It’s Only a Successful Negotiation if Both Parties Win, According to Leigh Steinberg
By Chris Benguhe, RaeAnne Marsh and Elaine Pofeldt | May 29, 2025 12:03 pm
Representing pro sports players isn’t a zero-sum game for the renowned sports agent.
“If you can put yourself in another person’s heart and mind and see the world the way they see it from their goals and their perspectives, you can navigate your way gracefully through life.” That sentence sums up Leigh Steinberg’s approach to his career and the world beyond it.
If you’re a sports fan, you know of Leigh’s prowess in negotiating contracts for pro players in football, baseball and basketball. Having represented 12 pro football Hall of Famers, he has negotiated more than $3 billion in contracts. He is widely credited as the inspiration for Tom Cruise’s character in Jerry Maguire, who made the line “Show me the money” famous.
He also created the Leigh Steinberg Foundation For Concussion, Traumatic Injury and Brain Health. The foundation reflects his concern for the many players who suffered lifelong implications from brain injuries sustained on the field, and their families. “My dad used to say, ‘Look, when you’re looking for someone to make a difference in the world, solve a problem,’” he said. “‘As small as picking up a piece of trash, as big as racism, and you keep waiting for the they and them to solve the problem — older people, political figures, they’ll take care of it.’ He would say, ‘You could wait forever. The they is you, son. You are the they.’”
Leigh is a big believer in the importance of character among sports players and has long encouraged them to use their platforms to inspire their communities and have a positive impact.
He has urged them to set up scholarship funds, do charitable work and tackle social issues through their foundations. His belief? By treating clients holistically and considering their long-term well-being, he can help them achieve both professional and personal success — one that lasts long after they’ve retired. It’s one he shares with those entering the field at a two-day agent academy he started.
“Every time you agree to represent someone, you’re carving out a little bit of your own life and there’s a finite amount,” he said. “So, you want to be careful. I need to have an ethical, moral underpinning to the work I do in the world to feel good about it. So, you want to feel great about that client and the impact he’ll make.”
He shared this and more when he spoke recently with Chris Benguhe, founder and president of the Dave Alexander Center for Social Capital. Click on the link below for their conversation.