It’s a different time now, but the world is still filled with judges, and on this springtime Thursday, Smith is pacing outside a private room at the Beverly Hilton. It’s the site of the NFL Players Association’s annual Rookie Premiere, a gathering of the top 40 draft picks, and on the other side of a sliding door are some of the sport’s most powerful agents, a group deeply divided about Smith’s performance as the NFLPA’s executive director.
“A strong leader,” super-agent Drew Rosenhaus says afterward.
“A joke,” another agent will say, speaking on the condition of anonymity out of concern for retaliation by the union.
A former trial lawyer, Smith has led the NFLPA, the world’s most robust professional sports union but the one also most likely to chew off its own tail, since 2009. He’s best known as a prominent face of the 2011 lockout, the longest in league history, and as the NFL commissioner’s adversary-in-chief.
“I know Roger Goodell wanted to be here tonight,” Smith joked to the crowd at the union’s 60th anniversary gala in 2016. “However, lying, cheating and stealing is a full-time job.”
A savage and unnecessary attack, perhaps, at the NFL commissioner — or maybe Smith needling his counterpart, the leader of an organization he sometimes calls a “cartel,” is precisely part of his job. And that’s the thing about Smith: Most everything about him and his job performance over the past decade can be credibly debated — and often is.
On one hand, he oversaw the end of the lockout and the resulting collective bargaining agreement, an important piece of sports legislation that led to key advances in player health and safety along with the fairest revenue split ever between NFL owners and players. But was Smith, who had virtually no experience in sports or labor law before taking the country’s most high-profile job in sports labor — two years before ratifying a document that guaranteed management would receive 53 percent of revenue over the next decade — fleeced by the league’s billionaire owners?
“He’s very sound. He knows the game. He understands economics. He’s very intelligent,” says one of those owners, the New England Patriots’ Robert Kraft, whose team has — according to Forbes — nearly tripled in value since the signing of that CBA. “I like him a lot.”
The NFL has indisputably been the country’s richest and most influential sports league for decades. But though players run the ball and make the tackles, owners’ leverage has never been seriously threatened. Strikes have failed, contracts remain non-guaranteed, and though players have been willing to stand up to what has become a corporate leviathan — from the failed strike in 1987 to an awkward player response to Colin Kaepernick’s protests three years ago — there’s no doubt who holds the power.
Which leads to another debate about Smith: Is he a blustering rabble-rouser leading an unwinnable charge, or is his refusal to cede any ground, his reluctance to peacefully coexist with his adversaries, to evade conflict — even, occasionally, against the 2,000 men he represents — precisely what the union needs at a time when players’ voices are stronger than ever?
“I just remember thinking, like, ‘You don’t have to fight everybody,’ ” said a former member of the NFLPA’s executive committee, the 11 current and retired players who help steer the union’s direction and work closest with Smith. “ ‘You don’t have to fight us.’ ”
On this day at Rookie Premiere, Smith sits at the head of the table and launches into an opening statement. There’s a war coming in 2021 between players and league owners, he warns, probably another work stoppage, and that means the temporary drying of a bountiful cash cow. He insists the agents must convince their clients, whose salaries average about $3 million but whose careers generally span about three seasons, to start savings accounts “no later than tomorrow” in advance of a strike or lockout.
A hand goes up, and an agent asks why they’re even discussing this. It’s two years away, and everyone in the NFL has it better than ever. Shouldn’t the focus be on peace, not conflict? If Goodell were to call tomorrow and offer to extend the current CBA, the agent asks, wouldn’t Smith accept?
“F--- no,” he says without hesitation. “Now, that’s just me.”
'Wired to be combative'
Not long after he was elected in March 2009, Smith met Goodell at a brasserie in Washington, D.C. The dinner was cordial enough, Smith would recall, but at the end, Goodell slid across the table a lapel pin in the shape of the NFL’s red, white and blue shield. A decade later, Smith, 55, sees the gesture, ostensibly a welcome to the league, as condescending.
“I’m kind of wired to be combative,” Smith will admit, and following the meal he did what he does: He ruminated, fortified his defenses, vowed to never be taken advantage of.
His first act was to order a now weathered copy of “Political Prisoners in America,” a 1973 book written by Charles Goodell, Roger’s father and a former U.S. senator who lost his career and reputation because he had spoken publicly against the Vietnam War, defying his political party and the wishes of President Richard Nixon.
