No. 190: LEIGH STEINBERG / He wanted them to show him the money ... again. The rise and very hard fall of the agent who shaped the economics of the NFL.
I went to Newport Beach with expectations that the agent for a slew of Hall of Famers would have a lavish layout, Lifestyle of the Rich & Famous ... y'know, that sort of thing. Not remotely close.
The NFL draft is coming up in a few weeks and the projected first-overall pick, USC quarterback Caleb Williams, will be in attendance with friends and family and no agent. Williams has made news lately with his decision to go without an agent and negotiate his own contract. Shudder. That has worked out well for some, not so much for others.
I’ve written feature profiles of folks on the business side of sports over the years and none gave me richer material to work with than Leigh Steinberg, who back in the day represented nine No. 1 picks and a slew of players who’d go on to the Pro Football Hall of Fame. He wasn’t a celebrity agent … he was the celebrity agent. He even had his own trading card.
To re-iterate, I said, “back in the day,” because when I spoke to him ten years ago he had fallen farther and harder than anyone I had ever profiled and was trying to mount a comeback. I didn’t include Leigh Steinberg in How to Succeed in Sportswriting (without Really Trying), the Audible Original that gave this SubStack its name. A slip on my part. If I do a “physical” book version of my memoir, I’m going to work in a chapter on Steinberg. Below, find the story that I wrote for Sportsnet which had me visit him in Newport Beach, California. The working title was SHOW ME THE MONEY. With hand-written scrawl that appeared in the opening spread I amended the title. SHOW ME WHERE THE MONEY WENT. And yes, that’s my handwriting that they used in the display.
I loved the funky layout of the piece, other jottings, coffee cup stains and various other effects. Unfortunately the piece isn’t available anywhere online. A month after my story appeared, the New York Times Magazine also profiled Steinberg. The Times went with SHOW ME THE MONEY (AGAIN). I like my title better … and my story of course. You be the judge. Do check out the postscript—it’s a killer you’ll never see coming. You’ll understanding why I have all kinds of time for Leigh Steinberg and I’m not alone.
ONE: HOW TO THROW A SUPER BOWL PARTY
Represent dozens of the highest-paid players in the NFL. Have hundreds of famous friends, including franchise owners and Hollywood stars. Don’t dwell on the commissioner not sending you an invitation to the league’s official Super Bowl party. Use your party as the ultimate slap-back for the snub. Start by inviting 350 fabulous friends to your plush crib. Once your party becomes an annual fixture, book the ritziest venues in the host cities. Pose with the big names and land on Page Six. Repeat 25 times. Repeat once more and not just for good old days.
Snow threatened to make February’s Super Bowl at MetLife Stadium an embarrassment for the NFL. Nonetheless, the prospect of a whiteout wasn’t slowing down business. The Super Bowl belonged in New York, the crucible of commerce, where the power brokers on Madison Avenue were cutting $4-million cheques for a 30-second ad, where online bidding was driving up the price of a choice ticket as high as $449,645, and where, for the 26th time, Leigh Steinberg was staging a party to celebrate the occasion of the greatest of American games.
The New York Post made it out to the glitzy rooftop club at 230 Fifth. So did Forbes. Reporters took attendance. Steve Young, check. Kevin Costner, check. Serena Williams, check. Coverage would duly note the host’s thumbnail bio: that he has negotiated $3-billion in contracts over the past four decades; that he has represented eight No. 1 overall picks in the NFL draft; that his client list has included Super Bowl stars like Troy Aikman, Ben Roethlisberger and the aforementioned Young. A celebrity auction raised money for the Lone Survivor Fund, the veterans’ charity, and West Point cadets in full dress mingled with marquee names.
When guests paid their respects to Steinberg, they asked how business was going and he rhapsodized about this crewcut kid, Garrett Gilbert, standing wide-eyed and disbelieving beside him. Remember that name. With a Diet Coke in his hand, Steinberg surveyed the scene. OK, it’s not like the good old days when 3,000, even 4,000 made it out. Let’s just say it’s more intimate. Still, he smiled. This was how his comeback should look, like he never was gone.
TWO: HOW TO MAKE YOUR LIFE A FILM
Get a box-office star. Cast him as a decent man. Put him in a tough situation. Have him triumph against the odds. Remember that the facts always have to give way to a good story.
