But the NFL superagent - said by some (especially himself) to be the real-life Jerry Maguire - lost it all. Now, two years sober and emerging from bankruptcy, he's trying to get back in the game.
FORTUNE -- The most famous words in the history of sports representation are fictional, sure. But Leigh Steinberg, the man famed as the original superagent, still claims responsibility for their provenance.
It was the spring of 1993, the week of the annual NFL owners' meetings in Palm Desert, Calif. Steinberg, whose clientele included future Hall of Famers such as quarterbacks Steve Young and Troy Aikman, had arranged for filmmaker Cameron Crowe to spend time with one of his clients, safety Tim McDonald. Crowe was researching a movie script about a charismatic sports agent; McDonald was trying to charm his way out of free-agent limbo and into a new jersey.
One evening, with CNN's Moneyline playing on the television in the athlete's room at the Marriott, the director listened to McDonald vent about the off-season: the travel, the glad-handing, the stress. Then, depending on whom you believe, McDonald said either, "Someone's going to have to show me some money" (that's the player's memory), or, as Crowe recalls it, "Where's the money? I've worked so hard. I can't do this forever. Where's the money?"
Of course, the exact quote that inspired the director is beside the point. Once the words were shouted on screen by both an exasperated athlete (Cuba Gooding Jr.) and his agent (Tom Cruise), they proved iconic for all involved. Steinberg was already an A-lister in the sports world: Every year he threw the biggest Super Bowl party and signed the biggest prospects. More than anyone, he had feasted as athlete contracts surged from five figures to seven. But Jerry Maguire meant cultural immortality. Ever since the premiere in 1996, Steinberg swears, he hasn't gone a single day without someone yelling "Show me the money!" at him, whether he's walking around an NFL stadium or his local 7-Eleven. Plenty of others have heard him yell it too.
But 16 years later, on a recent evening in Newport Beach, Calif., the world's most famous sports agent shuffles into a drab Urgent Care center, and there is only silence. At age 63, Steinberg -- for years hailed as the real-life Maguire -- now finds himself a bankrupt, recovering alcoholic, plotting a comeback from the bottom. And before 10 p.m. tonight, as mandated by the California Bar Association, he must show that his urine is clean.
When Steinberg appears in front of his new Irvine offices on a sundrenched afternoon, he grins and spreads his arms wide, joking, "Welcome to our luxurious digs!" Self-deprecation is his preferred approach to his station -- he's standing by a dumpster in a parking lot -- but it only lasts so long. Wearing white sneakers, jeans, and a long-sleeve polo shirt that, on inspection, is inside-out, Steinberg walks down a dim hall and reminisces about how his old memorabilia-laden practice, on Newport Beach's Fashion Island, doubled as "a museum where people would just come and stare."
Today, if those same people could locate Steinberg Sports & Entertainment, they would stare for a different reason. SSE is currently just a DBA ("doing business as"), not yet an official company. Steinberg occupies a small office with Tom Van Voorst, a fellow recovering alcoholic and lawyer who is also his roommate. The two met at a Sober Living facility in 2010 and now share an apartment in Laguna Niguel. Van Voorst runs errands in Steinberg's maroon Mercury Mountaineer and fields phone calls. "I don't pay him," Steinberg says, "but he gets use of the car, which you'd be totally screwed in Southern California without. And he does the cooking!"
Their condo, like the new office, has been a dramatic adjustment. A visit doesn't reveal much in the way of personal possessions -- it came furnished -- save for an artsy menorah Steinberg has set on the mantel. The agent's Chapter 7 bankruptcy filing from Jan. 11 accentuates the point. Asked to list his assets, Steinberg could produce only the car ($6,700), a Vizio flat-screen TV ($1,000), miscellaneous personal effects ($650), and a Wells Fargo checking account containing $100. That isn't much to go on for Richard Marshack, attorney for the bankruptcy trustee, whose mandate is to find potential assets and redistribute the money to Steinberg's long list of creditors, which include the Irvine Co. ($1.4 million in rent on his old office space); San Diego Private Bank (a $400,000 loan); his younger brother, Don (a $7,500 loan); and a dentist ($7,000 in fees). Sixteen creditors are listed, combining for $3.2 million in total debt. The bankruptcy proceedings should wipe the slate clean -- with the exception, possibly, of one claim that could crush Steinberg's professional revival.
An ex-client, NFL special-teamer Chad Morton, alleges that Steinberg owes him as much as $858,851, plus interest. In 2003 a Steinberg employee took a $300,000 loan from Morton, allegedly to fund a business venture in China that failed. Steinberg, who says he didn't know about the loan when it was made, agreed in 2008 to pay a settlement of $900,000. ("I didn't get into this business to do harm to athletes," he says.) He hasn't been able to come up with the money. Morton's lawyers say they plan to file a complaint alleging that Steinberg engaged in fraud, breach of fiduciary duty, or willful malicious misconduct -- any of which would make his debt to Morton non-dischargeable, even after filing Chapter 7.
