Inside the dual legacies of the NFL’s union boss

TWO OPTIONS FOR extending the NFL season were in play in fall 2019, and DeMaurice Smith seemed defiant in the face of one of them. Smith, the veteran executive director of the NFL Players Association, was standing before a room of players, part of his annual tour of locker rooms to deliver an insider’s update on negotiations with the league. A deadline was coming fast: The league demanded a new collective bargaining agreement by March 2020, even though the current one didn’t expire until early 2021. But owners wanted an early deal because they intended to enter into rights negotiations with their broadcast partners. With the invaluable leverage of guaranteed labor peace for another decade, the owners believed they could secure a 100% increase for broadcast rights, a windfall worth tens of billions.

The cornerstone of a league proposal in June 2019 had been to expand the regular season for the first time since 1978, from 16 to either 17 or 18 games. For years, management had floated a longer regular season, but the notion was always roundly dismissed by players — and Smith — as a cynical money grab that not incidentally would pose a greater risk to their health and safety. This time, the owners were serious.

And players stood in near-uniform opposition. They wanted higher salaries and better benefits for their current workload, providing labor for America’s most popular sport. Standing in front of the players, left hand in his pocket, right hand in motion, Smith captivated the audience the way he once did as a young litigator inside a courtroom. “My legal advice to you guys on that — I don’t vote — would be to say, h-to-the-hell f— no about 18 games,” Smith told players. “If we give them the right to dictate our work, nothing good is coming out of it.”

But 17 games? That, it turns out, was different.

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A FEW MONTHS later, many players felt as if the league was dictating the terms to De Smith — and nothing good was coming out of it. On the morning of Thursday, Jan. 30, 2020, Smith stood in a meeting room of Miami’s Nobu Hotel. The room was filled with 30 of the 32 player representatives, along with 11 executive committee members, plus union executives and staffers. A deal was close. But first, Smith, only days before his 56th birthday, had to discuss a concession that could potentially kill the deal and split the union: a 17th game.

Smith and his executive team already knew that adding another regular-season game was an epic and unpopular move. On Aug. 19, 2019, following negotiations with owners, union executive committee members in a confidential Slack channel discussed management’s latest proposal, which included a 17th game and the option for an 18th game down the road, in exchange for a 1% increase in total revenue: “Basic message: without more games, no changes in economic structure.” The proposal received severe pushback from some players; others wanted to know what concessions were in play. Negotiations had been suspended that fall, and it took a secret meeting in November between Smith and New England Patriots owner Robert Kraft at the New York City apartment of Philadelphia 76ers co-owner Michael Rubin to jump-start talks. During a Dec. 23 conference call between union executives and executive committee members, San Francisco 49ers cornerback Richard Sherman asked point-blank if the union had been negotiating with the league based on 17 games as a foregone conclusion.

“Yes,” Smith said.

Players wondered how the hell one possibility that Smith had cast in skeptical terms a few months earlier had suddenly become non-negotiable. Few player reps knew that in the 2006 CBA negotiated by Raiders Hall of Famer and legendary union leader Gene Upshaw, owners had won the authority to unilaterally expand the regular season to 18 games. Then, after management opted out of that agreement in 2008, Smith had negotiated language that an expansion could occur “only with NFLPA approval.” It proved to be a powerful bargaining chip. Now Smith had extracted a handful of concessions from owners for an added game, including more time off for players and an immediate 20% increase in a player’s minimum salary, to $610,000 a year.

In Miami, few player reps seemed to care that Smith had pulled off this nifty piece of negotiating, forcing management to pay for something that was once theirs. Smith warned the room that if the union rejected 17 games, players should be prepared for a lockout.

“It might last two to three years,” he said.

Many player reps felt the choice presented to them was hurried and binary, with little or no transparency. The distrust and anger that had built up over months between Smith and the players began to spill over as the afternoon wore on. Aaron Rodgers would soon publicly accuse Smith of “fear-mongering.” Smith believed he was only presenting the facts of a proposal and the likely consequences if the players said no. The meeting devolved, as many sessions had over the past year, into a shouting match between player representatives and their embattled leader — who seemed, to many, more aligned with management than his own union.

“THE FOLKS ON the other side of the table are killers,” DeMaurice Smith says from his Washington, D.C., office on a mid-October day. It’s a blunt assessment from a man who looks exhausted from the last battle while gearing up for the next one. Smith and the union had spent years preparing for the most recent round of CBA negotiations. He had traveled the country. He had waged loud, public wars with commissioner Roger Goodell while holding private lunches with him. Quietly, often without some of his player reps’ knowledge, he had met one-on-one with influential owners such as Jerry Jones and Robert Kraft, and endured months of union infighting. At the end, the CBA passed last March by a slim margin of only 60 votes, boosted by votes from practice-team members, the lowest-paid union members with the most to gain from the new deal’s terms. The CBA should have been a moment that defined the power not only of Smith, but of the labor force of America’s most popular sport, a once-in-a-decade chance to elevate NFL players into NBA players’ realm of compensation and influence.

But that’s not what happened.

Instead, after fashioning himself as the league’s foremost antagonist, Smith is now viewed by some in his own ranks and by some owners as an asset to management, according to interviews with team owners; current and former union, league and team executives; lawyers and agents; current and former players; and reviews of thousands of public and confidential documents. Smith’s opponents say he secured the new CBA while trampling dissenters within his own ranks, presiding over a union that commissioned a law firm to investigate a player rep who questioned his honesty. He benefited from a ratified constitutional change that made it more difficult for an outsider to even run against him, let alone unseat him. On top of it all, the NFLPA caved on the league’s two most vital issues: more games and another CBA that stretches forward a decade, a length of time rarely granted by labor unions. In what will likely be his last CBA, Smith delivered what football fans desperately want — more games and labor peace — but at a cost to the players that will reveal itself over time. “If we could,” says a longtime NFL owner, “every owner would build a statue to De outside their stadiums. That’s how good he’s been for our business.”