The most famous stories in business begin as case studies of inventions but ultimately evolve into the sagas of the inventors themselves. Creative genius begets an idea and then the visionary tells a tale that turns him into an icon. Thus the light bulb became Thomas Edison’s story, just as the production line became Henry Ford’s and personal computing Steve Jobs’s. Dust their legends and you’ll find their fingerprints all over them.
Not Leigh Steinberg. Someone else did the dirty work and made him into an icon. In fact, the story was so movingly written that it wound up nominated for an Oscar for Best Original Screenplay in 1996. It comes up whenever Steinberg’s story is told: Jerry Maguire.1 As Steinberg has said many times, more presciently than he imagined: “Once Tom Cruise has played you on the screen, life can only go downhill.”
Tom Cruise has to be wearing lifts in this shot.
Where Jerry Maguire ranks in the canon of sports films is open for debate. It did win Cuba Gooding Jr. an Oscar for chewing up the scenery as Arizona Cardinals wideout Rod Tidwell, imploring the title character, his agent, to “SHOW ME THE MONEY.” It also earned $150 million at the box office after its release in 1996. Steinberg’s contribution: The film’s writer-director, Cameron Crowe, shadowed him for a couple of years to get the backroom detail that lends the film its ring of truth. And Maguire owned a relentless common decency that mirrored Steinberg’s public image and ran counter to the stereotypes of the trade.
“Every day somebody will come up to me and say ‘Show me the money,’” says Steinberg, who awaits Guinness’s recognition for the lifetime record for forced smiles. However fatiguing that might be, he never shied away from his association with the film—there it is on the end of his Twitter profile: #RealJerryMaguire.
The lead character might have a bit of Steinberg in him but the plot of Jerry Maguire played out nothing like the agent’s life story. Maguire was a young hotshot turfed out of a major agency and wound up with a single journeyman pro on his client list. When Crowe followed Steinberg, he was the NFL’s alpha agent. He told reporters that he no longer needed to recruit players, that his phone was ringing off the hook, that he only had to pick which stars he wanted to represent. Not imperious about it, mind you, but those were the facts back in the 90s.
Crowe never made a sequel to Jerry Maguire, leaving us to presume that Cruise and Renee (“You had me at ‘Hello.’”) Zellweger plunked down and lived happily ever after. If there ever will be Maguire Redux, and if it hews more closely to Steinberg’s life and times, look for a far darker story. Not a rom-com, something closer to The Lost Weekend.
THREE: HOW TO BREAK INTO THE BUSINESS
Connect with a rising star without coming on too strong. Recognize opportunity. Position valuable incoming talent at the point of greatest leverage. Stand in the background when your client is signing a record-breaking deal. Make sure they spell your name right.
Leigh Steinberg wasn’t born into show biz, but nonetheless his birth 65 years ago was duly noted in the Hollywood Reporter. The industry journal announced his arrival because his father was the manager of the Hillcrest Country Club and friend to many Jewish stars and moguls denied membership at lily-white Gentile 18-hole enclaves. Thus the grandson grew up around famous actors and comics like Jack Benny and Groucho Marx, at least when visiting the golf course, and had opportunities as a child actor. “To grow up in Southern California is to be fascinated by the entertainment industry,” Steinberg says. “Acting, directing, producing, all of these seemed like career goals to me.”
The Steinberg home, however, was devoid of glitz. His father was a high-school principal and chaired the city’s human-rights commission. His mother was a classics-loving librarian. Dinner-table conversations could pass for small talk in a philosophers’ circle. “No one had a bigger influence on my values than my father,” Steinberg says. “He told me, ‘Treasure relationships. Make a difference in the world. Make it a better place.”
By the time the younger Steinberg applied to the University of California’s law school, he was torn between career ambitions poles apart: either the entertainment business or politics. The arc of his life took an unexpected turn at Cal when he served as a freshman dorm counsellor and struck up a friendship with a kid named Steve Bartkowski, a football recruit.