It's a clear violation of NFLPA rules for an agent to solicit a loan from a client. Steinberg, facing discipline, let his certification to represent players lapse in 2007. He retains a handful of non-NFL clients -- Italian filmmakers Antony and Fulvio Sestito and Southern Methodist University football coach June Jones -- but pro football is his game. In January he reapplied for NFLPA certification; the players association won't say when it will issue a decision.
"I can do the NBA, I can do baseball," says Steinberg. "Why I haven't quite yet is that I've been under the Damocles sword of litigation."
At his desk, bare except for two Dr Pepper cans and a Sharpie, Steinberg mentions another loss that gnaws at him. A couple of years ago San Diego Private Bank had the idea to raid two storage lockers that contained Steinberg's sports memorabilia, and sold much of it off. He swears that if the bank had waited -- Steinberg says he was in rehab at the time -- and conducted an auction with his help, it could have made far more than it did. "I had hundreds and hundreds of helmets and footballs and trophies," he says. "Pictures of me with four or five Presidents! All that stuff."
On display around him are the few items the bank did not grab: a photo of him and Ted Kennedy; an autographed Steve Young Sports Illustrated cover; and a few items dating back to 1975, when his very first client, quarterback Steve Bartkowski, was the first of his unprecedented eight players to be chosen No. 1 in the NFL draft.
In the late '60s and early '70s, when Leigh William Steinberg was an undergrad and then law student at the University of California at Berkeley, there was little glamour and less money in athlete representation. Many in the business found the very term "agent" demeaning -- they insisted on calling themselves attorneys.
Back then, Steinberg had seemed destined for entertainment or politics. High-cheekboned and slim, the type-A son of a high school principal (father) and librarian (mother), he'd been elected student council president at every stop from Marina del Rey Junior High to Berkeley Law. But of all the famous men he encountered on Berkeley's campus -- from Jimi Hendrix to Ronald Reagan -- the most valuable connection he made was to the school's future football star: the 6-foot 4-inch, rocket-armed Bartkowski.
As a 1L, Steinberg worked as a counselor in Bartkowski's freshman dorm. He stayed close as the quarterback lifted the Golden Bears from mediocrity. "Leigh turned up at every party we were at," recalls Bartkowski's college girlfriend, Lori Forthmann. Finally, when Bartkowski was a senior in 1975, the quarterback became Steinberg's first client.
For both men the dividends were immediate and life-altering. That year Atlanta had the first overall draft pick. Steinberg, just out of law school, negotiated the richest rookie deal in NFL history: $650,000 over four years with the Falcons, better than the $400,000 that the Jets had given Joe Namath in 1965. Upon touching down in Atlanta the night before the signing, Bartkowski and his baby-faced attorney were met by klieg lights and a mob of fans; the local NBC affiliate cut into Johnny Carson to broadcast an airport interview. Steinberg likes to say that after gazing out his airplane window, he looked at Bartkowski "the way Dorothy looked at Toto when they entered Munchkinland."
Sure enough, the economics of giant TV contracts and free agency would soon propel pro football into fantasyland. Steinberg quickly became perhaps the best recruiter of his day. His talent wasn't discovering diamonds in the rough -- rather, he sought out obvious top prospects and, through charisma and bargaining skill, got them piles of money. He negotiated Steve Young's record $42 million rookie deal with the (now-defunct) USFL's Los Angeles Express in '84. Five years later he did both Warren Moon's $10 million contract with Houston and Troy Aikman's $11.2 million rookie deal with Dallas. ("I thought, 'This is the smartest guy I've ever been around,' " Aikman recalls.) And the commissions -- typically 4% to 5% for contracts and 15% for endorsement deals -- rolled in.
By 1985, Steinberg was no longer working alone. That year he married his college sweetheart, Lucy, with whom he would have two sons and a daughter, and partnered with agent Jeff Moorad. But to many he remained a solo act. For decades Steinberg hosted and carefully choreographed over-the-top Super Bowl parties, so-called conventions of Americana where politicians (say, Harry Reid or Gabrielle Giffords) mingled with musicians ('N Sync, Outkast) who shook hands with businessmen (Rupert Murdoch, Bob Kraft) and celebrities (George Clooney, Jay Leno). At his apex, in 1999, Steinberg represented a staggering 86 NFL players.
For all his wealth, Steinberg tended to go barefoot and eschew Rolexes. He maintained an earnest, boyish playfulness, once bursting into Bears finance director Ted Phillips' office with a client, rookie quarterback Jim Harbaugh, and unloading a water gun on the executive. Steinberg mailed books to his players and urged them to get involved with charities and public service. "Leigh was saying, 'I am a good, trustworthy guy,' " says lineman Ken Ruettgers, a former client. "And he was also saying, 'Oh, by the way, let me show you the numbers: We also get top dollar.' It was brilliant, and he separated himself from the herd."
