FORTUNE — He’s back — maybe.
The man who director Cameron Crowe shadowed for a year as research for the movie Jerry Maguire has a new book out and has initiated a return to athlete representation. Leigh Steinberg, the subject of a 2012 Fortune/Sports Illustrated feature profile (See: “They showed him the money”), was recertified by the NFLPA in October after being unable to represent football players since 2007.
The superagent, who represented star quarterbacks like Steve Young and Troy Aikman, struggled with alcoholism in the mid 2000s and in 2012 filed for bankruptcy, losing $3.2 million. Now he is nearly four years sober. He has reopened his business, Steinberg Sports and Entertainment. He has ambitious plans. Whether he will succeed is uncertain — at 64 it may be hard for him to compete with young agents for rookie clients — but Steinberg remains honest about himself and his mistakes. He’s also one of the most experienced, knowledgeable sports fans around.
Steinberg stopped by the Fortune offices on Wednesday for a talk that was often funny and sometimes surprising. What follows is an edited transcript.
FORTUNE: So you’ve been recertified in football.
Leigh Steinberg: I got recertified, and I’m certified in basketball. With baseball, you get certified when you get a client. In November, I found a group of businessmen in Houston to fund me to build out the same kind of business I tried to do before, which is to aggregate talent in baseball, football, basketball, hockey, mixed martial arts, all the sports. That would trigger a large marketing arm that could market teams, leagues, conferences, individuals, and corporations. We’d also have a studio that would do sports-themed motion pictures, television, and video games.
That’s a tall order. It sounds like a CAA-sized organization.
Yes, well. The representation piece is just one part. The business of sports representation is not remunerative for anybody who’s not at the top. The fee cap in football is 3%, and now the salaries are so standardized and capped that to be honest, I couldn’t walk into a room and tell a football player’s parent that I have a magnificent ability to change the first contract.
Now, you’re only talking about rookies, right, because the stars get big signing bonuses that do vary in value.
Yes, that’s where the money went. All that makes sense now is stars. We’re also setting up a foundation called Athletes Speak, which will position them, for the first time, to speak out about concussions. One of the problems has always been the denial of older players and how stoic they are. No one talks about it.
Football head injuries have always been an important issue to you.
I’m so desperate for a solution. I call it a ticking time bomb. I believe [the head-injury crisis] poses an existential threat to football, because mothers will tell their children, “Play any sport but football.” That won’t kill football. The socioeconomics of those who play it will change. It’s one thing to know that from playing football you will have pain in your hip and knee, and lack of mobility, and when you go to pick up your child it will be painful. It’s another thing not to be able to identify your child.
The first task is changing the culture of youth football so you don’t have kids tackling with the crown of your head. The second thing is a helmet that actually helps. Currently the helmet only prevents skull fracture, it doesn’t help with concussion. So I’ve found and am helping this company Tate Technology, founded by Jenny Morgan who is the granddaughter of [John Tate Riddell, the founder of] Riddell. They are working on a helmet that, through compression, dissipates and attenuates the energy flow, and in tests, one category showed 46% less impact.
How are you useful to a company that’s making a helmet?
Because of my brand in the field and access to officials in sport, I can publicize it, and I can get it funded and delivered. You see, that helmet will not only affect football, it affects baseball, hockey, even bicycle and motorcycle helmets. This is a massive worldwide issue; football just happens to be the straw that stirs the drink.
Your brand is what you’ll have to use to drive your new business, too.
Yes, we can work with charities, and we can help certain companies and projects. We can help populate them with athletes. You want to bundle services together and give clients one-stop shopping. But the real play is owning the next new television show or the technologies I’m talking about.
I’m going to be a producer on a movie called Born in June, about June Jones [coach of SMU]. Kevin Costner might play the lead. It’s like what I did with Jerry Maguire — you get a big open. You’re running on the sports section as well as the entertainment section. So, television packaging: I agreed to host a show that’s not sold yet — but I’m not producing it — called So You Want to be a Superagent.
Especially with Jay Z now running a sports agency, I imagine a reality show about wannabe agents would do well.
He has been very shrewd. He understands what I said about the pyramid, so he has targeted very elite players.
Right. Robinson Cano, Kevin Durant, Victor Cruz. But also Geno Smith.
That contract [Smith’s] was criticized. And Cano had to go to Seattle … where you’re surrounded by the ocean, Canada, wheat fields, and Portland, Oregon.
Do you think other agents are annoyed about Jay Z, or they welcome him?
I think his use of [baseball superagent Scott] Boras’s name in a lyric [“Scott Boras, you over, baby” on the song “Crown”] was frightening and struck some terror. And that goes into the popular consciousness now. But I think he will have a great appeal, especially to people from his own background. He will be able to say, “I came out of this broken background, I transcended that and became a business success.” Right now he is offering a unique opportunity to come in on the ground floor. He is able to say, “You will have my personal attention.” But athletes are fickle and can get jealous of each other. Later on [as his agency gets bigger], he will have the same problem other agents do. To the extent that he keeps his business elite the way he has, I think he will be successful.
Speaking of building athletes into a brand, what did you think about Richard Sherman’s comments after the NFC Championship game?
To me this was the functional equivalent of Miley Cyrus twerking. This was his twerking moment. He has the best sense of time and place, in terms of self and branding, of any athlete I’ve seen since Deion Sanders.
So is this a guy you’d want to represent?
Well, you would have to sit down with him and see what he’s really like. He’s obviously not like that 24/7. My thing is, Would you be a role model? I think as a marketing strategy, the Super Bowl is still the premiere marketing event in America. It’s the largest brand-building opportunity, and if he plays well in the game itself, he can become a household name.
Cornerbacks don’t usually become household names the way a quarterback does.
Shutdown corner is one of the four most important positions in football. But it’s much more subtle; it’s an obscure position. If you asked fans at a stadium to name a corner, I’d be surprised if more than 20% could do it. That’s why I represented starting quarterbacks in my prime, because they were the leading men.
So then, was what Richard Sherman did smart?
If his goal was to raise his profile and brand himself in a certain way, then it was. In America, you can always soften out imagery — bad boys become better boys. But what’s really hard to do is get through the Tower of Babel of competing media to ever carve a niche. So I think it was brilliant, from a marketing standpoint.
Have you signed any clients yet with the new business?
No. Not yet, because we were so late — we started in November and people had already recruited clients for next year. We’re only eight weeks into the whole deal. But I am throwing my big Super Bowl party this year [after not having one for the last two years].
Who will you root for?