North Side Territory: A Chicago Cubs Podcast

Latest Episodes:

Five Cubs who should be back next season Oct 09, 2026

Show notes

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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Five Cubs who won’t be back next season Oct 08, 2026

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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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For Cubs president Jed Hoyer, the offseason agenda is clear: Add a ton of pitching, catch up to Brewers Oct 03, 2026

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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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The End: Cubs’ season is over after no-show performance in playoffs Oct 01, 2026

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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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With Cubs on brink of elimination, we’ll see how resilient they really are Sep 30, 2026

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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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As Cubs limp into playoff rematch with Padres, a look at what matters now (and what doesn’t) Sep 27, 2026

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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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What we’re hearing about Alex Bregman and the Cubs’ playoff planning Sep 23, 2026

Show notes

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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Alex Bregman’s freak injury clouds the Cubs’ playoff picture Sep 21, 2026

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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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Cubs are on the verge of clinching a playoff spot, but are they trending in the right direction? Sep 19, 2026

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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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With offense/defense clicking, Cubs have everything except their bullpen in order for playoffs Sep 17, 2026

Show notes

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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