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?

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.

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.

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. Download Cash App Today: capl.onelink.me/vFut/hap8idx8 #CashAppPod. Cash App is a financial services platform, not a bank. Banking services provided by Cash App’s bank partner(s). Prepaid debit cards issued by Sutton Bank, Member FDIC. See terms and conditions at cash.app/legal/us/en-us/card-agreement. Direct deposit and promotions provided by Cash App, a Block, Inc. brand. Visit cash.app/legal/podcast for full disclosures.

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.

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.

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.

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.

After Part 1 of the Thanksgiving mailbag focused on pitching, Sahadev Sharma and Patrick Mooney are back to answer more questions from listeners, focusing primarily on the offense. The Athletic writers acknowledge what could become a huge hole in the lineup, and outline how the front office may respond this winter. Plus more thoughts on young talent and the potential for contract extensions. Follow North Side Territory all offseason for the latest news and notes on the Cubs. Download Cash App Today: capl.onelink.me/vFut/hap8idx8 #CashAppPod. Cash App is a financial services platform, not a bank. Banking services provided by Cash App’s bank partner(s). Prepaid debit cards issued by Sutton Bank, Member FDIC. See terms and conditions at cash.app/legal/us/en-us/card-agreement. Direct deposit and promotions provided by Cash App, a Block, Inc. brand. Visit cash.app/legal/podcast for full disclosures. Take advantage of Ridge’s Biggest Sale of the Year and GET UP TO 47% OFF by going to Ridge.com/FOUL #Ridgepod

The baseball industry does not shut down during Thanksgiving week. As the Cubs continue to scour the pitching market, Sahadev Sharma and Patrick Mooney sit down to answer good questions from listeners. The Athletic writers share some of the names they’re hearing, in terms of bullpen targets. Plus a breakdown of the Phil Maton deal and some trade possibilities. Listen to North Side Territory throughout the offseason for the latest developments around the Cubs. Go to MeUndies.com/foul and enter promo code foul for up to 50% off! Take advantage of Ridge’s Biggest Sale of the Year and GET UP TO 47% OFF by going to Ridge.com/FOUL #Ridgepod

With the offseason activity beginning to pick up in that window after the GM meetings and before Thanksgiving, The Athletic’s Sahadev Sharma and Patrick Mooney focus on the two players who received qualifying offers from the Cubs. Imanaga will return to Wrigley Field on a one-year, $22.025 million contract while the Cubs are positioned to get a draft pick if/when Tucker signs with a different team. What does Imanaga’s decision mean for the current baseball budget and the club’s overall offseason goals? And how will the Cubs somehow replace Tucker and get better next season? Listen to North Side Territory all winter for the latest on the Cubs. Go to MeUndies.com/foul and enter promo code foul for up to 50% off! Receive 30% off the 1st year of any annual Baseball America subscription using our code NorthSide30.

Do the Cubs have enough young talent to sustain a perennial playoff contender? Geoff Pontes joins the show to discuss his top-10 rankings of the organization’s best prospects. In a wide-ranging conversation with The Athletic’s Sahadev Sharma and Patrick Mooney, the Baseball America writer shares his reporting on the farm system’s pitching deficit, as well as perspectives on the hitters who can move quickly toward Wrigley Field and the trade chips potentially on the table. Get 15% off The Perfect Jean with the code FOUL15 at theperfectjean.nyc/FOUL15 #theperfectjeanpod

Back from Las Vegas, Sahadev Sharma and Patrick Mooney compare notes after roaming The Cosmopolitan this week, trying to track down information on the Cubs. The two writers from The Athletic share what they heard and observed at the sport’s offseason kick-off event. Included in this episode: names the Cubs are targeting in free agency, an overall assessment of the pitching market and an update on the club’s bullpen strategy. Follow North Side Territory all winter for the latest news surrounding the Cubs. Get Huel for 15% off for New Customers only with code FOUL at Huel.com/FOUL (Minimum $75 purchase)

The Athletic’s Sahadev Sharma and Patrick Mooney are in Las Vegas for Major League Baseball’s GM meetings, reporting on the latest developments with the Cubs. At this traditional starting point for the offseason, the Cubs are signaling their intentions to think big with their pitching staff, not ruling out the top free agents. Listen to North Side Territory for a rundown on those early targets, the mood within the front office and the layers to the Shota Imanaga decisions. Check out square.com/go/FOUL and go support your favorite neighborhood spot to see what Square has been up to in your neck of the woods.

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. Get Huel for 15% off for New Customers only with code FOUL at Huel.com/FOUL (Minimum $75 purchase)

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. Head to Superpower.com and use code TAKE20 at checkout for $20 off your membership. Live up to your 100-Year potential. #superpowerpod

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. Presented by FOX One: Start your 7-day free trial today at FOXone.com Download the DraftKings Sportsbook app and use code FOUL, bet $5 and get $300 in bonus bets if your bet wins.

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. Presented by FOX One: Start your 7-day free trial today at FOXone.com Go to Superpower.com to learn more and lock in the special $199 price while it lasts. Live up to your 100-Year potential. #superpowerpod Check out square.com/go/FOUL and go support your favorite neighborhood spot to see what Square has been up to in your neck of the woods.

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. Download the DraftKings Sportsbook app and use code FOUL, bet $5 and get $300 in bonus bets if your bet wins. Presented by FOX One: Start your 7-day free trial today at FOXone.com