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HOW DID ROGER Goodell’s foremost public adversary come to be known by some of the commissioner’s bosses as an ally? Nearly a dozen years ago, Smith arrived in the NFL world as a little-known outsider. After Upshaw, a formidable advocate for players, died from cancer on Aug. 20, 2008, it seemed a foregone conclusion to league and union insiders that another former player or league lifer would be elected as the fourth executive director in the player association’s history. The favorites were former Philadelphia Eagles star and NFL executive Troy Vincent, former veteran defensive end Trace Armstrong and longtime league consultant David Cornwell. The long shot was Smith, then a 45-year-old partner in the Washington law firm Patton Boggs. He had no experience in sports business or labor law, but he was friends with former Washington great Charles Mann and served on the board for a charity launched by Mann and several former teammates. A search committee tasked with finding union candidates reached out to Smith.

With the help of George Atallah, a crisis communications specialist who would become the union spokesman, Smith pursued the job. And at the union’s election meeting at the five-star Fairmont Kea Lani hotel in Maui in mid-March 2009, Smith closed the deal. Over four days of discussions, he dazzled the room, emphasizing his corporate background, expertise with Congress, alliances with President Barack Obama and Attorney General Eric Holder Jr. — and willingness to “use every bullet in the cylinder” in shootouts with the league. On the first ballot, Smith was unanimously elected.

On one of Smith’s first days at work, he opened the desk drawer of his Washington office and found a handwritten speech. It was by Upshaw. Smith read the speech, written over two columns in neat, black ink. It felt like a talisman, and one line stood out to Smith as wise and inspirational — and as a warning: “Owners will always take a short-term loss for a long-term gain.”

Upshaw’s words were both a nod to the strength of the enemy — and a clarifier of Smith’s mission. His job was not only to notch wins at the negotiating table. It was to ensure that the league didn’t break the union.

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AMERICA’S GREAT UNION leaders, such as Walter Reuther at the United Automobile Workers, find ways to become more powerful than any CEO. In sports, Marvin Miller transitioned from running United Steelworkers to manhandling baseball team owners in a zero-sum game. Smith, though, walked headfirst into a buzz saw — not only as an outsider and a Black man in a room of nearly all white billionaires, but because from the start, he and Goodell were on a collision course. Goodell “loved” and “respected” Upshaw, according to a former senior league executive, but the commissioner was unsure of what to make of Smith, whom he saw as “just another lawyer, a pain in the ass.” For the new CBA, Goodell’s mission was clear: Owners wanted revenge after the 2006 CBA had lavished players with up to 57.5% of “total revenues,” as defined in the deal, though union officials now insist the players’ share, after owners’ deductions, was less than that but still north of 50%. The upcoming 2011 CBA negotiations were seen as a street fight over “who could f— the players worse,” one of the league’s negotiators says now. Owners bragged about a $4 billion war chest and hired an outside law firm, Proskauer Rose, that represented all four major American sports leagues and would help engineer four work stoppages, including the NFL referees’, in an 18-month span. Although this was Goodell’s first CBA negotiation as commissioner, he was a league lifer who had thrown elbows at the table before and, as commissioner Paul Tagliabue’s protégé, had developed a keen sense of the league’s business. This was Smith’s first. Goodell “grew up in the NFL, he grew up understanding the levers of power,” Smith says now. “We weren’t equals.”

The league set a mid-March 2011 CBA deadline, threatening to lock out the players if a deal couldn’t be reached. On March 11, inside the Federal Mediation and Conciliation Service building in Washington, owners presented a final proposal to players that cut deeply into their share of overall revenue but still increased players’ salaries because league revenues had surged. However, in the view of most owners, the league was still handing the players too large a slice of the pie. “It was a very generous deal, which the owners didn’t love,” a league executive says. Jerry Richardson, the Carolina Panthers’ owner at the time, offered to give the union time to debate the offer. The player representatives rejected it out of hand, with Smith in agreement, ensuring a lockout. “De wanted a percentage of the real pie, not a bigger percentage after the owners ate all they could,” a union official says.

Shortly afterward, owners went upstairs to join a group of team and league executives, who asked what had just happened. It would turn out the deal that the union turned down would have been roughly $1 billion better for the players than the deal they would cut months later, sources say.

Jerry Jones of the Dallas Cowboys took the floor: “Look, my daddy grew up on a farm in southwest Missouri. Every so often in the spring, the wind would come from a different part of the country, and the moon would set a different way, and the owls would start f—ing the chickens.”

Nobody knew where he was going with this story.

“The owls are f—ing the chickens,” Jones continued. “It makes no sense that they turned this down, but it’s a great thing for us.”

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AS THE OWNERS’ 132-day lockout of the players stretched the labor uncertainty from late winter into early summer, Smith settled into a dual role: aggressive public critic of Goodell and, inside the negotiations room, a details-focused information-gatherer and fierce advocate for his players. “I thought he did a really good job of exposing faults that the league knew were in the deal but didn’t want to admit,” says former Indianapolis Colts center Jeff Saturday, at the time a member of the union’s executive committee. Too often, though, Smith struggled to get his members onto the same page. It was an old labor story: No matter how many times Smith had implored players to save money, no matter how many lockout contingencies and war chests the union had allocated, labor needed a deal more than management. Smith saw it as his job to get the players, who have short careers and always want to get paid more money now, to understand the long-term stakes and prepare for the worst.

It became obvious that owners wanted to expand the regular season. In one contentious meeting, Richardson discussed the owners’ desire to add a 17th game — reminding the room that, under the terms of the 2006 CBA, the league could activate as many as two extra games without union approval.

“We’re not playing 17 games, Jerry,” said executive committee member Domonique Foxworth, who now works for ESPN. “It’s not going to happen.”

Richardson sat straighter in his chair. “We can make you. We don’t have to ask you. We’re being nice by not saying, ‘F— you, you have to do it.'”

“We’re being nice by not telling you, ‘F— you, we’re not playing,'” Foxworth responded.

“We’re being nice by not telling you, ‘F— you, we’ll play with replacement players,'” Richardson said.

“We’re being nice by not telling you, ‘F— you, good luck filling up stadiums with Ryan Leaf at quarterback,'” Foxworth replied.

It was getting out of hand.

“That’s a lot of f— yous!” Smith said, adjourning the room.