Smith studied the memoir as a handbook for the NFL commissioner’s influences and motivations, the ideas and fallout that shaped him, and over the years he would highlight passages and revisit certain pages. For a while, he carried the book to Upshaw Place, the NFLPA’s headquarters near Dupont Circle in Washington. Smith’s predecessor, Gene Upshaw, had been a Hall of Fame offensive lineman who then ran the union for 25 years before dying of pancreatic cancer in August 2008. For better or worse, Upshaw had run the NFLPA like a family business; more important, he had presided over two decades of labor peace with former NFL commissioner Paul Tagliabue, a former attorney who had cross-examined Upshaw during the Oakland Raiders’ antitrust lawsuit in the early 1980s.
In the early part of Upshaw’s tenure, the NFL was a trade organization run by millionaires — not a corporate titan whose roughly $15 billion in annual revenue would put it in the top half of the Fortune 500. This was before mammoth television contracts or stadiums that cost billions or even player free agency. Back then, an NFL executive is famously quoted as having told Upshaw that the league was the ranch and players were “cattle,” an ultimately replaceable asset.
And indeed, when there was a player uprising, it was usually a disaster; the 1987 strike ended after 24 days, and multiple stars crossed the picket line. So maybe it was natural that Upshaw and Tagliabue, recognizing the league was on the verge of staggering growth, agreed it was better to go along and get along.
“War is pointless,” Tagliabue says he and Upshaw decided, though the men nonetheless faced accusations — from either side — of being too cozy. “We had to build something together.”
Then Tagliabue retired in 2006, replaced by Goodell, an NFL lifer who had been groomed for decades to become commissioner and the league’s unilateral authority figure. When Upshaw died two years later, a search firm scrambled to find a few outside-the-box candidates who might stand up to the commissioner.
At the time Smith was a partner and corporate lawyer at Patton Boggs, a powerful Washington law and lobbying firm, with ties to Barack Obama and his attorney general Eric H. Holder. Smith recalls engaging with the search firm but assuming he had no chance because the entirety of his football experience was playing cornerback at his Maryland high school. But eventually that outsider status placed him among four finalists gathering in Hawaii to make final pitches.
Smith had compiled a 300-page manifesto he would call a “war plan,” and he told players they needed a leader unafraid of conflict. A great battle was on the horizon, he would tell them, and as an attorney he didn’t avoid taking a case to trial; he relished it, arguing about 150 cases before a jury. Smith closed with an impassioned plea: Players must take NFL owners seriously about their threats of a lockout, the first since 1970.
“You need to have a guy who doesn’t bluff,” Smith would recall saying, and though some voters remained unsure how to correctly pronounce their new leader’s name — it’s duh-MORE-iss, though usually he goes by “De” — he was the right man for the time.
Almost immediately, Smith’s talks with Goodell were strained. Tensions became further inflamed in 2010, when the league office hired former union president Troy Vincent, Upshaw’s right-hand man and considered by many to be his likely successor. Smith still considers the move out of bounds for the NFL and views Vincent as a turncoat. Over the following decade, interactions between Smith and Goodell would become a microcosm of American politics: declarations to reach across the aisle ultimately giving way to gridlock and base loyalty.
Smith suggests Goodell, despite his reputation, actually possesses little real influence on the league’s agenda. Calling the commissioner, Smith says, usually leads to Goodell reaching out to a key franchise owner — often Kraft or Dallas Cowboys owner Jerry Jones — so if Smith now wants to resolve something, he might spend 20 minutes talking with Goodell and three hours directly lobbying an owner. An NFL spokesman declined to make Goodell or Vincent available for an interview.
Smith, though, insists he nonetheless respects Goodell as an opponent and that their relationship has, as he puts it, “evolved.”
But does he trust him?
“He and they are formidable,” he says after a long pause. “I mean, they’re like Russia, right? They’re like old Russia. You can control the machinery of industry and at the same time have absolute control over the press that I would argue no other business in America has. So they’re formidable, and they’re dangerous.”
Questioned by agents, players
As Smith settled in, he found himself constantly under attack, and the most serious threats often came from inside his own building.
With Smith in charge, the NFLPA hired a half-dozen attorneys from Washington law and consulting firms, instituted biannual performance reviews and required departing employees to sign nondisclosure agreements.
