Looking ahead to a new season, The Athletic’s Sahadev Sharma and Patrick Mooney see a playoff-caliber team that’s approaching a cliff. With so many key players close to reaching free agency – and questions about the farm system and the baseball budget – this should be a fascinating year around the Cubs. Who stays? Who goes? What’s different from the organization’s last cliff? And why do some of these issues sound familiar?

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Happy holidays from North Side Territory. With a playoff season in the books and the offseason in full swing, The Athletic’s Sahadev Sharma and Patrick Mooney sit down to reflect on the last 12 months on the Cubs beat. From Pete Crow-Armstrong becoming a star to Craig Counsell putting his stamp on the organization to the crowds reenergizing Wrigley Field, there was no shortage of topics to cover. We’re also left to wonder when the Cubs will make their next big move and act like the big-market team that those fans deserve.

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The Cubs are rebuilding their bullpen without Keller, who authored a comeback story at Wrigley Field that landed him a two-year, $22 million contract with the Phillies. The Athletic’s Sahadev Sharma and Patrick Mooney give you their takeaways from Keller’s bounce-back season, and how that applies to the Cubs moving forward. This is also a chance to get to know vice president of pitching Tyler Zombro, a key behind-the-scenes figure whose influence is growing.

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Reacting to Michael King’s deal with the Padres, Sahadev Sharma and Patrick Mooney map out where the Cubs could go from here. The two beat writers from The Athletic share what they heard on King, as well as their insights on Tatsuya Imai and Zac Gallen, two other starters who have been repeatedly linked to the Cubs. Is it time to be concerned yet? Listen to North Side Territory for the latest offseason news, notes and analysis.

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After leaving baseball’s annual convention, The Athletic’s Sahadev Sharma and Patrick Mooney are back from Orlando and ready to share the information they gathered on the Cubs. How is the front office remaking the bullpen for Craig Counsell? What’s the deal with the Nico Hoerner trade rumors? And is a playoff contender really prepared to let Kyle Tucker walk as a free agent and replace him with rookies Owen Caissie and Moisés Ballesteros? Listen to North Side Territory all winter for the latest information, insight and analysis.

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Checking in from Orlando, The Athletic’s Sahadev Sharma and Patrick Mooney share what they’ve been hearing about the Cubs’ various offseason pursuits. Matt Shaw has been a discussed name at Major League Baseball’s Winter Meetings, but the Cubs seem intent on building around him and continuing their youth movement. Where does that leave the Cubs with Alex Bregman and their objective to acquire more pitching? And why has there been a relative lack of activity across the baseball industry? Follow North Side Territory all winter for the latest news and notes.

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Before traveling to Orlando for baseball’s annual offseason convention, Sahadev Sharma and Patrick Mooney share what they’re hearing about the Cubs and where the expectations should be set right now. The two beat writers from The Athletic are reporting that the Cubs are back in the mix for Alex Bregman. What does that mean for Matt Shaw and the club’s wide-ranging search for pitching? Find out on North Side Territory, the place for the latest news on the Cubs all offseason.

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With the Winter Meetings approaching, The Athletic’s Sahadev Sharma and Patrick Mooney sit down to compare notes on the Cubs’ approach to the free-agent market. Kyle Tucker visiting the Blue Jays’ complex in Florida is yet another sign that he’s planning to play somewhere else next year. The Cubs, however, have not ruled out adding another hitter and spending for impact free agents. Their pursuit of Dylan Cease — before he signed with Toronto — is telling. Find out why on North Side Territory, the show for offseason news and analysis of the Cubs.

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