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

Business of Sports: NFL Business Podcast

NFL Business

Sports News, News

4.7 • 626 Ratings

🗓️ 18 March 2026

⏱️ 53 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

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

Transcript

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0:00.0	Now, are all the traitors present?
0:02.5	Let's get started, shall we?
0:04.5	From rags to riches.
0:05.8	I'm so sick of this.
0:07.0	Working like a dog and being treated worse.
0:09.1	Yorkshire to New York.
0:10.7	Or climbers, you and me.
0:12.4	A life dedicated to revenge.
0:14.4	Let's make this an occasion to remember.
0:16.5	A woman of substance on Channel 4.
0:19.2	Stream now.
0:21.2	You're listening to Draft King's Network.
0:56.2	Thank you. Hey there, boys and girls.
0:59.4	Welcome to another edition of the Business of Sports with Andrew Brand.
1:00.4	I'm your host, Andrew Brand.
1:02.8	We're produced by Jack Connell, the music you hear under me.
1:05.7	That's my son, Sam Brandt, Boy Blue Tunes.
1:12.5	We're presented, as always, by Draft Kings, have a special simulcast business of sports podcast for you this week.
1:17.4	More about me as I was kind of interviewed, but also talked about the news of the week, especially some news about the Packers and a worry, concern, not imminent, but a concern for the future with revenues and access to private equity from other teams, etc.
1:29.6	I'll talk about that in the podcast.
1:32.0	Cliff Stein was a colleague of mine in the NFC North for many years with the Chicago Bears doing what I did, doing contracts, managing the salary cap.
1:41.6	He was with the Bears a lot longer than I was with the Packers,
	...

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