“That’s the way a business is run,” Smith says, suggesting the union under Upshaw had a reputation for being too “clubby.”
Smith occasionally struck some as aloof or defensive, in particular when it came to his inexperience in football — “He came in ready to be disrespected, ready to be offended,” one former executive committee member says — and critics’ opinions escalated following the 2011 lockout. Smith had correctly predicted the work stoppage, and even now he suggests the experience was valuable for players: a painful lesson in how far owners are willing to go.
But perception of what players gained in the CBA has aged poorly. One influential NFL agent suggests, nearly a decade after the deal was ratified, that Smith was such a ham-handed negotiator that when he sat down at the bargaining table, owners were willing to offer players 55 percent of total gross revenue. When the agreement was finalized, players received just 47 percent.
According to offer sheets and other documents made available by the NFLPA, that total revenue, which is what players had access to before 2011, isn’t the same as all revenue, which represents their cut now. The 2006 labor agreement, Upshaw’s last and a deal now seen as unusually generous to players, allowed owners to take considerable deductions before players could access their share. Those exemptions totaled about $500 million; five years later, they had grown to $1.1 billion. The current CBA merged those items, eliminated the deductions and gave players a minimum 47 percent of all revenue over the life of the deal — a smaller slice of a considerably larger pie. The new pact also mandated the league overall to spend at least 95 percent of the salary cap (individual teams must spend 89 percent of their budgets) over four years, reduced hitting in practices and improved post-retirement benefits.
Regardless, many agents and players, including former San Francisco 49ers offensive lineman Alex Boone, were convinced Smith had blown it. Owners, appearing to celebrate a landmark win, spiked Goodell’s annual compensation from roughly $11 million in 2010 to a combined $108 million over the first three years of the new CBA.
It didn’t help that Smith — in the most blue collar of American sports — can come across as a hyper-academic Beltway creature, refusing to simplify his language even when explaining advanced economics.
“A lot of guys were pissed about it, and here’s this fast-talking lawyer from D.C., and I thought: ‘This f---ing guy, he’s all over the place,’ ” Boone says now. “I’ve been in rooms with De where guys have gone after him, like really tried to cut him open.”
The divide between the union and agents, who tend to be players’ primary messengers, only widened. The new CBA shifted bigger-money contracts toward veteran players and away from unproven rookies, largely eradicating incentive-based negotiations and hefty commissions for agents’ most expensive clients. Appearing to twist the knife in 2015, the NFLPA proposed stricter certification requirements for agents; a year later, the union’s board of player representatives installed a provision that could cut agents’ standard fees from 3 percent to 1.5 percent.
“He got his ass kicked so bad in the last negotiation,” another agent says, “that the only way to deflect attention is to create diversion.”
After running unopposed for a second three-year term in 2012, Smith had become so polarizing by 2015 that eight finalists — among them a retired Navy rear admiral, two lawyers and a pair of former NFLPA employees during Smith’s first years — were on the ballot to unseat him.
“A referendum on the leadership,” says Jason Belser, a former NFL player who gave up his 11-year union career in part to challenge his boss. “I wanted to leave and end my tenure at the players association with my reputation and credibility. Because it was eroding every year.”
Kennedy, Churchill, Batman
A few years ago, Smith reported to Upshaw Place and learned there had been a fire in his private restroom. But hadn’t his office been locked? Even now, Smith wonders whether one of his colleagues broke in and tried, quite literally, to smoke him out.
“We laugh now,” he says, though he actually doesn’t, and when he’s asked a moment later how long ago he stopped suspecting his co-workers from trying to kneecap him, he replies, “What’s today?”
Some colleagues roll their eyes, and others figure this is just De being De. He’s likable, funny, passionate — but the man overflows with bravado, and his job in fact calls for a certain ability not just to tell stories but to sell players on topics and their urgency: brain injuries, the damaging effects of the painkiller Toradol, a work stoppage that might never happen.
“You have to tell them why they should care,” says Eric Winston, who spent a dozen years as an NFL player and is now the NFLPA’s president. “Apathy will kill us.”
