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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