From the moment he was elected head of the Players Association in March 2009, Smith has faced challenges on all fronts. After succeeding the legendary Gene Upshaw—the Oakland Raiders Hall of Famer who died in 2008—Smith had to establish himself as a credible leader despite his lack of experience in pro football. He was criticized for failing to take care of retired players. But the most pressing concern was the labor dispute.

In 2008, the league’s 32 owners decided they had gotten a lousy deal in their 2006 labor agreement, and they exercised their right to opt out. Owners complained that while NFL revenues jumped to $7.8 billion in 2010 from $4.8 billion in 2005, profit margins were being squeezed by stadium construction costs and rising player salaries. They argued that while players benefited from the investments by owners—in stadiums, the NFL Network, and NFL.com—the owners were stuck with the tab. So the owners are asking for another $1.3 billion of league revenues before players get their portion. (After owners take a cut for expenses, NFL revenue is divided roughly 60/40 between players and owners.) They also want two more regular-season games and a cap on rookie salaries.

The players see the proposal as an 18-percent pay cut and have asked the owners to show that they’re facing financial pressures by handing over the books. The owners have refused. If a new deal isn’t reached by the time the current agreement expires in March, the owners are expected to lock out the players.

Although Upshaw—Smith’s predecessor—was revered for engineering nearly two decades of labor peace, his players union was a “meat-and-potatoes, handshake kind of place” that operated anonymously from its headquarters in downtown DC, says Roman Oben, a 12-year NFL veteran and former union player representative. The players spent just $60,000 on lobbyists in 2006, while NFL owners spent $740,000.

Smith came to the union from Patton Boggs, where he was a litigation partner and chair of the firm’s government-investigations unit. He served on President Obama’s transition team after nearly a decade at the US Attorney’s Office for DC and a stint as counsel to then deputy attorney general Eric Holder.

Under Smith, the players’ lobbying budget has ballooned to $340,000 in the first nine months of the year. Union representatives have met with nearly three-quarters of all members of Congress to share their message that an NFL lockout would mean angry constituents, roughly 150,000 job losses for stadium workers, and collateral damage to local economies. Meanwhile, the players union has hired inside-the-Beltway media strategists to raise public awareness of a potential work stoppage. The goal is to put enough pressure on the league to prevent the lockout.