Leigh Steinberg was one of the most highly touted sports agents. (Saul Gonzalez/Only A Game)

Leigh Steinberg was a star sports agents before his life took a turn. (Saul Gonzalez/Only A Game)

The movie “Jerry Maguire” features Tom Cruise playing a fictional hot-shot sports agent. His character is based on real-life sports agent Leigh Steinberg.  Although Steinberg was once the prince of sports representation, he had a fall from grace and now, at age 64, he’s staging a comeback.

The Height Of His Career

“I don’t think a day’s gone by since 1998 where someone hasn’t said, ‘Can you say show me the money?’ or they say, ‘Show me the money,’ ” Leigh Steinberg said. “The fact that it’s happened 10,000 times before, it still shows that people are interested.”

“It would be hard for someone in [sports] to not know what I’ve been through because it’s been so public.”
– Leigh Steinberg,
on being open about his addiction

At the height of his career in the 1980s and ’90s, lots of people were interested in Steinberg, especially a who’s-who of professional athletes who sought out his representation in high stakes negotiations with team management and corporate sponsors.

Steinberg, who started as an agent right after graduating from the UC Berkeley School of Law in the ’70s, became especially known for representing the NFL’s top players.

“Back in the day, it was Ken O’Brien and Tony Eason, and Kenny Easley and then Troy Aikman, Steve Young, Warren Moon, Ben Roethlisberger,” Steinberg said. “I would go to games, and in one Super Bowl, all six quarterbacks in the game, both sides, were my clients.”

Steinberg represented the No. 1 pick in the NFL draft a record eight times.

“His is one of the fascinating stories,” said Ken Shropshire, who teaches sports law at the Wharton School of Business and is the co-author of the book “The Business of Sports Agents.” “He certainly is one of the most successful people in the business over the years.”

Shropshire says Steinberg got clients and attention because he was very different from so many other sports agents of the time: boyish, clean-cut and with a reputation for honesty.

“He was around in the days when you had agents who were successful because they had fur coats and Rolls-Royces, and they were pretty brazenly paying athletes to allow them to represent them,” Shropshire said. “That was not the space that Leigh traveled in.”

Leigh Steinberg speaks at a 1996 press conference with client Sugar Ray Leonard. (Todd Warshaw/Getty Images)

Leigh Steinberg speaks at a 1996 press conference with client Sugar Ray Leonard. (Todd Warshaw/Getty Images)

Steinberg says professional athletes liked him because, beyond making them lots of money in contracts, he could see beyond their machismo.

“It’s sitting down with him in a quiet way, peeling back the layers of the onions, so that he will finally show his greatest hopes and dreams and biggest fears and anxieties,” Steinberg said. “Men don’t share easily. It’s understanding that person not generically as a player, but who he is. “

For decades things went very, very well for Steinberg, with the sports agent reportedly negotiating $2 billion worth of contract deals for his clients. 

And then this sports business golden boy had a very long and hard fall.  

The Hard Fall From The Top

“My father died a long, lingering death of cancer, and he was really the rock in my life,” Steinberg said. “My two kids were diagnosed with incurable eye disease. We lost a home due to flooding and had to demolish it. And ultimately I got a divorce. And I felt at at that point like my world had come apart. I felt like Gulliver on the beach, tethered down and Lilliputians sticking forks into me.”

He turned to the vodka bottle for comfort, becoming an alcoholic and getting arrested for DUI and public drunkenness in 2007 and 2008.

Steinberg, through a series of bad business deals, also lost his sports agency and agent’s license, which he partially blames on the booze.

“I didn’t lose clients over alcohol,” he said. “I just walked away from it. I was still highly productive at work, but there were not as many days of work.”

Starting Over

Now after more than 1,400 days of being clean and sober, Steinberg is trying to rebuild his life and reclaim his place in the sports business pantheon.

Steinberg’s got his agent’s license back. He has a new sports agency backed by investors from Texas. And he has projects ranging from a new autobiography to plans for a television reality show. When he’s not talking to the media, Steinberg is talking to potential clients, trying to convince them that he’s banished his demons and can represent them effectively.

“I am completely open and transparent about what happened to me and how I reacted to it. Absolutely,” he said. “These are close relationships. Now, it would be hard for someone in the sports area to not know what I’ve been through because it’s been so public.”

The athlete representation business, though, has changed during Steinberg’s years-long absence from the scene, with giant talent agencies, like CAA and IMG controlling more and more of the market and athletes packaged more and more like pop stars. However, Steinberg is not intimidated about diving back in because, he says, he has little left to lose.

“At 64, I’m starting over again at a point where a lot of my friends are retiring,” he said. “But I really don’t cherish the concept of gardening in the backyard. I’ve had four years off. Four years of stored energy, excitement, vision. And the projects are flooding in here.”

We don’t know how much business Steinberg is really juggling, but he has signed people like former Southern Methodist University quarterback Garrett Gilbert as a new client.

As he attempts to bounce back, Steinberg says he’s once again ready for people to — well, you know the line.