Episode #18
Episode #018: From Apprentice to Mentor (Andrew Kessler)
Send us Fan Mail Episode #018 — From Apprentice to Mentor with Andrew Kessler What does it take to become one of the most respected agents and negotiators in professional football? For Andrew Kessler, the education started long before he negotiated his first NFL contract. On Episode #018 of Negotiation Warriors, Cliff Stein sits down with veteran NFL agent Andrew Kessler of Athletes First for a fascinating conversation about mentorship, creativity, relationships, preparation and the lessons learned over two decades negotiating NFL player contracts. Andrew grew up with a front-row seat to the sports industry as the son of renowned sports law attorney Jeffrey Kessler. But when he decided to become an agent, he began his education in the business working under legendary NFL agent Tom Condon - sitting in on negotiations, listening, observing and learning the craft from one of the best to ever do it. Those lessons helped Andrew develop his own approach to representing players and negotiating contracts. Over the course of his career, he has been part of negotiating more than $1 billion in NFL contracts, including work on landmark quarterback deals involving Peyton Manning and Eli Manning, and more recently negotiating the contracts for Green Bay Packers quarterback Jordan Love, and Indianapolis Colts quarterback Daniel Jones. Andrew takes us behind the scenes of one of the most creative contracts in NFL history - the Steve Hutchinson “poison pill” offer sheet—and tells the remarkable story of how, early in his career, he came up with the idea for a contract provision designed to make it virtually impossible for Seattle to match Minnesota's offer. He also discusses the creative rookie contract structure for QB Drew Henson with the Dallas Cowboys. But Andrew's story eventually comes full circle. Years after Tom Condon gave him the opportunity to learn the business by observing negotiations firsthand, Andrew found himself mentoring a young David Mulugheta, who would go on to become one of the NFL's most successful agents. Andrew explains how he consciously tried to give David the same kind of education and mentorship that Tom had given him - passing along the lessons and experiences he had been fortunate enough to receive. Along the way, Andrew shares what he has learned about preparing for high-stakes negotiations, understanding leverage, reading the person across the table, knowing when statistics matter - and when they don't- and building strong relationships with NFL front offices while remaining a passionate advocate for his players. He also explains why understanding the other side doesn't mean agreeing with them. It means recognizing their circumstances, understanding the constraints they are operating under, and finding creative ways to reach an agreement that works for both sides. This episode is an inside look at how an NFL agent learns the craft, develops his own negotiating style, builds a career based on relationships and creativity, and ultimately passes those lessons on to the next generation. And when asked about his approach to negotiation, Andrew distills it into a simple lesson: “Winning is finding agreement that works for both.” ️ Negotiation Warriors — Conversations with the Greatest Negotiators in Professional Sports. Hosted by Cliff Stein Former Chicago Bears SVP & General Counsel | NFL Contract Negotiator | Sports Attorney | Negotiation Strategist