So much so that when Crowe went looking for guides to Steinberg's booming industry in the early '90s, he gladly took the superagent's invitation to shadow him for a year. In exchange Steinberg received a fee, a cameo, and a creative consultant credit -- he coached the cast and hung around the set -- as well as untold amounts of publicity. What no one anticipated was that just as the movie was released in 1996, the man who portrayed himself as the real-life Maguire was quietly beginning to fall apart.
He had always been a person of extremes. Aikman, who says he watched Steinberg's weight and drinking habits fluctuate severely, knew that well. A September 1996 arrest in Newport Beach for drunken driving -- Steinberg pleaded guilty and was given probation -- was the first thread to unravel. In 1999 the agent, along with Moorad and a third partner, David Dunn, sold the firm to Assante Corp. for $120 million. Two years later, in an acrimonious split, Dunn left and took several dozen clients with him, leading to a lawsuit and a settlement for Steinberg, Moorad, and Assante. In 2004, Steinberg lost his father, Warren, his biggest influence. The next year he lost his mansion in Newport Beach because of mold. The next brought Morton's lawsuit and the start of his troubles with the NFLPA. And the year after that, Steinberg lost a second home when, also due to mold, the roof caved in from rain.
Baffling investments didn't help matters. Among Steinberg's many failed businesses were a Dallas restaurant, a radio network, and at least five Internet startups. "I had the right vision," Steinberg says. "We were just 10 years ahead." At his five-hour-long debtor's hearing last February, the recitation of his ill-fated web stocks grew so lengthy that lawyers cracked jokes at Steinberg's expense.
In April 2007 the agent who used to remind clients, "If you're going to drink, don't drive," did both in Newport Beach once again, crashing his Mercedes ML 500 into three parked cars and a fire hydrant around 1 a.m. (Steinberg pleaded guilty to misdemeanor charges.) At upscale parties his drink of choice had been Grey Goose; steadily, though, he lowered his vodka standards from Blue Ice to Smirnoff to, finally, "when I ran out of money," hefty plastic jugs of Popov.
By the end of 2008, Steinberg and his wife had divorced. He had blacked out, he says, after drinking in front of Steve Young's family on the night the 49ers retired the quarterback's jersey. And he had been arrested for public intoxication after he was found shouting and trying to scale a hill near the Newport Auto Center one night at 7:45 p.m. (He pleaded guilty.) Most troubling to him, Steinberg mangled his relationships with his daughter, Katie, and two sons, Jon and Matt. The sons have both been diagnosed with retinitis pigmentosa, a rare progressive eye disorder that causes blindness. His kids were often on the receiving end, Steinberg sadly admits, of harsh "drunk-calling and drunk-texting."
Today Steinberg 's primary employer is the law school at the University of California at Irvine. He teaches sports law, a gig that arose after an enterprising 2L from England, Paddy Browne, contacted him via Facebook. The dean set up a three-hour lecture course on Thursday afternoons. ("When I got the news," Browne recalls, "I remember thinking, 'This must be like how Leigh feels when he signs a big client!' ") Steinberg, toting his battered pigskin briefcase (a "good luck charm," he says), shows up at class on the seventh Thursday in jeans and an untucked button-down shirt, stained at the collar with tobacco juice. Dipping is a vice Steinberg returned to during alcohol rehab, to which he finally committed himself in March 2010. Seated on a stool at the front of the room, spitting into an empty soda can, he begins by saying, "Tuesday, I spent five hours in a bankruptcy hearing. Brother, can you spare a dime?" The joke falls flat.
After the students file out, Steinberg thumbs through his BlackBerry. In spite of his tumble to the bottom, he receives daily requests to jump into business -- with Internet startups, with nutrition companies, with a production outfit that wants to make sports movies. "I can take a concept, figure out how to uniquely brand it, and drive it to market," he says confidently. He's also mulling an offer to do a reality show, finishing up a guide for parents on how to raise athletic children, and writing his memoir. (Steinberg's first book, written with Michael D'Orso and published in 1998, was titled Winning With Integrity: Getting What You're Worth Without Selling Your Soul.) "Because of my Forrest Gump-y life and all the hotness right now, it could be really big," he says.
It is not clear whether the bankruptcy trustee -- whose attorney, Marshack, praises Steinberg for being "very, very cooperative" -- would have any claim to all that hotness. But they are looking into whether money made from Steinberg's life story would be theirs to take. Under California bankruptcy law, Steinberg was relieved to learn in February, he is free to work, and any income he reaps from a new client or deal is his to keep. Any money still coming to him from clients or deals that began before filing for bankruptcy is the trustee's.