Four years later, Bartkowski was a first-team All-American as a quarterback and was considered the top player eligible for the 1975 NFL draft. With the prospect of talking contract with the Atlanta Falcons, the owners of the No. 1 pick, Bartkowski approached Steinberg, who was wrapping up law school at Berkeley. “Until then I hadn’t thought about a sports-law practice and sports law [in the NFL] was in its early stages,” Steinberg says. “Most players just represented themselves. And at the time, if a GM took a position that he didn’t want to deal with an agent, he could just hang up the phone.”
The Falcons could have hung up the phone on Steinberg when he called on Bartkowski’s behalf, but they were motivated to lock up the quarterback. They weren’t even half-filling Atlanta Stadium. The Falcons needed an attraction and believed Bartkowski would create a buzz. Negotiations would have proceeded as usual if not for a wild card: the launch of the World Football League, a rival loop with modest ambitions of trumping the NFL and taking the game into European and Asian markets.
The WFL had fielded 12 ragtag teams for its inaugural season in 1974, a steady cascade of debacles: Players went AWOL; teams relocated in mid-season; and, in a sublime climax, the IRS threatened to shut down the WFL’s first championship game unless the league immediately paid back taxes out of the gate. Most NFL executives believed the WFL wouldn’t last beyond a second season—and it didn’t, Nonetheless, the Falcons couldn’t risk a PR disaster that would spill over if Bartkowski chose the semi-glorified barnstormers over Atlanta. He wound up signing with the Falcons for four years at $650,000 and thus did Steinberg, a 25-year-old who had never considered working in sports law, break into the business with the largest rookie contract in NFL history—while he was prepping to write his bar exam.
It was neither Bartkowski’s contract nor his subsequent Rookie of the Year Award that most impressed Steinberg, but rather something that others wouldn’t have given a second thought to: the Atlanta NBC affiliate breaking way from Johnny Carson and The Tonight Show to cover Bartkowski’s arrival in the city. “I could see what a hold a sports star had, the star worship,” Steinberg says. “I saw the opportunity that an athlete had to do good things and make a difference. After that I talked to Steve and he got involved and gave to the United Way. And that’s something I impressed on my clients, the idea of making a difference.”
This is a story Steinberg has told hundreds of times and it could pass for a bit in a routine, yet those who have known him since the 70s insist it rings true and truly shaped his career. “Leigh’s a sincere, idealist guy and always was,” San Francisco Examiner columnist Glenn Dickey says. “He was and still is interested in social causes, liberal, progressive, whatever you want to call it. He convinced clients to get involved with charities, good causes that they cared about. With Bartkowski it was the United Way and with others it was education or social programs or something else. It wasn’t PR. That was just Leigh.”
With Warren Moon in Canton. You can make a strong case that Moon owes his place in the HOF to Leigh Steinberg, who was the only agent who’d give him the time of day. That’s why he tapped his former agent to introduce him at his induction.
FOUR: HOW TO WIN OVER A CLIENT
Do not hard-sell. Listen before you talk. Remember, if the heart is empty, the mind doesn’t matter.
You’d imagine the sports representation biz is rife with hucksters and hustlers, talking fast and, when necessary, bribing young athletes into the fold—but that has never been how Leigh Steinberg presented himself to the media, to the public and, most importantly, to a prospective client. He has never seen the point of winning a client that he didn’t respect or one who didn’t respect him. He always believed that mutual respect would get them through tough times.
Steinberg has a special place for clients whose careers were fraught with trouble early on. He needs to be needed. A pair of his Pro Football Hall of Fame quarterbacks provide instructive examples.
While Steve Young is best remembered for leading the 49ers to Super Bowl titles, the start of his career was one misadventure after another. Everything seemed to be rosy for Young when, coming out of Brigham Young, he signed a $42-million contract in 1984, the largest in North American sports history.
Buy a couple of problems arose.
First, Steinberg’s star client possessed the oddest of quirks: He didn’t want the money. Not that he wanted out of the contract, wanted to play somewhere else, wanted some other consideration. No, the day after Young signed, he told Steinberg to give all the money back and make sure that he was paid a salary equal to his teammates’ average and a side amount that would let him get an apartment in L.A. and four new tires for his 1965 Olds convertible. “I had never made a dime playing, but more than that I never thought about making money from a game that I loved to play, as corny or crazy as that sounds,” Young says. “I just couldn’t handle the pressure that went with [the contract] and I went back to Utah and went into hiding. I was a nervous wreck.”
