With the offseason underway, The Athletic’s Sahadev Sharma and Patrick Mooney break down the latest happenings around a Cubs team that will be very busy this winter. What did Pete Crow-Armstrong learn from his Gold Glove-winning season? How will Jed Hoyer’s front office rebuild a bullpen almost entirely from scratch? And why do these early offseason moves seem overly conscious of the budget? Listen to North Side Territory, which will be in Las Vegas for next week’s GM meetings.

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The Cubs made their first major offseason move by declining a three-year option to extend Shota Imanaga’s contract. In turn, the Japanese pitcher declined his player option for next season and elected to become a free agent. The Athletic’s Sahadev Sharma and Patrick Mooney bring you both sides of this story, explaining why Chicago’s front office made this decision and how Imanaga will explore his options. What is the next move for the Cubs? And where does Imanaga go from here? Follow North Side Territory all offseason for the latest news and notes.

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With the World Series nearing a conclusion, The Athletic’s Sahadev Sharma and Patrick Mooney take questions from listeners to give Cubs fans a preview of what to expect this winter. This edition of the mailbag gives insights into Jed Hoyer’s front office, the shape of the 2026 pitching staff and which players might be up for a contract extension. Follow North Side Territory all offseason for the latest news and notes on the Cubs.

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The Cubs are probably going to pour their resources into the pitching staff this offseason. Without making any moves, the club could right now put together a competitive 2026 Opening Day lineup. But where’s the fun in that? The Athletic’s Sahadev Sharma and Patrick Mooney go over the names you need to know this winter – and there are several familiar faces on this list of hitters with the potential to take the Cubs to the next level.

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Already shifting into offseason mode, it’s not too early to start thinking about which pitchers the Cubs will be targeting this winter, both via trades and the free-agent market. The Athletic’s Sahadev Sharma and Patrick Mooney give you five names to consider, based on their reporting and institutional knowledge, as well as the reasons why (or why not) they would fit into the organization’s plans. After a shortened playoff run that exposed some issues with Chicago’s pitching staff, this will be a clear area of focus.

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After winning a playoff round and then losing to a small-market rival, the Cubs are trying to build a team for the next level, which would mean finishing ahead of the Brewers in the division and seriously competing for a World Series trophy. Changes to the roster are inevitable. The Athletic’s Sahadev Sharma and Patrick Mooney give you their best guesses on who won’t be back, and how the front office is looking at this offseason opportunity.

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After processing Jed Hoyer’s entire end-of-season news conference, The Athletic’s Sahadev Sharma and Patrick Mooney share their latest takeaways. The answers (and non-answers) from Chicago’s president of baseball operations were telling. The Wrigley Field interview room provided a good snapshot of where the Cubs are as an organization (and where they still have to go). The offseason will revolve around Shota Imanaga’s complicated contract decisions, a rebuild of the pitching staff and the Kyle Tucker situation. North Side Territory will have it all covered.

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The Athletic’s Sahadev Sharma and Patrick Mooney take you inside the visiting clubhouse in Milwaukee, where Cubs players processed the disappointing end to a good (but not great) season. What happened against the Brewers? How is there a chance that Kyle Tucker comes back to Wrigley Field? And where does the front office turn its focus now? Listen to North Side Territory throughout the offseason for the latest information.

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