DeMaurice Smith was a fighter from beginning to end as NFLPA leader

Sometime in July, DeMaurice Smith will walk out of NFL Players Association headquarters for the last time, his 14-year tenure as executive director of the union officially over.

Earlier this week, the NFLPA announced that it had elected Lloyd Howell, a longtime executive at Booz Allen Hamilton, to succeed Smith, who had told player leaders in 2021 that his new contract term would be his last.

Smith was just the third-ever executive director of the NFLPA, a job he was unanimously voted into in 2009 after the death of Gene Upshaw, who had led the group for 25 years. A career litigator with experience in the U.S. Attorney's office before going into private practice, Smith was well-connected in Washington, but not in football.

He was then, as he remains now, a fighter.

Chatting with Yahoo Sports on Friday, headed back to the union's Washington, D.C. offices for one of his final times, he's asked what three things he's most proud of during his time with the NFLPA.

Smith readily begins a list.

"On a macro view, it was getting the union back to being a labor union," he said. "And that means fighting for the wages, hours and working conditions of our players. I know that sounds like a somewhat amorphous way of thinking about it, but there were things in the 2006 deal that we didn't like — we weren't able to control a lot of the money coming off the top and going to the owners, we didn't have the right to disagree with the league increasing the league up to 20 games for free, and when it came to the health and safety of the players, all of that was in the hands of the NFL and frankly, they weren't doing a good job.

"So taking a hardcore union view of this, it was, 'We are the workers, how do we instill more control over our own destiny?' And you saw that with everything from concussions to the protocols that I know were critical in keeping alive a young player [Buffalo's Damar Hamlin] that was fighting for his life on the field last year. I know that the things that this union did with respect to the health and safety and emergency procedures were vital in that success."

Smith didn't have long to ease into his role with the Players Association. In 2008, NFL owners had opted out of the the collective bargaining agreement signed just two years earlier because, in their eyes, the revenue share for the players — i.e., the people who are the game — was too high. They wanted to limit salaries significantly and avoid funding certain benefits for retired players.

Upshaw's death was a surprise; owners had months to get on the same page and prepare as the NFLPA worked to find capable candidates and ultimately vote one into the executive director role. Once Smith was chosen, he was thrown in with the sharks, charged with figuring out both who had the power on the owners' side and what the players wanted in the labor deal.

Owners locked players out in 2011 as negotiations droned on, a public fight that turned only after owners learned of a to-that-point secret insurance policy Smith had gotten permission to acquire that would have paid every player around $200,000 if there were no football that year.

The belief was that players' resolve would crumble as soon as they weren't receiving paychecks, particularly the rank-and-file clinging to spots at the bottom of the roster and/or earning the league minimum. The policy was intended to assuage that concern.

It never got to that point, and with Smith's guidance, players were able to get things they never had before, especially in the realm of health and safety.

For Smith, one of the biggest wins of the 2011 CBA was players getting the right to be paid for extra games. In the 2006 agreement, owners could have increased the regular season from 16 games to as many as 20 without paying the players anything for the extra work, just as they had done when they increased the regular season from 12 games to 14 and then 14 to 16. Now, the union has to approve any increase in the number of regular season games.

Honing in on smaller details he's proud of, Smith says one of the things he's happiest about is the NFLPA being the first American professional sports union in the American Federation of Labor and Congress of Industrial Organizations (AFL-CIO), a collection of prominent American unions. The MLB Players Association, MLS Players Association and NWSL Players Association and others followed suit.

"That's because I believe that all of these unions have to have an eye toward what's in the best interest of the workers without thinking first about this business as a sport," Smith said.

"And last, the infrastructure of the union increased dramatically. Our net assets that we use to protect our players, the revenue that's going back to players — I think when I started, a royalty check for players [via NFL Players Inc.] was less than $10,000, next year it will be $31,000. Minimum salaries were [under $300,000] but by the end of this current deal, our minimum salaries will be over a million dollars. And yes, that's tied to the increase in revenue, but it's more tied to our guaranteed share of that revenue.

Smith pauses.

"Can I add a fourth?" he asks.

Sure, he's assured.

"I'm proud of being a little bit of a nerd in this business," Smith said with a quick laugh. "I'll tell one quick story: When I came into this business, every conversation with every journalist, every GM and every player, every year, was how much was the salary cap going up?

"It wasn't until 2011 that we actually put a provision in the CBA of how much of that salary cap are we going to spend? And I don't really care that that's lost on a lot of people, but I think in a really simple way if you sit down in front of a prospective employer and he or she says, 'I have the ability to pay you $300,000,' are you happy? You shouldn't be. You should want to ask a second question, which is, I know you have the ability to pay me $300,000, how much of that are you actually going to pay me every year? That minor change alone" — getting a salary floor, or a minimum that teams must spend every year — "is billions of dollars swinging to players.

"Those aren't the kinds of things that make their way across the ESPN ticker, but for a group of people whose average career is three years, I think a union should focus on making those three years as profitable, as safe and as rewarding as your career can be."

The NFL and NFLPA entered into another 10-year agreement in 2020, as COVID was just beginning to rage and team facilities were shut down. It passed the player vote by a very thin margin.

For someone so deeply devoted to fighting, Smith is asked, why was that CBA signed a year before the landmark 2011 one had expired?

"When 2020 comes around, we poll our players on the things that are most important to them, and out of the top 15, we got 13 of them," he said. "If you're able to get 13 of your top 15 and not risk losing a strike, that's what the players voted on.

"The tough part of any union leader is not simply listening to what your players say, but watching what they do. And one of the things that I think has always been a barometer of the willingness of players to miss a paycheck is the number of players who go to OTAs for free. For free."

When it comes to the thing Smith wishes he'd been able to accomplish but didn't, he offers a surprising and candid response.

"I always wished that I had done a better job trying to get players to exercise both their will and their power," he said. "WNBA players got rid of one of their owners [Kelly Loeffler of the Atlanta Dream]. The U.S. Women's National Soccer team, they were talking about striking the World Cup. The World Cup. For the most part, those things have little to do with money and it has to do with exercising your will and your power.

"Despite what I would have wanted and asked our players to do, they are unwilling to not go to work for free. They're unwilling to pull all of the NFL stuff off their social media. You've seen groups of people like teachers and nurses and the workers' guild, and those people are walking away from salaries where they live paycheck to paycheck. Our minimum salary is over $800,000 a year.

"So is it a question of money? Or is it a question of will?"

As executive director, Smith's primary job was to get the players as much of what they wanted as he could. We can quibble about what the end results were, but the reality is he got them more than they'd ever gotten previously, even if it's clear he felt like they could have gotten more if they were willing.

As the saying goes, you can lead a horse to water, but you can't make him drink