In July 2011, the lockout ended and, thanks in part to a negotiations room bond of trust formed between Smith and Kraft, a new CBA was completed. Owners were elated that the players’ share of revenue was reduced from a high of 57.5% to 47%. Smith gained ground on many key issues, from curbing owners’ ability to skim $1 billion of revenue off the top each year, to starting a defined pension plan at a time when many large corporations were doing away with them, to establishing a salary-cap floor — although some owners now say they were prepared to cede more ground on that issue. As the final touches were being put on the deal, there was a wide-ranging discussion about players who had tested positive for recreational drugs before the lockout and players who were facing suspensions during the lockout. Smith was trying to negotiate a “grace period” for players who might have used drugs during the lockout.

Adolpho Birch, then a league executive, stared at the union brass, wondering if anyone would say something.

“Bueller?” Birch said. “Bueller?”

Finally, Birch said, “No player could have tested positive during the lockout, because we weren’t testing players during the lockout.”

It was an awkward moment at the end of a brutal negotiation. From Smith’s perspective, he won in two key areas. One was public and obvious: a reduction in the number of total practices — and practices in pads — for the players, though some owners and executives later said the league, hypersensitive to the optics of the head-injury crisis, would have given that up relatively easily anyway. The other union win was quiet and under the radar: Smith persuaded owners to agree to seek union consent for an expanded regular season.

But the owners’ gains, cemented by the certainty of a 10-year deal, were monumental: a lopsided salary-cap system that rewarded franchise players with generational wealth but squeezed the large middle class of players, and players would continue to work without guaranteed contracts. More importantly, the deal would help the value of team franchises further skyrocket. An adversary of Smith’s, former player Sean Gilbert, estimated that $10 billion would be shifted from the players to the owners during the deal’s decade. A league executive says now that the 2011 CBA amounted to, in the sports world, “the biggest transfer of wealth of the 21st century.”

It was exactly what Upshaw had warned of: The league took a short-term hit for a long-term gain.

IN NOVEMBER 2011, the union’s 11-member executive committee considered a proposal to pay Smith a $1 million bonus for his CBA work. The bonus required a majority vote of the committee, one that wouldn’t come easily. Already, Smith’s compensation had become a sore spot, for him and the committee. After winning the job, Smith had worked the first few months without a contract before earning $1.61 million his first full year, union documents show, an initial salary that had disappointed him. He had expected a compensation package near the annual $6 million paid to Upshaw. A majority of the executive committee members believed Upshaw was grossly overpaid and granted Smith a package worth far less.

Some members, including Scott Fujita and Charlie Batch, were opposed to paying Smith the $1 million bonus, according to executive committees’ email exchanges. Led by Fujita, they argued that it should be paid only for “exemplary performance” and that Smith’s performance during the CBA had fallen short of that standard. However, Tony Richardson and Drew Brees pushed hard for Smith. Their arguments prevailed — Brees’ endorsement and lobbying helped push it over the line. Asked about whether he was aware of the contentious debate among the reps over his $1 million bonus, Smith now says, “I don’t know anything about the vote. I don’t get a vote.”

There are other ways Brees proved to be one of Smith’s most vocal and invaluable backers. Publicly, Brees echoed Smith’s harsh criticism of Goodell in the media, a powerful player visibly in Smith’s corner, especially on high-profile player disciplinary matters. And even on below-the-radar, complicated issues, Brees proved to be an influential union ally. In 2014, the NFLPA asked agents to warn their clients that signing with the Saints could subject them to unfavorable workers’ compensation benefits. A Louisiana bill would dramatically limit benefits paid to players hurt outside the regular season. At the urging of Smith and other union officials, Brees and the Saints’ players representative publicly denounced the measure that their own team had endorsed. In a statement, Brees declared the legislation “is not good for Saints players, not good for our team or other sports teams in Louisiana and not good for our state.” Weeks after Brees publicly opposed the bill, its sponsor pulled the legislation.

Some former union executives and executive committee members were well aware of Brees’ strong support of Smith when they looked at an entry in the union’s own annual reports filed with the U.S. Department of Labor: It appeared that not long after Brees joined the executive committee in 2008, the union had begun paying him enormous sums of money for that work — more than $2 million some years. And during Brees’ seven years on the executive committee, from fiscal years 2009 to 2015, the union paid a total of $9,619,965 to Brees, a company that he owns and to his foundation, according to the union’s annual reports filed with the Department of Labor. The NFLPA paid Brees $2,423,504 in 2010, and in 2011, the year of the lockout and the new CBA, a total of $961,532. The payments are in a column denoting Brees’ work as an executive committee member, the union records show.

The payments to Brees were not hidden — they were public record — but a strict reading of the federal paperwork shows they far outpaced those received by any executive committee members, including Foxworth and Saturday, who in 2010 are listed getting $5,300 and $15,461 respectively, which was primarily reimbursement for expenses. During a budget meeting between union officials and a handful of executive committee members, a few players asked about Brees’ $2 million compensation listed under the union’s column for executive committee work. They were told the Brees money was from NFL Players Inc., the union marketing arm that pays players for appearances and endorsements, sometimes exceeding seven figures. It was merely an accounting issue, union officials explained.

The Players Inc. explanation was viewed skeptically by some union reps and Cyrus Mehri, who in 2017 was preparing to challenge Smith in the union’s scheduled election in March 2018. Mehri, a respected civil rights lawyer, had won enormous settlements on behalf of workers against companies such as Texaco and Coca-Cola, and helped create the Rooney Rule. Mehri and his team studied the union’s public filings and were “stunned” when they saw the Brees payments. “It knocked our socks off,” Mehri said. “We checked the Upshaw years and found nothing remotely comparable.”

ESPN examined the filings and sought opinions from several labor experts and found no evidence of wrongdoing, and found that the paperwork was likely legally completed. No experts wanted to speak publicly about the matter because they didn’t want to get embroiled in any dispute, but they said the filings could have more specifically accounted for the Brees payments. The documents include no mention of Players Inc., only payments for “executive committee work.” “From a transparency perspective, it’s confusing, to say the least,” says one veteran labor expert who reviewed the documents.

