About this episode

Jon Lester joins the show to discuss his experiences and insights on the Chicago Cubs and the Wrigley Field atmosphere.

Big show announcement: Jon Lester, a three-time World Series champion, will be making regular appearances as a special guest analyst on North Side Territory. In his debut episode with The Athletic’s Sahadev Sharma and Patrick Mooney, Lester talks about the 10-year reunion tour for his 2016 teammates, what made that championship club so special and how it compares to this year’s squad. Lester also explains what Alex Bregman is going through as a big free agent in a new city, the importance of clubhouse chemistry and how to approach this roller-coaster season. Use our code for 10% off your next order of MLB tickets on SeatGeek*: seatgeek.onelink.me/RrnK/TERRITORY10 Sponsored by SeatGeek. *Restrictions apply. Max $20 discount 🌶️ See omnystudio.com/listener for privacy information.

People in this episode

Hosts: Sahadev Sharma, Patrick Mooney

Guest: Jon Lester

Topics covered

• Wrigley Field experience
• Chicago Cubs
• 2016 World Series
• clubhouse chemistry
• MLB season

Keywords

• Jon Lester
• Chicago Cubs
• Wrigley Field
• 2016 World Series
• Alex Bregman
• clubhouse chemistry
• MLB tickets

Sponsors

SeatGeek

Mentioned in this episode

Organizations: The Athletic

More episodes of North Side Territory: A Chicago Cubs Podcast

• What we’re hearing about the Cubs: 2016 reunion, trade chips, deadline priorities · July 20, 2026 · 34 min
• The prospects and draft decisions shaping the Cubs’ trade deadline and future · July 18, 2026 · 29 min
• Trade deadline reset: How the Cubs are positioned out of the All-Star break · July 17, 2026 · 26 min
• Jon Lester’s All-Star break outlook: Storylines, 10-year reunion and more · July 14, 2026 · 31 min
• Three X-factors for the Cubs after the All-Star break · July 12, 2026 · 27 min
• What we’re hearing about the Cubs before the All-Star break: Trade deadline thoughts and more · July 11, 2026 · 27 min

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