And so, no matter the audience or forum, Smith tells his stories. Here’s one: He was one of four African American kids at Riverdale Baptist School in Prince George’s County when a teammate started jawing in the locker room about a girl they both liked. What had been a tense situation escalated, he says, and after a racial slur was hurled, well, all Smith remembers is trying to slam his teammate’s head into the concrete floor. They eventually made peace, he says, and decades later Smith suggests he could have — maybe even should have — let it go. But he didn’t, and here’s the story’s climax: When Smith meets with the NFL commissioner, that teammate and their fight spring to mind.
“My first Goodell,” Smith will say, and it’s hard to know whether he actually means this or it’s another attempt at painting the NFL commissioner as a players’ antagonist.
Regardless, Smith has never been much good at letting things go. His parents, his mother a nurse and his father a former sharecropper and the great-grandson of a slave, taught their two children to challenge authority and be steadfast. During one of a half dozen interviews for this story, Smith compares himself with John F. Kennedy, Winston Churchill and Batman — principled figures who persisted despite enemies.
Not long ago, Smith was sitting at the bar of an airport Chili’s when a man approached. He didn’t like that Smith and the NFLPA publicly support Kaepernick and other players who protest racial inequality during the national anthem. The union’s charge is to back all players — from those accused of domestic abuse to those who prefer their footballs underinflated — but rather than explain that or just ignore the man, Smith soon found himself hurling expletives and slinging insults at a total stranger.
“Is that an example of maybe being chippy? Maybe,” he says. “But you know, underneath all that there’s a slight tinge of racism right beneath the surface, right?”
Of all the debates about Smith, he often has one with himself: Does he have to be this way? Every day? On everything?
As much as Smith seems to thrive in conflict, he prefers movies with happy endings and has spent decades trying to be more like James Baldwin, the iconic writer and civil rights activist. Baldwin, Smith believes, burned just as hot and cared just as much. But look how cool he was, so in control of his emotions despite that underlying fury, and before important meetings with key NFL owners or player representatives, Smith studies video of Baldwin’s 1965 debate with William F. Buckley Jr., the conservative author and commentator and founder of National Review.
“The flag to which you have pledged allegiance along with everybody else,” Baldwin says in his opening, “has not pledged allegiance to you.”
Smith loves it, has probably watched the black-and-white footage three dozen times, but invariably the inspiration fades and instinct prevails. That’s what happened in the mid-1990s, while Smith was prosecuting a gang leader. One day a young man confronted Smith at the courthouse and urged him to drop the case or, well, he knew where Smith lived. Smith went after him, shouting profanity and following the man until he disappeared. Even after police later arrested the man for carrying a shotgun near Smith’s car, he still shrugged it off.
A few months later, the same young man would admit to shooting a Maryland state trooper on behalf of a different gang leader. Three men had staked out the home of the trooper’s parents before ambushing him in his cruiser, shooting through the windshield and wounding him.
“It made me realize how dumb it was to not appreciate the reality of some threats,” he says. “My perception that this was a half-assed idiot was wrong. Wrong enough that if he would’ve employed the same level of deliberateness to me that he had done earlier for this guy, I’d be dead.”
He takes a breath.
“I don’t underestimate anyone,” he says.
'Be prepared to fight'
One morning last month, Smith was part of an NFLPA contingent that took the Acela Express from Washington to New York. Smith sat in the last row of the first car and busied himself, preparing and contemplating what he would say during a meeting with the NFL’s Management Council Executive Committee.
The union has, over the past two months, engaged in four negotiating sessions with owners on a new labor deal. Unlike a decade earlier, there’s hope that a war might be avoided, but Smith, as always, is skeptical. He’s riding into what might be his last battle, and colleagues can’t help wondering, if there’s an agreement in place months before the current CBA expires in March 2021, whether Smith might be disappointed, wondering whether he should have asked for more, whether he should have fought harder.
“When you go in there, you’ve got to be prepared to fight the sharks,” says Boone, who once hated Smith before getting to know him. “At the end of the day, you’d better have the meanest shark fighting for you.”
When the train stops at Penn Station, Smith is the last passenger to depart. He packs slowly and waits for everyone else to leave, part of his routine like the push-ups used to be. Eventually the car is empty, and he waits as long as possible to give inspiration a fighting chance against instinct. As he gathers his things, he presses a button that reveals the wallpaper of his iPad: a black-and-white portrait of James Baldwin, the last thing Smith sees before stepping off the train and entering the campaign ahead.