Steinberg stepped in and coaxed his client out of his socialist impulses and insecurities. “Steve was an intelligent young man who didn’t care about money,” Steinberg says. “The money in the contract didn’t make sense to him and he felt like he couldn’t take it in good conscience. I talked him through it.”
The second problem was one more easily foreseen. Young had signed with the Los Angeles Express of the USFL, an update if not an improvement on the late, unlamented WFL. Predictably, the exactor of failure came in: The Express owner was succumbing to the unbearable lightness of pocket and the league was collapsing. When Young’s payments were missed and the owner was mining lint in his pockets, the USFL’s commissioner’s office believed the league was not on the hook for the balance of the quarterback’s contract. Au contraire, Steinberg said, waving a contract with layer upon layer of ingeniously wrought legal protections against the Express’s and USFL’s demise. Steinberg says: “Unless life as we knew it came to an end on planet Earth, Steve was going to get paid what was owed to him.”
Though Young walked away from the wreckage with lifetime security, his problems on the field didn’t end there. “I was stuck playing back-up in Tampa Bay and I was ready to quit, but this time Leigh got there before I went back to Utah,” Young says. “He told me he believed in me and I believed him when he said he
Steinberg engineered a trade that landed his client in San Francisco, and ultimately, in the Pro Football Hall of Fame. “It’s fair to say Steve was a unique client in terms of both talent and challenges,” Steinberg says. “We were going to find our way to the best possible outcome, but it hinged on Steve never losing belief in himself and faith.”
By contrast, Warren Moon’s problem was an existential crisis: Despite his impressive performance in the 1978 Rose Bowl, the University of Washington quarterback passed right through the NFL draft. All he had were offers to try out if he were willing to play another position. African-Americans were seen as lacking the “intangibles” necessary to play QB in the league, a bit of institutional racism straight out of the 19th century.
Some agents would have advised Moon to chase short-term returns that come from walking on with an NFL team at receiver or tight end. Steinberg realized that wouldn’t end well. “As an agent you have to understand your client’s hopes and dreams, his fears and anxieties,” Steinberg says. “Everyone always thinks it’s money—it’s not. Warren was never going to be happy if he wasn’t a quarterback.”
Most agents would have looked at the short-term returns in the NFL and assumed Moon would never be more than a bit player. Many of those would have tested the waters with a few phone calls and quickly lost interest in representing Moon. Steinberg took an immediate liking to him and added the undrafted free agent to his client list alongside the No. 1 overall picks. “Beyond talent on the field, Warren had an incredible belief in himself and an iron will,” he says.
As a point of pride and with the hope of a fair shake, Moon went to the Edmonton Eskimos. Over six seasons he proved himself as the CFL’s best quarterback and belatedly established a market for his talents in the NFL. He wound up landing a contract with the Houston Oilers that made him the league’s highest-paid player, a $5.5-million deal, front-loaded with a $4.5-million signing bonus.
Moon got a late start in the NFL but stuck around until age 44, throwing 291 touchdown strikes and passing for almost 50,000 yards. And in 2006, Moon asked Steinberg, the only guy to stand beside him through thick and thin, to introduce him at his Hall of Fame induction ceremony. “No one in the game had a bigger impact on my career than Leigh,” Moon says. “No one gave me more support. The time of the induction was a tough time for Leigh. I knew about his troubles. It had been building for years, just so many issues that he just couldn’t manage it all. The stress he was under would break anyone. I was worried about him. I was worried about him just getting through the weekend. But he did.”
FIVE: HOW TO LOSE IT ALL
Think big—really big. Take on partners. Take on proteges. Believe that all people are inherently principled. Gain confidence in your ability to make things work out. Too late in the day, go to court. Be unlucky and be weak.
Over the course of a couple of decades in the business, Steinberg established himself as a heavyweight behind the scenes in the NFL and a photogenic celebrity in the bright lights, with his blond hair and wholesome good looks befitting his white knight’s image. Cosmopolitan named him the magazine’s Bachelor of the Year in 1983. He modelled menswear in a fashion spread in GQ. His wedding to his high-school sweetheart was featured on Lifestyles of the Rich and Famous. As his profile rose, his ambitions grew. He talked about running for governor of California, even President of the United States. Laugh if you will now, but if you can get millions out of a moribund football league you might be able to pull off universal health care and gun control.
