes and David Peterson would make a lot of sense in the 2027 rotation. Plus, a full breakdown of Chicago’s catching situation, with Carson Kelly eligible to become a free agent. Are Miguel Amaya and Owen Ayers ready to take over behind the plate?

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While the Cubs are in offseason planning mode, the Dodgers and Brewers are back in the National League Championship Series. Pitching is always a focus in October, and that remains the challenge for an organization that will have to almost entirely rebuild the rotation as well as the bullpen. With that in mind, The Athletic’s Sahadev Sharma and Patrick Mooney break down who they think won’t be returning to Wrigley Field with the 2027 Cubs.

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Within every end-of-season briefing with the Chicago media, the Cubs’ top baseball executive always has a few talking points, some things you might not have thought of before, and bigger ideas and themes that will shape the club’s planning and internal messaging. The Athletic’s Sahadev Sharma and Patrick Mooney interpret what they heard in the Wrigley Field interview room and explain what it means going forward.

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What just happened? Yes, the Cubs looked a little shaky near the end of the regular season, but the Padres absolutely dominated this Wild Card Series from start to finish. The Athletic’s Sahadev Sharma and Patrick Mooney provide insights and information directly from the clubhouse at Petco Park. Listen to find out how the club’s stars were processing the end, why the Padres were a bad matchup and where this big-market franchise goes from here.

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What a clunker to open this Wild Card Series in San Diego. The Cubs looked overmatched in every phase of Game 1 as the Padres pushed them to the brink of playoff elimination. The Athletic’s Sahadev Sharma and Patrick Mooney share their reporting and insights from Petco Park, where the Cubs definitely won’t get any kind of home-field advantage. How does Chicago’s pitching plan line up for Game 2? What’s the current mood in the clubhouse? Where does the turnaround begin? We’re about to find out.

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What a finish to the regular season — Alex Bregman’s freak accident, Pete Crow-Armstrong’s 40-40 moment, a clinch party in Wrigleyville, a last-minute doubleheader at Fenway Park and a detour to Florida. It all leads into another wild-card series against the Padres. Before the Cubs travel to San Diego, The Athletic’s Sahadev Sharma and Patrick Mooney share what they’re hearing and seeing. Should you be concerned about the offense? Is the bullpen actually in a better place? Who’s in the playoff rotation? Listen for an early preview of a must-see matchup.

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Bregman Watch is on. In an unexpected, overwhelmingly positive update — under the circumstances — the Cubs expressed their belief that the All-Star third baseman will play again this year, and maybe even during the final weekend of the regular season. The Athletic’s Sahadev Sharma and Patrick Mooney interpret this news and also share some of their late-season takeaways from Wrigley Field.

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Even with their magic number to clinch a postseason spot cut down to one, the Cubs weren’t necessarily in a celebratory mood. The Bregman moment was that unsettling, and his presence is that important to the team. The Athletic’s Sahadev Sharma and Patrick Mooney share what they heard and saw in Cincinnati, including an interesting update on how the Cubs are already running their bullpen in playoff mode.

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The magic number is dwindling to a point where the Cubs will almost certainly qualify for the playoffs. Maybe it doesn’t matter how they get there. But heading into the final week of the regular season, it’s easy to spot the areas of concern. You also have to acknowledge the good things that put them in this position. The Athletic’s Sahadev Sharma and Patrick Mooney break it all down, including a full report on the team field trip to Churchill Downs that Alex Bregman and Craig Counsell helped organize.

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Pete Crow-Armstrong appears to be a lock for National League MVP. Alex Bregman continues to show why he was such a coveted free agent. And Shota Imanaga is locked in again. The Cubs would be rolling into the playoffs — if their bullpen wasn’t such a big question mark. The Athletic’s Sahadev Sharma and Patrick Mooney break it all down after a big series win over the first-place Braves.

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The next two weeks will define the Cubs’ season. Making the playoffs is an annual goal that remains within reach, even a likely outcome. But until the first bottle of champagne is popped, the Cubs are going to have to sweat it out with the Phillies, Padres and Diamondbacks. The Athletic’s Sahadev Sharma and Patrick Mooney break down the state of play in the middle of September. Missing the playoffs would be an organizational failure that wastes Pete Crow-Armstrong’s likely MVP season, the best defense in baseball and the sport’s highest-scoring offense. Stay tuned.

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With the Cubs getting swept out of Milwaukee, it seems like a good time to hear what the fans are thinking. The Athletic’s Sahadev Sharma and Patrick Mooney answer questions from listeners who want to know: Are Cubs officials as frustrated as Cubs fans when the Brewers are running away with the division title again? Moving forward, how will this late-season slump influence the organization’s strategies around pitcher development and bullpen construction? And is anyone coming from Triple-A Iowa to help this team? Listen for behind-the-scenes insights and the latest information on the Cubs.

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With the playoffs fast approaching, the Cubs are running out of time to fix their bullpen. The available relief options are also limited in the middle of September. What’s the current mood in the clubhouse? How did it get to this point? And who might be able to help with these issues? The Athletic’s Sahadev Sharma and Patrick Mooney share their reporting and insights from Milwaukee.

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Another tough loss in Milwaukee spotlighted the gap in the division as well as the manager’s decisions. The Athletic’s Sahadev Sharma and Patrick Mooney explain what Craig Counsell was thinking and where the Cubs go from here. Within the next three weeks, the Cubs have to figure out their bullpen, finish ahead of the Phillies and try to peak at the right time. Because the Brewers are clearly the class of the NL Central over a 162-game schedule. The playoffs might be a different story.

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