North Side Territory: A Chicago Cubs Podcast

Latest Episodes:

Brad Keller gets paid while the Cubs go in a different direction Dec 20, 2025

Show notes

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.

Two easy ways to support the show: Leave us a nice rating/review here and SUBSCRIBE to NST on Youtube!

See omnystudio.com/listener for privacy information.

Where are the Cubs in their pursuit of another starting pitcher? Dec 19, 2025

Show notes

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.

Two easy ways to support the show: Leave us a nice rating/review here and SUBSCRIBE to NST on Youtube!

See omnystudio.com/listener for privacy information.

Cubs takeaways from the Winter Meetings Dec 12, 2025

Show notes

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.

Two easy ways to support the show: Leave us a nice rating/review here and SUBSCRIBE to NST on Youtube!

See omnystudio.com/listener for privacy information.

What have the Cubs been up to at the Winter Meetings? Dec 10, 2025

Show notes

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.

Two easy ways to support the show: Leave us a nice rating/review here and SUBSCRIBE to NST on Youtube!

See omnystudio.com/listener for privacy information.

Winter Meetings Preview: Will the Cubs make a splash? Dec 05, 2025

Show 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.

Two easy ways to support the show: Leave us a nice rating/review here and SUBSCRIBE to NST on Youtube!

See omnystudio.com/listener for privacy information.

What we’re hearing about the Cubs, free agents and spending Dec 04, 2025

Show notes

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.

Two easy ways to support the show: Leave us a nice rating/review here and SUBSCRIBE to NST on Youtube!

See omnystudio.com/listener for privacy information.

Cubs mailbag: How will the team replace Kyle Tucker? Nov 27, 2025

Show notes

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.

Take advantage of Ridge’s Biggest Sale of the Year and GET UP TO 47% OFF by going to Ridge.com/FOUL #Ridgepod

Two easy ways to support the show: Leave us a nice rating/review here and SUBSCRIBE to NST on Youtube!

See omnystudio.com/listener for privacy information.

Cubs offseason mailbag: Pitching names to know Nov 25, 2025

Show notes

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

Two easy ways to support the show: Leave us a nice rating/review here and SUBSCRIBE to NST on Youtube!

See omnystudio.com/listener for privacy information.

What’s next for Shota Imanaga and Kyle Tucker? Nov 20, 2025

Show notes

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.

Two easy ways to support the show: Leave us a nice rating/review here and SUBSCRIBE to NST on Youtube!

See omnystudio.com/listener for privacy information.

In-depth look at Baseball America’s top Cubs prospects Nov 18, 2025

Show notes

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

Two easy ways to support the show: Leave us a nice rating/review here and SUBSCRIBE to NST on Youtube!

See omnystudio.com/listener for privacy information.