Back in those heady times, Steinberg grew his practice. When the workload became too much in 1985 and he was looking to add major league ballplayers to his client list, Steinberg brought in Jeff Moored as a partner in the agency. For the balance of the 1980s and through the 90s, theirs was a seemingly perfect professional relationship, Steinberg focused on the NFL, Moored on the MLB. While they negotiated tirelessly for their clients, Steinberg says that they spent “not one second figuring out how to divide the big pie” that was the agency’s profits. Theirs was the ultimate good-faith relationship. “Earlier … than he merited, I gave Jeff a stair-step to a 50-50 deal,” Steinberg says.
Further expansion proved problematic and, ultimately, destructive. Other associates were brought aboard in the late 90s, most notably David Dunn, who rode shotgun to Steinberg on the NFL client list. In retrospect, Steinberg can see how the agency was starting to go off the rails at that point. “Factors are going to create dissension,” he says. “People’s desire for public recognition, for financial recognition, younger associates’ ambitions to chart their own path … all of that is in play. When it comes to recognition, everybody tends to feel under-recognized. It’s human nature. In point of fact, the vast majority of time they tend to overvalue their own contributions.”
By the end of the ‘90s, 30 people worked on the agency’s staff. Steinberg had prided himself on his ability to empathize with GMs and owners at the bargaining table, but he had no read of his own office and was oblivious to the level of dissension in the ranks.
At the time, major entertainment talent agencies and corporate interests were acquiring sports agencies like kids collecting baseball cards. Assante, a Winnipeg-based financial outfit, made an overture to Steinberg that he was initially skeptical aboutL an offer to buy the agency attached with a promise that he would stay on and conduct business just as he had for the past 25 years. When the offer reached $74-million, Steinberg signed off on the sale.
Today, playing Monday-morning quarterback, Steinberg doesn’t need to view the game film to see the read he missed. “I under-valued the autonomy I had,” he says.
Issue escalated from Day One. Dunn believed Assante had shorted him to the tune of $2.5-million in stock. On a black day in February 2001, not even two years after the sale to Assante, Dunn bolted the agency and took several disenchanted staff members with him. Worse, he took more than 50 of the 84 clients. And, rubbing salt on the wound four weeks later, Dunn negotiated a record-breaking 10-year, $103-million contract for New England quarterback Drew Bledsoe, a former Steinberg client. (Dunn and his associates did not respond to several interview requests over the course of weeks from Sportsnet.)
When Steinberg and Assante filed suit for breach of contract, a courtroom street fight ensued. Round one went to Assante and, nominally, Steinberg. A jury awarded the plaintiffs $44-million in damages. The ultimate Pyrrhic victory: The award was going to Assante and left Steinberg’s reputation in tatters. Staffers he had hired years before had taken the witness stand and recounted his over-the-top outburst in the office, drunken embarrassments at public events, Bledsoe even testified that his wedding had been disrupted by an inebriated Steinberg. For years, friends and associates had tried to talk him into going to rehab, but Steinberg claimed his drinking never affected his work. Those protests now rang hollow.
It got so bad that even Tom Cruise tried to distance himself from Steinberg. “He’s not Jerry Maguire,” Cruise said.
Steinberg’s trip downhill was only gathering speed. No matter what the verdict, clients weren’t coming back and Steinberg’s phone was no longer ringing off the hook with calls from first-rounders. A year later, Steinberg bought out Assante for $6-million and he and Moored left with what remained of what used to be the biggest agency in sports. Assante officials dismissed the deal as trivial, saying the operating costs of the sports practice exceeded what it was bringing in.
In March of 2005, citing errors in instructions to the jury, a judge threw out the verdict in the breach-of-contract suit against Dunn. Assante would settle out of court with Dunn’s agency, Athletes First. Days later, Moored announced that he was quitting the biz to become a partner and executive with the Arizona Diamondbacks.
And then, in 2007, what amounted to the death penalty for the agency: One of Steinberg’s remaining associates had borrowed $300,000 from a client, Chad Morton, and not repaid the journeyman fullback. Morton slapped the agency with a lawsuit and no amount of Steinberg’s personal charm could put out the fire. The NFLPA decertified Steinberg, the agent who had made its members billions of dollars.