Smith and Atallah say that the vast majority of union money paid to Brees was strictly for Players Inc. duties at the height of his celebrity and earning power. Atallah said Smith doesn’t steer Players Inc. money to star players, saying the union has “zero discretion” on how much star players can earn for endorsements and marketing opportunities. And in fact, Smith says, Brees ranked 12th among NFL players in total Players Inc. payments, trailing the total sums earned over the past decade to stars such as Tom Brady, Peyton Manning and Tony Romo, usually paid to limited liability corporations connected to the players. Citing confidentiality, the union declined to break down the payments to Brees or any other player, but Atallah calls any suggestion of impropriety “dangerously false.” Smith and Atallah say the payments are listed appropriately and prepared by the union’s finance department in conjunction with its external auditors. They say the union has had clean audits for the entirety of Smith’s tenure and they “have never been approached to correct or even clarify any of our filings” with the Department of Labor. “Being a union president or executive committee [member] is a volunteer position,” Smith explains. “You get $0 payment, no salary, no stipend. … So Drew Brees, when he was on the executive committee, happened to be at the height of his marketing powers. … And therefore his combined equal-share payment, licensing, royalty and appearances fees were in the top 20 in the NFL. …. I mean, it literally is that simple.”

Brees’ agent, Tom Condon, agreed that any question about the payments is “solely a ministerial reporting issue regarding the union’s filing with the Department of Labor and where Executive Committee members’ Players, Inc. monies are reported on the form and where those same players’ … monies are reported when not on the Executive Committee.”

A UNION LEADER has a nearly impossible job, trying, despite limited power, to please a spectrum of people and personalities. One of the few ways for Smith to rally the players was to turn Goodell into the enemy. Smith sought out a public platform as a willing and aggressive antagonist of NFL management — and, in some cases, of his own CBA. Smith seized on two issues: players’ health and safety, and Goodell’s absolute disciplinary authority. The specter of a looming expanded regular season was very much on Smith’s mind, as if he were already drawing battle lines for the next CBA negotiation. “The 18-game season is a perfect example,” he told ESPN in early 2013. “It’s a revenue-generation idea that benefits the owners on the front end because it creates more revenue. And then it benefits owners on the back end because a longer season means more injuries and fewer of our players would get into a state of vesting where owners would have to pay for their pensions. It is diabolically brilliant. It also happens to be completely inconsistent with health and safety.” But Smith had inconsistencies of his own on health and safety. After reducing the players’ practice load in the 2011 CBA, Smith offered little initiative on health and safety matters, critics complained. He was content to remain on the sideline and allow the billion-dollar concussion litigation against the league to be led — and eventually settled — by plaintiffs’ attorneys. But Atallah says, “Our union is as proud of our record on player health and safety as any of our other accomplishments.”

Smith was far more comfortable relying on a playbook that challenged the league on Article 46 of the CBA, better known as the long-standing rule that granted the commissioner absolute power on disciplinary issues. In a self-proclaimed campaign to “protect the shield,” Goodell wielded the power with such ruthlessness that the commissioner’s discipline of star players ballooned into cultural touchstones, transcending the sports world. After Goodell handed down the Bountygate punishments against the Saints, Smith declared that “a bounty program never existed” and dismissed as “shoddy” the NFL inquiry that suspended the team’s general manager, head coach, two assistants and four players. Following the domestic violence suspension of former Baltimore Ravens star Ray Rice, Smith blasted NFL teams for failing to re-sign the running back, saying, “This, unfortunately, is a league that has a history of blackballing players.” And during the protracted federal court fight over Brady’s four-game Deflategate suspension, Smith said that by failing to grant Brady a fair hearing, Goodell had acted like “a bully” in a league that “has a history of being bullies.”

Players loved Smith’s tough talk but some saw it as empty, complaining privately that nothing would change as long as Article 46 remained unchanged. Sometimes Smith appeared to be fighting alone. Sometimes he had all of New England or New Orleans behind him. Regardless, Brees always publicly backed up Smith — and he did it in a fulsome way few, if any, other players did. “I think we would all agree that [Goodell] definitely has too much power,” Brees told Sports Illustrated during Deflategate, the type of remark the Saints quarterback made routinely over the years. Goodell, Brees said, “is judge, jury and executioner when it comes to all the discipline. I’m not going to trust any league-led investigation when it comes to anything. It’s not transparent.”

A favorite page of the union playbook began to emerge: Smith would follow his harsh criticism of Goodell with legal action, arguing in court that the absolute authority he had agreed to in 2011 was now unfair and being abused by Goodell. From disciplinary cases involving players such as Adrian Peterson and Ezekiel Elliott, Smith dispatched high-priced legal teams to challenge Goodell’s punishments and power — but ultimately lost in court nearly every time. Legal costs ran into the tens of millions of dollars, according to NFLPA annual spending reports filed with the Department of Labor. Since Smith became executive director in 2009, the union has paid a total of $79,514,058 in legal expenses, the reports show. And of that amount, the NFLPA spent a total of $55,675,006 representing issues arising directly from disputes related to the CBA, the reports and analysis show. By comparison, Major League Baseball’s players’ union spent $12.4 million from 2009 to 2016, and the NBA’s players’ union spent $15.1 million over that seven-year period, both players’ unions’ financial records show.

“We have the largest membership of professional athletes in the country,” Smith says. “If you open up any case law book, you’ll see that virtually every sports law major case is fought by the NFL Players Association.”

To union critics, the total spending on fees for outside law firms amounts to a massive, inexplicable waste of money, particularly when considering how often the union loses in court to the NFL. Peter Ginsberg, the lawyer for Rice, said he was stunned to discover that Smith had set up a “parallel investigation” of the running back’s suspension proceedings, with so many lawyers present for each meeting that it amounted to overpriced overkill. “De brought on, for no apparent reason, other expensive lawyers to supplement more-than-competent lawyers like [veteran union lawyer] Jeff Kessler,” Ginsberg says. A former veteran union official criticized the union’s “wasted spending” on legal clashes and Washington lobbying firms. “He’s an attorney, he likes chaos,” the former official says. “When things are still, he has nothing to do. He needs a fight. He creates battles.”

League executives also suspect Smith of deploying other tricks of war. Smith would fail to call when he and Goodell had a talk scheduled, the executives say. He then would call Goodell later in the day, when the commissioner was in another meeting and, executives believed, subsequently leak word to the media that Goodell was too busy and not returning his calls, as if to underscore how little the league cared about its players. It’s a practice that union officials deny but league executives believe repeatedly occurred, even if they lack proof. Smith became friendly with the league’s most influential and powerful owners, such as Jones and Kraft, as a way, he says, to “find out from individual owners what’s the motivation behind why talks aren’t going well.” But he and Goodell, despite multiple similarities in their jobs — both must try to marshal finicky constituencies despite limited authority — failed to click. During one meeting in 2014, Smith told Goodell that the union had cut a lucrative deal with the apparel company Fanatics without the NFL’s consent “just to see his head explode,” Smith later told a confidant.

