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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.

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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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Negotiation Warriors, Episode #017 - LIFE ON THE NFL BUBBLE with Maema Njongmeta

What is it really like to live on the NFL bubble?

Every year, hundreds of NFL players fight to earn a spot on the 53-man roster. Careers can change overnight. A player can make the team, contribute on Sundays, get released, land on a practice squad, get another opportunity - or suddenly find himself at home waiting for the phone to ring.

Maema Njongmeta is living that reality right now. After going undrafted in 2024, he beat the odds to make the Cincinnati Bengals' 53-man roster, later joined the Carolina Panthers and became a significant special-teams contributor. Following the 2026 preseason, Carolina released him. Today, Maema is a healthy NFL free agent - training, staying ready and waiting for his next opportunity.

That is what makes this conversation different. Maema isn't looking back on adversity after everything worked out. His story is still being written. He talks candidly about the uncertainty of life on the NFL bubble, the business behind roster decisions, the mental challenge of not knowing what comes next, and the mindset required to keep believing in yourself when there are no guarantees.

In this episode, Maema discusses:

• His journey from Stevenson High School to Wisconsin and the NFL
• Becoming a Wisconsin captain - and then fighting to stay on the field
• Why he remained loyal to Wisconsin rather than entering the transfer portal
• What mattered to him when choosing an NFL agent
• Going undrafted and why he “never looked at the odds”
• Beating those odds to make Cincinnati's 53-man roster
• Being released by Cincinnati and getting another opportunity with Carolina
• How quickly circumstances can change for players living on the NFL roster bubble
• Why “what seems like rejection is really just redirection”
• Handling the pressure, uncertainty and ambiguity of an NFL career
• What it means to have a Warrior Mindset

At one point, Maema describes his current life as a free agent as a “war of attrition.” Whether the next call comes tomorrow or five weeks from now, his focus remains the same: get his body better, keep his mind calm and sharp, stay in shape and be ready when the opportunity comes.

And when asked what it means to be a warrior, Maema explains that one of the biggest battles in professional football isn't physical. It's mental - dealing with pressure, uncertainty, ambiguity and adversity and continuing to move forward.

His message extends far beyond football:

“What do you do? How do you respond?”

LIFE ON THE NFL BUBBLE is a rare look at professional football from the perspective of a player whose story is still being written—and at the hundreds of players fighting every year for another opportunity to play the game.

🎙️ 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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Negotiation Warriors, Episode #016 - THE CBA NEGOTIATOR with Jeff Pash

For more than four decades, Jeff Pash helped shape the business and labor framework of the National Football League.

As the NFL’s Executive Vice President and General Counsel, Pash served as one of Commissioner Roger Goodell’s closest advisors and played a leadership role in some of the most consequential negotiations in professional sports—including two landmark collective bargaining agreements governing more than $100 billion in league revenues and player compensation.

Those agreements helped establish the foundation for what could ultimately become 20 years of NFL labor peace, during a period of extraordinary growth in league revenues, player salaries and benefits.

It is rare to have an interview with Jeff Pash. In this special episode of Negotiation Warriors, he takes us inside the preparation, strategy and decision-making behind negotiations at the highest level of professional sports.

In this episode, Jeff discusses:

• His remarkable 40-year career in professional sports
• Building consensus among 32 NFL clubs
• Why the CBA is critical to the NFL’s success
• Preparing four years in advance for the 2011 CBA
• The keys to nearly 20 years of NFL labor peace
• Negotiating the NFL’s rookie compensation system
• Why great opponents can make you a better negotiator
• How listening and compromise lead to better outcomes
• Why the NFL preferred face-to-face negotiations
• Staying calm and respectful under pressure
• Lessons from the NFL for college athletics
• Why great negotiators keep ego out of the deal

Throughout the conversation, Pash provides a rare look behind the scenes at negotiations involving billions of dollars, 32 NFL clubs, thousands of players and the future of the game.

And when asked what he believes is one of the most important lessons for any negotiator, his answer is remarkably simple:

“It’s not about you.”

🎙️ 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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What separates good negotiators from great ones?

Agent Rick Smith believes it isn't about winning every negotiation—it's about building relationships that last decades.

In Episode #015 of Negotiation Warriors, Cliff Stein sits down with one of the most respected negotiators in professional sports. As President of Priority Sports and a veteran agent with more than 25 years of experience representing NFL players, coaches, and executives, Rick has negotiated some of the most significant coaching and executive contracts in football while earning a reputation for honesty, trust, and integrity.

Throughout the conversation, Rick shares the philosophy that has defined his career:

• Why relationships are the foundation of every successful negotiation
• How to understand the other side's objectives before discussing numbers
• Why emotional intelligence often matters more than leverage
• The danger of backing someone into an intellectual corner
• How transparency builds long-term credibility
• Why great negotiators are problem solvers—not adversaries
• Lessons from negotiating NFL coaching and executive contracts
• The challenges facing today's rapidly changing college athletics landscape
• Managing leverage when you have it—and when you don't
• Building a legacy based on trust, humility, and respect

One of the most memorable moments comes near the end of the interview when Cliff describes Rick as someone who simply "tells it like it is." Rick doesn't hesitate.

"You're going to know right away. Unbelievably transparent. Unbelievably honest."