It would soon get bleaker still. If Steinberg had undervalued his autonomy, he had overestimated his business acumen. He had invested millions in dot-coms that had gone bust and money he had thrown into dubious retail and service businesses might as well have been thrown in the fireplace.
Not surprisingly, Steinberg’s family life also disintegrated. The marriage that began on Lifestyles of the Rich and Famous landed in divorce court and gossip columns. When the assets were being divided, the family home couldn’t be moved because of black mold. At the same time, doctors diagnosed Steinberg’s two sons with retinitis pigmentosa, a degenerative eye disease that can lead to blindness.
What Steinberg hadn’t lost, he seemingly tried to destroy. He was drinking half a gallon of vodka a day, one plastic jug of Popov after another. He was busted for drunk driving after bouncing his Benz off three cars and a fire hydrant on the Pacific Coast Highway. After a conviction for public intoxication, he holed up in the basement of the home he had grown up in so he could drink without being seen. The home was his mother’s by then; his father, the one person who might have been able to ground him, had died of cancer a few years before.
Five trips to rehab and countless interventions didn’t work but finally on March 20, 2010m Steinberg brought his drinking to a dead halt. It ended with humiliation. His brother Jim tried to check him into a detox facility for the drunk and indigent and the staff turned him away, pronouncing him not drunk enough to gain entry. In a brief time he drained another bottle and returned to the facility only to find that the last bed had just been taken. The party was over, and when sober, he took stock of the wreckage around him. “I drank to forget,” he says. “There was a lot that I was trying to avoid. Bills that didn’t get paid. Business I should have taken care of.”
In January 2012, he fled for bankruptcy protection, claiming that he was $3.18-million in debt. Creditors included Morton ($450,000), Southern Methodist University coach June Jones ($90,000), a SoCal socialite ($150,000) and various tax authorities. He also owed $1.4-million for unpaid rent on his office lease.
In the end, Steinberg listed $483,500 in assets: $475,000 in stocks; an 11-year-old Mercury Mountaineer valued at $6,700; a $1,000 flat-screen TV, $150 in clothes (roughly the price of a single shirt he modelled in GQ) and $50 in personal memorabilia. At his five-hour debtor’s hearing, the recitation of his ill-fated dot-com stocks grew so lengthy that lawyers cracked jokes at his expense just to break up the monotony.
By rights, it should have all ended there.
It didn’t.
SIX: HOW TO SAVE YOUR LIFE
Listen to those who love you. Understand your addiction. Understand there are things to live for. Understand that there are loved ones to live for. Be prepared to try and fail and try again … and fail and try again and fail, etc, etc, etc.
The Super Bowl party on Fifth Avenue was supposed to be the rollout of Steinberg’s re-entry into the game, but even his favourite former client and one-time business partner remained skeptical about the prospects of success. “Leigh was at the summit but I don’t know if he can climb up the mountain,” Warren Moon says. “I don’t think his future is in agentry. He’s probably the most intelligent man I’ve ever met and he has so much to give in other ways.”
And Steinberg is giving back. He’s serving as an adjunct professor of law at Chapman University, a Christian school in Orange, California. He’s mentoring young grads who want to get into sports law.
He’s also looking for new business ventures, including the development of a reality-show, a sports-biz version of The Apprentice that will wage a contest to find the next super-agent. And he’s out telling his story. This spring he’s crossing the U.S. to promote The Agent. a memoir of his professional life and white-knuckle victory over alcoholism.
All this looks like the next stage for Steinberg as Moon envisions it. Still, Steinberg wants back in, not to make history, not to rebuke one-time friends and colleagues who ruined his good name, not because this up-at-dawn, pride-swallowing siege is all he knows. He understands better than anyone how the industry landscape has changed since he was driven out. His nemesis David Dunn is now the most powerful agent in football. The first-rounders go to Dunn and his Athletes First agency, 51 in the past five drafts. Dunn negotiated Green Bay quarterback Aaron Rodgers’s seven-year $130-million deal, the largest contract in league history. Steinberg knows he’s competing against a turbocharged version of his former self.
And it doesn’t matter. A place in the game would give him a chance to make a difference. Channelling his inner Jerry Maguire: A client completes him.