“It was unconventional,” a former league executive says. “And exhausting.”

Even so, most owners couldn’t have cared less if Smith irritated league executives. Team valuations spiraled far beyond even the most bullish owner’s expectations. From the 2010 to 2019 seasons, for example, the Dallas Cowboys’ valuation skyrocketed by $4.5 billion to a league-high $6.4 billion, according to a Sportico report. But over that same period, team salary-cap increases lagged far behind, increasing from $120 million in 2011 to $198.2 million in 2020, though those figures don’t include benefits. Team revenues have also outpaced players’ salaries; the Cowboys’ annual revenues have grown from nearly $500 million in 2011 to $980 million in 2019. Both owners and many players knew that the clubs’ valuations and revenues gulf kept widening, though Smith’s salary has doubled, from $1.6 million his first year to nearly $3.2 million last year. “They’re laughing,” a veteran agent said of the owners. “How come every franchise’s equity value has gone through the roof and the players’ salaries haven’t followed?” To that criticism, Atallah says, “It’s foolish to think the players want the clubs to lose value or revenues, since we share in that growth. If you want to criticize De for doing a deal that allowed owners to make money on the one hand, you have to accept that the deal forced owners to pay out players on the other hand at a record rate.”

Union officials argued that players’ shares of revenue, when including salaries coupled with benefits, have in fact nearly kept pace with the jump in team revenues. But the defeats in court and at the negotiating table had hurt Smith’s standing and credibility among some leaders inside the union and among some veterans and Hall of Fame retirees. And with his position up for reelection every three years, some in that influential group began saying perhaps Smith was worth replacing.

IN MARCH 2015, Smith learned a quick but vital lesson about the fragility of his job security. Eight challengers lined up to stop his reelection bid: three lawyers; two former players; a retired U.S. Navy vice admiral; a sports and entertainment executive; and Jason Belser, a popular union insider working as the NFLPA’s senior director of player services and development. To get on the ballot, the NFLPA constitution required a challenger to secure the nominations of at least three team player-representatives. It wasn’t lost on Smith and his allies that a vast majority of player reps wanted the election, set in mid-March in Maui, to be a wide-open affair.

Over two days of contentious meetings in Maui, the candidates made their presentations to the assembled player reps, challenging Smith on predictable grounds of player health, the CBA and fruitless expensive fights with Goodell. Belser seemed to gain momentum with some player reps — but he was derailed by Smith loyalists’ accusations that he had puffed up his résumé, an accusation Belser denied. Smith’s impassioned closing argument won him the required 16 votes of the 31 team reps — the Buffalo Bills’ rep abstained — and another three-year term. It was hardly an endorsement. “A clown show,” a senior union official now calls the two-day session. Privately, Smith’s allies vowed it would be the last time an upstart got the chance to come out of nowhere to claim the job, the way Smith had in 2009.

Not long after Smith was reelected, union executives and player reps began discussing amending their constitution, changing the rules on how the union hires — and maintains — its leader. A year later, in March 2016 at the union’s annual Hawaii meeting, the new election procedures were formally considered: They would put the power to offer the executive director a contract extension in the hands of a 14-member selection committee. If the selection committee unanimously agreed, the incumbent would be extended another three years in office without having to run for reelection.

The sweeping constitutional change served its intended purpose. Cyrus Mehri, who had garnered the support of more than a dozen Hall of Famers, including Jim Brown, announced he was running for executive director during an August 2017 profile of Smith by HBO’s “Real Sports with Bryant Gumbel.” In that piece, Gumbel asked Smith what he liked about the 2011 CBA.

“All of it,” Smith replied.

“I just thought it was a pathetic response,” Mehri says now. “It’s a combination of arrogance and ignorance to say that.”

A few days after the HBO broadcast, Mehri met in his Washington office with Charles Mann, who handed Mehri a document. It was the amendment to the NFLPA constitution on elections. A union official had slipped a copy to Mann. “There will never be another open competition for executive director,” Mann told Mehri.

Everything about the rule change was suspicious to both men, from its merits to the fact that the old election process was still on the NFLPA website 10 months after it had been changed. Union leaders felt that even if the website wasn’t updated, the rule wasn’t exactly a secret. ESPN had reported on it. Still, the executive committee changed the constitution during the regular season, when players were busy with work. Mann told Mehri that he saw no point in mounting a challenge to Smith, who he said now had the top job “for life.”

The way Mehri saw it, the constitution change was the continuation of a pattern. “The fix was so in — it’s so rigged,” Mehri says now. “They were afraid he could lose; they were afraid of competition.”

Mehri still tried to get on the ballot by following the union’s new rules. After all, he would need to persuade only one of the 14 selection committee members to stop Smith’s contract extension and force a vote of all 32 player reps. But Mehri says now that a scheduled dinner meeting in northern New Jersey with two selection committee members, Giants linebacker Zak DeOssie and linebacker/tight end Mark Herzlich, was canceled at the last minute. DeOssie texted Mehri, saying that he had been told by union officials that under the amended constitution, it wouldn’t be appropriate to meet with him. Mehri said he also attempted to meet with three other influential player reps on the selection committee — Ben Watson, Richard Sherman, Lorenzo Alexander — but none replied to his repeated text messages. “It was a lockdown — they clearly decided they didn’t want to talk with me,” Mehri says. “Like anything else, you can control 14 people pretty easily.” Mehri considered publicly raising the Brees payments and the election rule change, but he says now that he feared it would hurt not only his candidacy, but also the union as it headed into the 2020 CBA negotiations. “It could have been destabilizing, divisive, and presented the grave risk of destroying the union heading into negotiations,” he says.

