Cliff Stein: Former Senior Vice President and General Counsel for the Chicago Bears

Cliff Stein: Former Senior Vice President and General Counsel for the Chicago Bears

From Business of Sports: NFL Business Podcast by NFL Business

March 18, 2026 · 54 min

About this episode

Cliff Stein discusses his career and insights on NFL negotiations with Andrew Brandt.

On this week's Business of Sports, Andrew Brandt is joined by former Senior Vice President and General Counsel for the Chicago Bears, Cliff Stein, to discuss Andrew's career, his transition from professional sports to college, cash vs. cap, how they both handled negotiations in the NFL, and more! Check out Cliff's podcast, "Negotiation Warriors", here: https://podcasts.apple.com/us/podcast/negotiation-warriors/id1876984454 Sign up & find more details for Andrew's symposium here: https://www.villanova.edu/university/law/about/news-events/events/2026/0224.html Download the DraftKings Sports Book App and use code ROSS Connect with the Pod Website - https://www.rosstucker.com Become A Patron - https://www.patreon.com/RTMedia Podcast Twitter - https://twitter.com/RossTuckerPod Podcast Instagram - https://www.instagram.com/rosstuckerpod/ Ross Twitter - https://twitter.com/RossTuckerNFL Learn more about your ad choices. Visit podcastchoices.com/adchoices

People in this episode

Host: Andrew Brandt

Guest: Cliff Stein

Topics covered

  • NFL negotiations
  • sports law
  • career transition
  • cash vs. cap
  • sports management

Keywords

  • Cliff Stein
  • Andrew Brandt
  • NFL
  • negotiations
  • sports law
  • Chicago Bears
  • cash vs. cap

Sponsors

DraftKings

Mentioned in this episode

Organizations: Chicago Bears, Negotiation Warriors

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