Once sober, Steinberg moved into an apartment with a lawyer who went through the 12-step program with him. He attended AA meetings in a Methodist church. He had to go for regular urine tests as laid out by the California bar association. He had to apply to be re-certified by the NFLPA, the same union that collected dues off the billions his clients made over the years.
These days you’ll find Leigh Steinberg’s office in a modest plaza he shares with a bus-tour company, a wine-boutique and a Kinko’s, a short walk from the place where he pinball his Mercedes off parked cars and a hydrant and blew into a breathalyzer in the back of a cruiser. Steinberg Sports and Entertainment takes up three adjoining rooms on the third floor, his office overlooking the water. Charitably, you’d describe the space as nondescript.
Steinberg is 65, a suitable age for a retirement he would have trouble affording. “I have friends who’ve retired, but it doesn’t interest me,” he says. “I love my work. It keeps me young.”
Well, somewhat. The ordeals that visited him or that he brought on himself have made him less boyish. Surgery for skin cancer left a fresh scar on his temple. He’s 30 lbs over his fighting weight, his gut rolling over his belt. Still, he owns a ridiculously thick and blond head of hair that would look appropriate on a high-schooler. And he wears the self-satisfied smile of a kid in the front row who just got the highest mark in the class.
A working day in April 2014: To keep relatively young, he’d make 100 phone calls over an 11-hour stretch in his office. He’d hold incoming calls during a lunch meeting with three businessmen from Houston who are bankrolling his practice. “I’ve always had good luck with Houston and Texas,” he says, after seeing them off. He drains another can of Diet Dr Pepper and loosens his belt. “I know lots of business people there. Ray Childress, one of my former clients there, is a partner in the Texans. Getting my clients involved in teams’ communities, developing relationships with owners, gave them a chance to meet businessmen who could help them after they retire from the game.
Steinberg wasn’t just looking to Texas for investors, but also for luck once more. He was going into the NFL draft just like he did in 1974: with one client. Quarterback Garrett Gilbert isn’t Steve Bartkowski and wasn’t going to be Steinberg’s ninth No. 1 pick. He had been USA Today’s high-school player of the year in 2008, but he struggled in college, first at the University of Texas and then at SMU. By the spring of 2014 he was all Steinberg had. Then again, he might have been the most important plater in Steinberg’s professional career.
Draft insiders had Gilbert ranked well outside the top 10 senior quarterbacks and declared underclassmen. The NFL didn’t bother inviting him to the combine, the league’s seal of approval for prospects. ESPN had Gilbert ranked 315th overall, which would leave his name outside the 256 who were going to be called over the three days of the draft in May. Still, after the Super Bowl party in New York, Steinberg brought Gilbert to San Diego to work with a quarterback coach to prepare for private workouts.
After he saw his Houston backers off, Steinberg called his client and he was transported back, not to bygone glories but to the previous weekend: the occasion of Gilbert’s pro day, his workout on a high-school field for NFL scouts. Steinberg had watched his clients work out for NFL scouts in hundreds of sessions before. “Maybe with the exception of [the 1990 No. 1 overall pick] Jeff George, Garrett’s was the best I’ve seen,” he says.
Before he flew out of Dallas, Steinberg had sent a text to Gilbert reiterating his appraisal of the showcase: “TERRIFIC!!!!” Since then, on the hour, he was keeping his young client apprised of every glowing review he heard about through the grapevine. “I think Leigh might be more excited about it than I am,” Gilbert says.
Some in the trade didn’t regard Steinberg’s landing this kid as a recruiting coup. After all, his father is Gayle Gilbert, a back-up quarterback for Buffalo back in the 90s and a former Steinberg client. Still, Garrett Gilbert says family history wasn’t the only reason he selected Steinberg. “My coach at SMU is June Jones and he really respects Leigh,,” he says. “They go way back.”
If Steinberg can use a creditor named in a bankruptcy filing as a professional reference, then no one should rule out a comeback that would be the stuff of Hollywood.
This and other ironies seemed lost on Steinberg.. He sat at his desk and stared absently out onto the harbour. High on the bookshelves behind his desk and looking down down on him were foot-high cardboard cutouts of Thurman Thomas, Bruce Smith and Troy Aikman among others, like residents of a thought bubble left over from 1992. “I’ve done this for 40 years,” Steinberg says. “Garrett is going to get drafted. It just takes one person to like you.”