Smith, though, dismissed Mehri as one of many outsiders who took shots at him and who he says exaggerated his chances of replacing him. Mehri was “a guy who was, as far as I know, never nominated to run for the job by a player,” Smith says. For his part, Atallah says he won’t dignify any of Mehri’s accusations. One aspect of the amended constitution required the executive director — in this case, Smith — to provide the new selection committee with his own report card of his performance, rather than seeking a grade from an independent source. When the union announced in September 2017 that the selection committee had unanimously granted Smith a new three-year contract, Joe Lockhart, then the NFL spokesman, congratulated Smith on Twitter. Lockhart said that the league had “productive” negotiations with Smith in 2011 and looked forward to more of the same in the future. It was a tweak masquerading as a kind gesture. Nobody at the league was disappointed.

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IN THE RUN-UP to CBA negotiations, Smith visited each team’s locker room. The meetings were long, sometimes two or three hours, and often at brutal times — such as after practice, when tired, distracted players just wanted to go home. Some players complained that Smith is a lawyer who can’t understand life in the locker room because he never played pro football; they yearned for a union chief who is a former NFL player. Still, Smith was strong in front of a room, engaging and energetic. He had been in his job longer than nearly all NFL players had been in theirs, and so he was an institutional authority. Executive committee members sometimes wanted Smith to delve deeper into policy details, but he preferred to stay at a 10,000-foot view. Nearly all players were preparing for a labor battle for the first and likely only time of their careers.

Smith implored players to save their money in the event of a strike or lockout in 2021. He was preparing for those outcomes himself. The union had amassed a $600 million war chest, a mix of players’ dues and withheld revenue from licensing deals — enough, at the executive board’s discretion, to cover all players’ salaries and union operating costs during a relatively short work stoppage. “We’re sitting on a lot of cash,” Smith often told players and others. At one point, he said the league was “desperate” for new revenue; Goodell’s oft-stated goal is $25 billion in annual revenues by 2027, a goal within reach when considering the upcoming gigantic increase in TV contracts and multiple new revenue streams from the nationwide push for legalized sports wagering. Smith knew the easiest way to unleash an avalanche of fresh cash was an expanded regular season and playoffs. Behind the scenes, he floated his own plan: shorten the regular season from 16 games to 14 and add four wild-card teams. “A Super Playoff System,” Smith called it. He had privately pitched the idea to Kraft and Jones, among others, but the owners were never going to contract the regular season.

Problem was, once the union decided to hear out the league on a non-negotiable expanded regular season, the owners had the upper hand. Smith countered the league’s 17-game proposal by seeking a larger share of total revenue, up from 47% to 50% — a longtime goal of the players. The league replied with an increase of the union’s percentage to 48% — but with more work.

“That 48% was tied to a 17th game,” Smith told players.

There were two catches, Smith explained. One was that each player wouldn’t be compensated a regular game check for the extra work; an estimated $250 million would be split among 32 clubs. “That 250,” Smith said during his autumn 2019 locker room tour, narrowing a gap between his hands, “gets small. So the question is: Does all that extra work, all-inclusive, make sense for the economic payoff?”

The other was that a 17th game was only the beginning. “But, oh, there is more!” union executive Don Davis told players at one point, describing the league’s proposal. “We’re gonna give you 1% more, we’re gonna have you play an additional game, but we also want the right to play an 18th game whenever we so choose.”

None of these outcomes appealed to many players. Smith was back to facing the same issue he had in 2011. The league wanted unilateral rights to expand the season, leaving Smith to characterize, and perhaps redefine, what a win would be for the union.

BY LATE WINTER of 2019, an offensive tackle named Russell Okung had grown dismayed with the process of planning for CBA negotiations — and with Smith. As a Los Angeles Charger, he had run for the executive committee in March 2018 on a platform of “transparency and communication.” But Okung quickly became disenchanted by the union’s leadership on a host of issues, ranging from Smith’s tepid support for Colin Kaepernick’s collusion lawsuit against the NFL to the goals and tenor of CBA negotiations to procedural practices. Article V, Section 5.14 of the union constitution required adherence to the parliamentary procedures known as Robert’s Rules of Order, including a longtime union practice of keeping the minutes of meetings. But executives didn’t enforce the rules, citing a need for confidentiality. “It felt deliberate” to keep people in the dark, Okung says.

A year of tension came to a breaking point in early 2019, when union leadership and various players met in Key Biscayne, Fla. On March 11, former Chiefs linebacker Andy Studebaker hosted a two-hour breakout session for 33 players, including Okung. Studebaker, one of the union’s player directors, stood near a 2×3-foot flip chart and wrote union negotiation CBA priorities as the room suggested them. Okung offered what he felt were creative ideas to pursue in the next CBA, including 50% guaranteed contracts, lifetime benefits and shortening rookie contracts from four years to two years. But he had a premonition that the priorities listed in the meeting wouldn’t be ultimately passed up the chain to Smith.

Okung took out his phone and pressed an app that recorded audio.

Two months later, on May 14, Studebaker held a meeting at the Chargers’ facility in Costa Mesa, Calif., with most of the team in attendance. Studebaker listed union priorities. Okung was furious. None of the ideas he had raised were included. He asked Studebaker where the ideas had come from.

The breakout meeting, Studebaker replied.

Studebaker tried to continue, but Okung cut him off. “Where the f— are the things on the list?”

Studebaker replied that he had presented the same priorities to other teams. Nobody had objected.

“That’s not the complete list!” Okung said, holding up his phone. “Guys, I have the complete list. … I have the list because I recorded the meeting.” Most people in the room were stunned. At 12:36 p.m. that day, Davis texted Smith and other union executives: “RO just told the LAC that he recorded the breakout meeting!”

Union leadership was fed up with Okung. The union commissioned an investigation into Okung by Winston & Strawn’s David Greenspan, a respected lawyer who had served on Kaepernick’s legal team. Greenspan’s report was issued on June 27, under a banner that read “Privileged & Confidential.” The report called Okung’s recording not only a “breach of confidentiality,” but also an expression of “defiance” and concluded that Okung had violated the union constitution. Greenspan cited a membership vote that prohibited secret recordings and superseded Robert’s Rules of Order, hinting that by failing to disclose to the room that he was recording the meeting, Okung also had “potentially” broken Florida’s Security of Communication Act, a third-degree felony. Okung considered the investigation a blatant attempt to silence him. Echoing a charge Smith often levels against the NFL, Okung questioned the inquiry’s fairness and independence, owing to the fact that the union had paid Winston & Strawn $3,120,395 in fees in 2018 — among the highest amounts sports unions paid to one law firm in a single year. Most of all, Okung felt he had been threatened with criminal prosecution and union sanctions for upholding his fiduciary duties — a topic on which he declined to comment.