Of all his possible ventures, the most contested may well be the avenue Steinberg insists is his top priority: a grand return to athlete representation. As he waits to hear about NFLPA recertification, his ex-colleagues and competitors wonder whether the industry he and Jerry Maguire helped inflate -- there were over a thousand registered NFL agents by 2005 -- has passed him by. Agents look on, agog, as a noted alcoholic prepares to plunge back into a business still laced with drink. "An individual with an addiction needs to understand this illness is life-threatening and a disease that is not willed away," warns top baseball agent Scott Boras. "It is forever."
Steinberg has anticipated such concerns, particularly from the parents of prospects. He has sound bites -- rehearsed but emotionally genuine -- at the ready. "Our world is a Disneyland of drinking," Steinberg says. "I think it's an asset to have someone who's been through these behavioral problems and understands what effect alcohol has."
His BlackBerry, after class, shows no fewer than 15 new e-mails about athlete representation. The senders range from a weightlifter to the mother of a college swimmer. "I wonder if you might consider representing my son," one parent writes. "He's a freshman in college, and he's a pretty good athlete!"
Steinberg smiles. "I don't think so," he replies aloud, politely. He says that unlike with vodka, he won't be plumbing the bargain bin of clients simply to ease into the game again. No, he'll be gunning for the mega-prospects befitting a superagent.
Exiting the waiting room at Newport Urgent Care, having just handed in the plastic cup, Steinberg chalks up another good day. Sober since March 21, 2010, he says, "I'm not struggling with temptation anymore." But he's also realistic. In the morning, after waking, he tells himself only, "There's a great probability I won't drink today."
When Steinberg began Alcoholics Anonymous, he says, "it was nonstop meetings, nonstop conventions and dinners. I didn't know which part of it would necessarily work, so I did every single thing there was to do. I was a little bit type A about it." In the past three years he's also done stints in Sober Living and has "worked the program," handwriting letters to clients -- including Young, Moon, and Aikman -- that Steinberg felt he'd embarrassed. "Part of what happens," he says, "is the fog lifts."
Each morning he calls in to the California Bar's Lawyer Assistance Program to find out if he must provide a random urine sample. He works out at the gym with a personal trainer. He fields e-mails from prospects and phone calls from well-wishers like Charles Barkley. He meets for scheduled dinners with his children. He gives "about a speech a week" at schools or businesses. He says it felt odd, on the Saturday before this past Super Bowl, to be home and not throwing a party. Instead he posted five dispatches on his blog, including one about his daughter urging him to read The Hunger Games.
Not that Steinberg can ever escape his previous self. Or Crowe's movie. Once, he says, at an AA meeting, he went to the bathroom and encountered someone who asked him to autograph a Jerry Maguire VHS. It was awkward, obviously, but Steinberg loves telling these stories. Like the one about taking Cuba Gooding Jr. to the Super Bowl, pretending he was a client, to prep him for his role in the movie. ("I told him, 'If you do this well enough, you might even get an Oscar nomination,' " Steinberg says; of course, Gooding did win, for best supporting actor.) Or the day Crowe asked him to evaluate the throwing arm of actor Jerry O'Connell, who played quarterback Frank Cushman, Maguire's top client. ("I had to show him how to throw a football!") A favorite photo shows Steinberg with his arms around Gooding and Cruise, both of whom point a brotherly finger at the man wedged between them. A cropped version appears on each page of Steinberg's website.
But in the movie about the man behind a football star, was Steinberg really the man behind the character? There are doubters. Cruise, who declined to comment, told HBO in 2002, "He is not Jerry Maguire … But he did like to keep going on in that way. It got to the point where it was a little ridiculous." Crowe consulted with several prominent agents for the movie, including the late Gary Wichard and Drew Rosenhaus -- who also had a cameo as himself and has claimed to have inspired the title role. But the filmmaker speaks fondly of Steinberg and confirms that his contribution was crucial: "Leigh helped enormously with access and the details with which we could fill in the character." Crowe's crew took photographs of Steinberg's office and used some of his mementos on the set.
Steinberg, presented with these complications, pauses, then begins to chuckle. Yes, he admits, there were big differences between himself and Jerry Maguire. The fictional agent was a small-time, odds-defying rebel; Steinberg had started out with a No. 1 draft pick and swiftly rose to the top of his field. Even so, Steinberg reaches into his bag of memories and pulls out another one from the making of the movie, a story Crowe confirms. The director had a catch phrase he would use to describe his protagonist, words that now comfort Steinberg as he plots his own sequel: "Jerry Maguire aspires to be you."
This article appears in the April 30, 2012 issue of Fortune and the April 16, 2012 issue of Sports Illustrated.
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