SEVEN: HOW TO START OVER
Understand that victory is a qualified and temporary condition. Understand that defeat is not the end if you don’y surrender.
Leigh Steinberg sits in the living room of Gayle Gilbert’s home in Austin. He has gone over it with father and son. Before the draft began, he drew up a list of team that were going to be in the market for a quarterback and had expressed an interest in young Garrett. Now, midway through day three of the draft, hitting the sixth round, the second-last of the nerve-eroding ordeal, the list of possibilities has dwindled to just a couple of teams with other more highly regarded throwers still on the board.
Steinberg has sat in hundreds of living rooms over his three decades in the trade. It was where it always started, the setting for recruiting a client, He has sat in humbled homes of dozens of kids who grew up in poverty. He sat in a few sprawling mansions where young men had grown up accustomed to all the advantages. But this is draft day, and draft day always meant New York, where the big names walked on stage for their gridiron graduation day.
In Jerry Maguire, the story reaches its payoff at the Super Bowl. So Hollywood. No, that’s not where the story of this agent—down to one lonely client—would end. This gut-wrenching siege must end unseen and unshared. A living room in Austin without. camera in sight: that seems fair.
On the television screen: “With the 214th pick, the St Louis Rams selected Garrett Gilbert, quarterback, SMU.”
The commentators call up a thumbnail profile on their computer screens and remind viewers that the Steelers are on the clock.
In Austin, an old agent and a young man who were both on the clock are smiling and crying.
“You made it happen,” Gilbert says to his agent.
“You made it happen for me,” Steinberg tells him.
They know all of it hasn’t happened yet. A contract remains and Steinberg will handle the paperwork, but there won’t be any negotiation. A sixth-rounder won’t be looking at guarantees and bonuses, just a contract around the league minimum that the Rams can vaporize if Gilbert struggles in training camp. And even if he makes it onto the roster, Gilbert would be the No. 3 option, like his father had been.
Knowing what there is still to do, and the long odds against glory, they keep the celebration muted. Years ago, Steinberg and his first-overall pick celebrated in style, in awful excess. Back to the presidential suite or ballroom rented for the occasion, reporters chasing them for interviews. Not now, though. Leigh Steinberg can only stay a couple of hours. He has a flight to catch to LAX, where it will begin again. Day after day, he’ll stand on the sidelines at practices and workouts, sit in dozens of living rooms listening to and reassuring prospects and parents, and spend thousands of hours on the phone, This is what must go into the production of a sequel so melancholy and relentlessly hopeful that the floor of the next Super Bowl party will be carpeted with wet hankies.
Postscript: At age 74, Steinberg is still out there stroking. He’s still working out of the same office in Newport Beach. For a year ago, here’s a Sports Business Journal photo of him standing down by the harbour his office overlooks.
From Spotrac.com: In the 2023 season, Steinberg had three NFL clients, two journeymen making around $1-million and New Orleans running back Jamaal Williams, who earned $3-million last season. So, sorta Rod Tidwell. Worth noting: Patrick Mahomes has brought in Steinberg to work with him, though to this point, the agent has yet to represent him in contract talks … so there is that. The sportsbusinessjournal.com profile linked here is the most up-to-date look at Steinberg’s life and times—there’s no die in him whatsoever.
Here’s video from his latest Super Bowl party. Vegas seems to suit him.
And, oh yeah, the single client that Steinberg was representing when I talked to him. The Rams cut Garrett Gilbert before the 2014 season, but he landed a third-string role with the New England Patriots, who went on to beat Seattle in Super Bowl XLIX. Didn’t get in the game, of course, but still came away with a Super Bowl ring, what his dad had four cracks at with Buffalo. He would bounce around to several teams for nine seasons, last drawing a NFL paycheque in 2022. Career numbers: 75 passing attempts, one touchdown, one interception, a QB rating of 75.2. No less than Warren Moon does Garrett Gilbert owe his good fortune to Steinberg’s belief in him.
One strange personal connection to Jerry Maguire. My good friend, actor Donal Logue, played one of Maguire’s tormentors at the agency the protagonist was fired from. He’s the red-hair laughing jackal next to the odious and untalented Jay Mohr.