Smith didn’t want disciplinary action taken against Okung. But a clear message was sent to the membership that dissenters would be targeted. Okung would try to defend himself in March 2020, days after it was announced he was traded to the Carolina Panthers. Twice, he filed charges of unfair labor practices with the National Labor Relations Board. He singled out Smith, accusing him of “subverting” the NFLPA constitution and citing a litany of alleged protocol violations, from excluding Okung and other executive committee members from negotiations to “threatening and chilling Mr. Okung and his right to speak.” And twice, the NLRB rejected Okung’s charges.

But by then, it was all but too late. Smith had secured the votes to pass the CBA — barely.

A CHAOTIC CBA vote followed another chaotic CBA negotiation. Owners deployed various tactics. John Mara of the Giants pleaded with the players to understand that owners weren’t making nearly as much money as the players had suspected. (Teams’ books are private, except for the publicly owned Green Bay Packers, which shows 2019 revenue of $506.9 million and $400 million in the bank.) Kraft reminded the union that both sides benefited from long-term labor harmony. On Feb. 20 of last year — after details of a proposed 10-year agreement, including a 17th game and an expanded playoff format, had been leaked to the media, which quoted league and union executives calling it “transformative” — owners approved the new deal.

The idea of more football was catnip to fans. Smith knew this, often telling friends with a laugh, “A football fan is like a crack addict who will never quit his habit.” And some players and agents opposed to the CBA viewed the avalanche of positive media coverage about an expanded season as a flagrant attempt to jam them. Surprisingly, though, it wasn’t only management backing them into a corner. It was also, some players and agents suspected, De Smith. Some team reps and star players were furious that the 17th game had become the starting point for negotiations. They also felt the owners had not given them nearly enough in exchange for the extra workload and that the public momentum quickly pushing a union-wide vote in March benefited the owners far more than them.

The day after the owners’ near-unanimous approval, the union’s executive committee rejected the deal by a 6-5 vote, primarily because of opposition to the 17th game. Union officials were surprised that it was rejected, though they say the vote was advisory and symbolic. Later that day, the NFLPA board of representatives — 32 team representatives — postponed a vote. Owners were stunned. “We had been working off 17 games since August,” one owner says. “They agreed to the 17th game.” On Feb. 25, executive committee member Lorenzo Alexander changed his support from a “yes” to a “no,” upping the total of executive committee members against the deal to seven. On Twitter, a flood of superstars — Russell Wilson, Aaron Rodgers, J.J. Watt, Todd Gurley — voiced strong opposition, arguing against the expanded season and the 10-year length of the new deal. It was a disaster for Smith.

An owner who is close to Smith says now that “De didn’t do anything to communicate” with the players. But on his desk, Smith has a binder as thick as an offensive playbook filled with every Slack conversation with player reps and others during the monthslong negotiations, though he declined to share its contents. Every player had a copy of the league’s proposal, including the 17th game, since August 2019. The added game was part of Smith’s fall speech to teams, though in those stump speeches, some players ended up recalling their leader’s tough talk more than the fine-print details. “I know what the facts are,” Smith says.

As if in concert, league and union executives seemed to clash with the game’s superstars, emphasizing through favored media channels the ways they said most players would benefit from the proposal. “This is upper-class players holding out to the detriment of the rank-and-file,” one owner said at the time. The owners’ strategy of pitting players against one another proved successful, as lower-paid players far outnumber the high-earners. “Management is trying to drive a rift between us,” Okung told his fellow player reps.

By then, some owners were saying they were over the union and Smith. And not every owner felt the CBA was as good for them as it might have been. “Some feel like we’re giving up too much for certainty,” one owner said then. The players’ board of representatives voted 17-14 in favor of the deal, with one representative abstaining — four votes shy of the two-thirds majority required by the union constitution to send an amended CBA to a full player vote. A deal suddenly seemed dead. Owners made it clear that this would be their last, best offer. Union leadership pushed to move the CBA to a full vote of all union members despite lacking the support of the executive committee or a two-thirds majority of player reps. After consulting outside labor counsel, Smith concluded that despite some lawyers’ reading of the vaguely worded constitution, all players could still vote on the full CBA despite the board’s failing to pass it by a two-thirds majority because it was considered by the union to be a new CBA. Okung disagreed with that conclusion and immediately filed an unsuccessful Unfair Labor Practices charge with the NLRB.

Then, just as all NFL players began a weeklong voting process, the world stopped. On March 11, the World Health Organization declared COVID-19 as a global pandemic. Lockdowns ensued, and the sports world halted. But during the NFL offseason, business continued. Free agency loomed. Management and union officials reminded players that a recession might be on the horizon, which could impact the upcoming broadcast rights negotiations. On March 15, with practice-squad players casting their votes, the new CBA was passed, 1,019 to 959 — a razor-thin, 60-vote difference. “Can’t believe we agreed to that lol,” then-Colts tight end Eric Ebron tweeted. “We can only play this game for so long and y’all didn’t want everything we could get out of it? …. 2030 y’all do better.” Nearly 500 union members didn’t even bother to vote. And among those who did vote, some players had instant buyers’ remorse and asked if their vote could be changed. The union said no. Smith had won — and his victory would hold up against legal challenges from Okung and Panthers safety Eric Reid, who was cut shortly after that and did not play during the 2020 season.

Reviews of Smith’s performance on the new CBA were mixed. Joe Banner, a former executive with the Eagles and Browns who helped negotiate the 2011 deal, felt Smith had done a good job, raising the split of revenue players received from 47% to 48.5% with the 17th game approved. But Andrew Brandt, a former Packers executive and agent, said Smith should have extracted more for the 17th game, considering the enormous boon to the league and its broadcast partners. Brad Sohn, a plaintiffs attorney on the head-injury lawsuit against the league, said the new deal “puts accountability for numerous health and safety issues on life support.”

“I wasn’t real, real happy about the way things went down,” said Aaron Rodgers, who bailed on being the Packers’ player rep in November.

Smith privately conceded that some of his critics were correct but also felt he had pulled off a feat of negotiating by extracting concessions for an expanded season the league had sought for more than a decade — not to mention long-term security at a time of economic calamity. He might not have prevented an expanded regular season, but he did limit it, preventing the league from increasing beyond 17 games without union consent. “I’m proud of all of it,” he says now.