Whether you're an attorney, sports agent, executive, coach, student, or business professional, this episode is filled with practical lessons on leadership, negotiation, communication, and building relationships that create long-term success.

If you enjoy this episode, please Like, Subscribe, and Share. New conversations with the greatest negotiators in professional sports are released regularly.

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🎙️ Negotiation Warriors – Episode #014: THE CALM WARRIOR:
Megha Parekh on Leadership, Resilience & the Strength to Be Vulnerable

For years, I have admired Megha Parekh for one quality more than any other. Calm.

No matter how complex the negotiation…

No matter how high the stakes…

No matter how much uncertainty surrounded an issue…

Megha always seemed to approach every challenge with remarkable composure.

Then one sentence revealed the strength behind that calm.

"You don't have to be so tough."

Those six words, spoken by former Jaguars General Manager Trent Baalke the morning after Megha survived a terrifying home invasion, became one of the defining moments of her career. Rather than hiding her struggle, she chose something far more courageous.

She chose vulnerability.

In Episode #014 of Negotiation Warriors, I sit down with one of the NFL's most respected executives to explore the leadership principles that have shaped her remarkable career.

Megha is the Executive Vice President and Chief Legal Officer of the Jacksonville Jaguars. During her thirteen years with the organization, she has helped guide complex legal matters, major business initiatives, stadium redevelopment, organizational strategy, and some of the most important decisions facing an NFL franchise.

But this conversation isn't just about football.

It's about resilience.

It's about emotional intelligence.

It's about empathy.

It's about preparation.

It's about discovering that true strength isn't pretending everything is okay.

It's learning how to manage life's most difficult moments.

IN THIS EPISODE, YOU'LL LEARN:

• How sports and music shaped Megha's journey from Harvard Law School to the executive offices of the Jacksonville Jaguars.

• Why some of the greatest mentors don't simply open doors - they help you see potential in yourself before you can see it.

• The leadership philosophy that transformed her from "the no fun police" into one of the NFL's most trusted executives.

• How a terrifying home invasion forever changed her perspective on leadership, vulnerability, and resilience.

• Why Trent Baalke's simple words—"You don't have to be so tough."- became one of the most important lessons of her career.

• Why "managing it is the source of strength" may be one of the most important leadership lessons every executive needs to hear.

• How becoming a certified crisis counselor transformed the way she negotiates, listens, and leads.

• Why empathy is one of the most underrated skills in every negotiation.

• The surprising connection between heavy metal, Bon Jovi, playlists, breathing, and performing under pressure.

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🎙️ Negotiation Warriors – Episode #013

YOU DON'T KNOW ME

THE NEGOTIATION WARRIOR MINDSET OF KELLI MASTERS

At her very first NFL Combine, one of the most prominent NFL agents in the industry looked Kelli Masters in the eye and told her:

"You don't belong here."

Her response would become the defining mindset of her remarkable career as a successful sports agent: "You don't know me."

In Episode #013 of Negotiation Warriors, I sit down with one of the true pioneers in professional sports representation.

Kelli is the founder and president of KMM Sports and has represented more NFL players than any woman in the industry. In 2010, she became the first female agent to represent a Top 5 NFL Draft pick, breaking barriers and helping pave the way for future generations of women in sports.

But this conversation isn't just about football.

It's about resilience.

It's about purpose.

It's about leadership.

It's about refusing to let someone else define what you're capable of accomplishing.

Throughout our conversation, Kelli shares the lessons she's learned over more than two decades representing NFL players, building meaningful relationships, overcoming adversity, and negotiating with integrity in one of the most competitive businesses in professional sports.

IN THIS EPISODE, YOU'LL LEARN:

• How a conversation with a player's mother changed the direction of Kelli's career.

• Why purpose—not money—became the driving force behind her success.

• The unforgettable story of being told she didn't belong in the NFL agent business—and how one courageous response changed everything.

• Why persistence is one of the most important qualities for success in sports, business, and life.

• How kindness, respect, and relationship-building can become powerful negotiation strategies.

• Why preparation remains the greatest competitive advantage in every negotiation.

• The negotiation behind Blake Jarwin's $24.25 million contract and the lessons learned from standing firm.

• How representing Gerald McCoy, the No. 3 overall pick in the 2010 NFL Draft, helped launch her career.

• The biggest mistakes she's made as a leader—and how adversity became her greatest teacher.

• Why trusting your instincts and maintaining your values matter more than ever in high-pressure negotiations.

• How NIL has transformed athlete representation and why Kelli believes it has created new opportunities for agents committed to serving athletes with integrity.

• The leadership philosophy behind her book, High Impact Life, and why success should be measured by impact—not titles or contracts.

Kelli also shares her thoughts on mentorship, leadership, overcoming self-doubt, balancing priorities, and why the best negotiators don't have to be the loudest people in the room.

Whether you're an executive, attorney, coach, agent, entrepreneur, student, or someone striving to become the best version of yourself, this episode offers timeless lessons on resilience, leadership, negotiation, and living a life of purpose.

Sometimes the most powerful response to criticism isn't anger.

It's quiet confidence.

"You don't know me."

🎧 Listen now: Search Negotiation Warriors wherever you get your podcasts.

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