Leigh Steinberg: The Real Story Behind The Sports Empire

Leigh Steinberg, premier sports agent, entrepreneur, best-selling author, and Chairman of Leigh Steinberg Sports and Entertainment Holdings, is best known for his work building athletes into stand-alone brands. He is often credited as the real-life inspiration for the Oscar-winning film Jerry Maguire.

Leigh has represented many of the most successful athletes and coaches in football, basketball, baseball, hockey, boxing, and golf, including the number one overall pick in the NFL draft for an unprecedented eight times in conjunction with 64 total first round picks. With an unrivaled history of record-setting contracts, Leigh has secured over $4 billion for his 300+ pro athlete clients and directed more than $800 million to various charities around the world.

This Episode’s Heavy-hitter’s:

Leigh learned “everything he needed to know” about negotiating from his time serving as President of the Student Government at UC Berkeley, where he frequently had to meet with then Governor Ronald Reagan. The two would later laugh about those days, but at the time when the Vietnam War was dividing the sentiments of the people, things were tenser.

Another lesson Leigh learned was from Tom Cruise. During the time Leigh got to meet Tom while he was acting as Jerry Maguire, Leigh saw that Tom has a “complex life.” He was able to put in context for his players that you have a choice when things are getting complex– to double down and persevere or to crumble.

During his bout with Alcoholism, Leigh focused on the basics when getting clean. He made a promise to himself that no matter what else happened, as long as he got clean and took care of his family, he would be happy.

The greatest enemy of athletes, according to Leigh, is self-absorption. So Leigh works to develop athletes and helps them to network and put in the work to help and influence others.

One major approach Leigh thinks is necessary to successfully promote DEI is to get more minority personnel into organizations at younger, entry-level positions.

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