As the CBA was being voted on, though, Smith was already looking beyond it. On the Friday before the deal passed, Smith ordered a book on the 1918 flu pandemic, “The Great Influenza.” It arrived Monday. He finished it in 72 hours — and formed a COVID-19 committee as he read. “I was terrified,” he says now.

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THIS SUMMER, FOR the second time in less than a year, some players believed Smith had leverage over the league. An estimated $9 billion was on the line if the NFL had to cancel its season due to COVID-19. If it played games in empty and nearly empty stadiums, the league was looking at a $4 billion to $5 billion drop in revenues, which would impact the salary-cap formula — and, perhaps, the negotiations for lucrative new broadcast deals. Once again, the league and the union were at the negotiating table, this time virtually. In Zoom sessions, the league proposed taking a 35% escrow out of players’ salaries to help manage costs. The union laughed. There was concern within the union that the league would pull the deal it had just ratified, cancel the season and return to negotiations in 2021 with players out of work for a year and in a weaker position. But the toughest issue ended up being the salary cap, which is based on league revenues. The league preferred to incur a one-time cap drop from $198.2 million this year to no lower than $180 million in 2021, and then have the cap rebound to $200 million or a bit more in 2022. Many players wanted to spread out the losses over more than two years, keeping the cap — and spending on player salaries — higher now.

The cap was one of many topics on July 17, when owners and top league executives convened for a videoconference to discuss confidential plans for the season. Only one representative per club was allowed. Goodell made it clear he wanted to find a safe way to play through the pandemic. Goodell, chief medical officer Allen Sills and general counsel Jeff Pash did most of the talking. Goodell called the situation “volatile” and implored owners to not fight with governors who wanted few or no fans at games.

“Don’t force it,” Goodell said.

Goodell was steadfast in his belief that the league had proper health protocols and a solid salary-cap plan, even if the details had yet to be finalized with the union. Some owners felt Smith had lost many of his players and held less power than he did in March. Mentions of the union mostly centered on a plea for nobody to leak details of the call — “We’ll lose leverage,” one owner said — and a brief discussion about Smith’s insistence on daily testing for the players. The league was lukewarm on daily testing, citing COVID-19’s minimum 24- to 48-hour incubation period, and preferred to test every other day. League executives seemed frustrated that union talking points included both a concern about taxing the general public’s coronavirus testing resources and an insistence on daily tests. But it was a minor issue: In the coming weeks, the league would agree to daily testing, handing Smith a talking-point win.

Toward the end of the call, everyone seemed exhausted — by the stress of the pandemic, a long year of negotiating with the union and never-ending videoconferences. But first, Vikings owner Zygi Wilf wanted to speak. “So, we’re opening?” he said.

“We plan on opening,” Goodell replied, slightly perplexed by the question.

“Should we do another one of these calls when things are agreed to?” Wilf asked, referring to the union.

“Sure,” Goodell said, sounding tired.

Jones then unmuted from his $250 million super-yacht, anchored off the Washington state coast, and argued that the league needed to be declarative that the season was starting on time: “Our body language needs to reflect confidence.”

“Well said, Jerry,” Goodell said.

The message was clear: The NFL was going to start the 2020 season on time and had every intention of playing every game through the pandemic. The union had to get on board. A week after the call, both sides amended the new CBA and agreed to a salary-cap structure. Although Smith felt he had won concessions — the revenue losses would be spread out over four years rather than two — many team cap specialists felt the league had won, again. If there had been a flat salary cap for three or four years, teams wouldn’t pay big money for free agents. Smith and union executives argued that even with a one-year hit, smart teams would be able to pay big salaries to stars and keep younger players happy with the bump in pay from the new CBA. The middle class of players would be squeezed — for the second time in Smith’s tenure. It was the most recent reminder not only that the NFL is still an owner’s league, but that playing in the most popular sport doesn’t guarantee being represented by the most powerful union.

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ON AN OCTOBER day, De Smith sits at his desk, looking on Zoom like a man who might not have won all of the time but who had certainly survived. It’s been a marathon session of discussing his record, in a long year of brutal negotiations, in a long stretch of trying to keep his family, staff, and players safe. Within days, former players Don Majkowski and Aveion Cason would amend an ongoing lawsuit against the league and union, claiming that protections for retired players were illegally stripped from the CBA — and asserting the deal should be invalidated and voted on again. There are rumors in ownership circles that Smith is angling for a way out, ready to hit the speaker circuit or write a book or do anything but trade barbs with billionaires and endure arrows from members of his own ranks. But when he’s asked about it, Smith speaks in the language of many Americans in the midst of a global pandemic and economic recovery: He’s just grateful to have a job. The past year has clarified many things for Smith. He says he’s proud of the union’s record on diversity, proud that the revenue from Players, Inc. has doubled during his tenure, proud to partner with Harvard on health and safety initiatives — and proud of his fighting. Indeed, the aspect of his job that you’d think would wear on him most has had the reverse effect.

“I like the combat,” he says. “It’s not for everybody.”

But the combat faded as the season went on, replaced by something resembling a partnership. On Super Bowl Sunday, Smith was standing with Goodell on the field before kickoff, chatting behind masks, the second time in a few days that they appeared together publicly. On the Thursday before the game, Smith joined Goodell on stage for a news conference, and after it concluded, the two men kept talking and laughing. Aides told them it was time to go, but they continued their chat, in no rush to leave each other’s company. The union posted a photo — “Took a global pandemic to bring them 6 feet apart,” Atallah wrote on Twitter — and the league tweeted out another one on Super Bowl Sunday, lauding the “unprecedented collaboration” over this past year.

Once again, the league had taken a short-term hit for a long-term gain, just as Upshaw had warned. His words are now laminated and in a display case in the lobby of the union’s office building. Smith walks by them each day on the way to his office, a reminder of the stakes. He has taken a short-term hit, too — with uncertain gains. But two things are clear: The league has not broken the union, and De Smith still has a job.

Seth Wickersham and Don Van Natta Jr. are senior writers for ESPN. Reach them at [email protected] and [email protected]. On Twitter, their handles are @sethwickersham and @DVNJr.