Episode 001: The Origin of Negotiation Warriors

In the first full episode of Negotiation Warriors, Doug Pires and Jessica DeBear of the Stopping By Podcast interview Cliff Stein about the origin of the podcast and the mindset behind great negotiators in professional sports. Drawing from more than 30 years in the NFL — as both an agent and General Counsel of the Chicago Bears — Cliff shares lessons on preparation, tactics, discipline, and the psychology of high-stakes negotiations.

What does it mean to be a Negotiation Warrior?

This episode lays the foundation for future conversations with elite negotiators across sports and business.

Introduction to Negotiation Warriors. Hosted by Cliff Stein.

Every negotiation is an opportunity to learn.

After more than two decades negotiating NFL player contracts and managing the salary cap, I realized something powerful: every conversation across the table — with agents, executives, players, and owners — was a masterclass in leverage, preparation, psychology, and strategy.

In this introductory episode of Negotiation Warriors, I share the journey behind the podcast — from my years inside NFL front offices to teaching The Art of the Player Contract Negotiation at Northwestern and Miami Law — and why I created this platform.

This podcast pulls back the curtain on the player contract ecosystem and features conversations with some of the greatest negotiators in professional sports. We’ll explore their philosophies, tactics, turning points, and the mindset that separates good negotiators from elite ones.

If you want to understand how deals really get done at the highest level — this is where the education continues.

Welcome to Negotiation Warriors.