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Negotiation Warriors

Negotiation Warriors

De : Cliff M. Stein
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Negotiation Warriors, the podcast that features conversations with the greatest negotiators in professional sports.

© 2026 Negotiation Warriors Economie
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  • Episode 020: "You Don't Look Like an Agent" - Adopting a Persistent Mindset (Kim Miale)

    Episode 020: "You Don't Look Like an Agent" - Adopting a Persistent Mindset (Kim Miale)
    Oct 26 2026
    Send us Fan Mail"You Don't Look Like an Agent" - Adopting a Persistent Mindset with Kim Miale At her first NFL Combine, a scout looked at Kim Miale and told her:"You don't look like an agent." Her response was simple: "What's an agent look like?"That exchange reflected the stereotypes Kim would encounter as a woman entering one of the most competitive and traditionally male-dominated industries in professional sports.But Kim Miale wasn't about to let someone else's expectations define what she could accomplish. She had already passed the NFL agent exam, applied to agencies across the country without receiving a single response, and begun building her career from the ground up with little more than business cards bearing her apartment address and cell phone number.Years later, an unexpected phone call would change everything.Jay-Z had launched Roc Nation Sports, and the agency needed someone to recruit quarterback Geno Smith. Kim answered the call.In Episode #020 of Negotiation Warriors, I sit down with Kim Miale, NFL agent and General Counsel of Roc Nation Sports, whose remarkable journey from an aspiring agent struggling to break into the industry to one of the NFL's most accomplished negotiators is a powerful example of persistence, preparation, and believing in yourself.Kim became Roc Nation Sports' first in-house agent and went on to represent some of the biggest names in professional football, including Saquon Barkley, Geno Smith, Ronnie Stanley, JuJu Smith-Schuster, and Dez Bryant.In 2018, she made history when Saquon Barkley became the highest-drafted NFL player ever represented by a female agent, selected second overall. She also negotiated a landmark contract extension for Baltimore Ravens offensive tackle Ronnie Stanley that, at the time, included the most guaranteed money ever awarded to an offensive lineman.But this conversation isn't just about football.It's about persistence.It's about resilience.It's about creating opportunities when doors remain closed.It's about earning trust and building relationships.And it's about understanding that becoming a great negotiator requires more than negotiating the biggest contracts.Throughout our conversation, Kim shares the lessons she's learned overcoming rejection, breaking barriers, building a successful career in professional sports, and negotiating hundreds of millions of dollars in NFL player contracts.IN THIS EPISODE, YOU'LL LEARN:• How NFL agent Kristen Kuliga inspired Kim to pursue a career in professional sports representation—and why seeing someone succeed can give others the confidence to follow.• Why Kim refused to abandon her dream after applying to agencies across the country without receiving a single response.• How representing an undrafted prospect helped her develop the persistence, resourcefulness, and relationships necessary to succeed as an NFL agent.• What happened when an NFL scout told Kim, "You don't look like an agent," and how she navigated the stereotypes facing women in professional sports.• How a newspaper article diminishing her accomplishments fueled her determination to prove herself.• The remarkable story of the unexpected phone call that brought her to Roc Nation Sports to recruit Geno Smith—and how that opportunity changed the trajectory of her career.• What makes Jay-Z's Roc Nation Sports different from other major sports agencies and why its athlete-first philosophy places such importance on personal relationships and individualized representation.• Why Kim devoted an entire recruiting season to signing Saquon Barkley, attending every Penn State game and putting all her eggs in one basket.• How she made history representing the No. 2 overall selection in the NFL Draft—and the role trust played in building her relationship with Saquon and his family.• Why honesty, transparency, and trust are the foundation of Kim's negotiating philosophy - and why she believes a negotiator's word should mean everything.• Why negotiating with your own client can be just as challenging as negotiating with an NFL team, particularly when managing expectations about player value and contract compensation.• Why successful agents must be willing to tell clients what they need to hear, not simply what they want to hear.• How preparation, timing, leverage, and understanding the priorities and pressure points of both sides can influence the outcome of a negotiation.• Why mentorship matters - and how Kim is helping create opportunities for the next generation of women pursuing careers in professional sports.Kim also shares her thoughts on leadership, managing expectations, building credibility, overcoming adversity, and why lasting success depends on developing relationships grounded in trust and integrity.Whether you're an executive, attorney, coach, agent, entrepreneur, student, or someone striving to succeed in a competitive profession, this episode offers timeless lessons on persistence, leadership, ...
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    36 min
  • Episode #019: The Humble Negotiator with Mike Greenberg (Tampa Bay Buccaneers)

    Episode #019: The Humble Negotiator with Mike Greenberg (Tampa Bay Buccaneers)
    Oct 5 2026

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    Negotiation Warriors - Episode #019: THE HUMBLE NEGOTIATOR with Mike Greenberg

    Mike Greenberg has spent 16 years with the Tampa Bay Buccaneers, quietly becoming one of the NFL’s most respected front-office and salary-cap executives. He has helped negotiate and manage billions of dollars in player contracts, build a Super Bowl champion, and navigate some of the most complex roster and salary-cap challenges in professional sports.

    Yet throughout his career, Greenberg has remained remarkably humble,consistently sharing the credit with the people around him.

    In Episode 019 of Negotiation Warriors, Cliff Stein sits down with the Buccaneers Assistant General Manager for a rare behind-the-scenes conversation about his journey, his approach to negotiation, and the decisions that helped shape one of the NFL’s most successful organizations.

    Greenberg shares his unconventional path into the NFL—from Hofstra Law School to internships with the New York Jets and NFL Management Council, and ultimately to Tampa Bay in 2010.

    He also tells the remarkable inside story of signing Tom Brady during the early days of COVID. With Brady in New York and Greenberg unwilling to risk waiting another day, he called his brother-in-law Jake and sent him directly to Brady’s apartment with the contract. Jake got Brady’s signature and returned the executed deal to Tampa Bay—because, as Greenberg explains, he wasn’t going to let another minute go by without getting Brady signed.

    Greenberg also pulls back the curtain on the art and science of NFL salary-cap management—cash versus cap, proration, dead money, and the strategy that gave Tampa Bay the flexibility to go “all in” during its championship window.

    And after winning Super Bowl LV, Greenberg and the Buccaneers faced another enormous challenge: How do you keep the band together? Greenberg takes listeners inside the creativity, collaboration and ownership commitment required to retain the core of a championship roster even as the NFL salary cap declined.

    Finally, Greenberg shares the lessons he has learned at the negotiating table: listen to the other side, understand their position, be fair when you have leverage, anticipate their arguments and never underestimate preparation.

    IN THIS EPISODE:

    • Greenberg’s unconventional path into the NFL
    • How law school shaped him as a negotiator
    • The inside story of signing Tom Brady
    • Cash vs. cap, proration and dead money
    • How Tampa Bay went “all in” to build and preserve a championship roster
    • Working alongside Jason Licht and Jackie Davidson
    • Why great leaders acknowledge mistakes
    • How Greenberg prepares for negotiations
    • Why listening, fairness and preparation matter when leverage shifts

    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

    Subscribe to Negotiation Warriors for more conversations with the executives, agents, attorneys and dealmakers behind some of the biggest negotiations in professional sports.

    #NegotiationWarriors #MikeGreenberg #TampaBayBuccaneers #TomBrady #NFL #NFLContracts #SalaryCap #Negotiation
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    44 min
  • Episode #018: From Apprentice to Mentor (Andrew Kessler)

    Episode #018: From Apprentice to Mentor (Andrew Kessler)
    Sep 21 2026

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    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
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    55 min
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