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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