It hasn't been an easy selection process, and numerous challenges still lay ahead.
In the shadow of looming collective bargaining talks threatening to end the NFL's long era of labor peace, amid an economic meltdown strangling the nation, and dealing with revolts from bitter retired players, members of North America's most powerful sports union are traveling to Maui to begin plotting a new course in the headwinds of an uncertain future.
Some seven months after Upshaw's death, the NFLPA is expected to finally select a new executive director in a vote scheduled for Sunday. By Monday morning, the union's fourth leader in its 41-year history will face the daunting task of uniting ranks left divided by what's been called a "corrosive" search process that has the potential to weaken the NFLPA and shift the balance of power fully to NFL owners.
"The guy's got big shoes to fill," NFLPA president and Tennessee Titans center Kevin Mawae told The Associated Press. "The next executive director is going to determine the course of the NFL over the next several years. ... So whoever that guy is, he's got a bunch of different fronts that he's got to fight."
There are four candidates for the 32 player representatives -- one for each team -- to pick from. A simple majority of the representatives in attendance decides the winner.
Two candidates are former NFLPA presidents, Troy Vincent and Trace Armstrong. Then there's two attorneys: DeMaurice Smith, an NFL outsider who has no labor law experience but has ties to President Barack Obama and worked with new attorney general Eric Holder; and David Cornwell, who has represented both the union and the NFL.
Vincent is still considered the front-runner, even though he has been the target of a series of mostly anonymous allegations that have raised questions about his character and business background. Despite attempts to remove him from contention, Vincent had the backing of seven of 10 union executive members last month to remain a finalist.
The attacks on Vincent and numerous leaks in what was supposed to be a closed search has brought negative publicity to the union, and raised concerns among its members.
"It's made us look incompetent," Buffalo Bills safety and alternate union representative George Wilson said. "As a union, it makes all of us look bad when it seems we're not capable of handling the business in the proper manner."
Titans player rep and linebacker David Thornton remained confident despite the fractious search process.
"Everything that's happened in the process, you don't know what's true, the hearsay," Thornton said. "The bottom line is this, we have (four) guys, all are great men. All are fully capable of leading this union. But it will only be one. And we want the best guy to lead us into the next phase of football. All the other things now, really don't matter."
Cornwell described the search process as "corrosive" and "destructive" in a letter to Mawae last month. Cornwell was eliminated as a candidate in January, but re-emerged last week after receiving written support from three NFLPA representatives.
Armstrong's ties to Tom Condon, one of the NFL's most influential agents, also have been questioned. Condon and Armstrong both work as agents for Creative Artists Agency. Condon's role in the union has been questioned because he previously represented Upshaw and is a member of the union's retired players committee, which has come under attack for failing to address former players' needs.
Armstrong declined to be drawn into comparisons with Condon, but noted he has an extensive background in union matters -- he was part of three contract negotiations with the NFL and was also a union member when the NFLPA decertified in 1989 and recertified a few years later.
"People have kind of portrayed me as an extension of the past or a status-quo candidate. I'd just like to say that Gene and I disagreed on a lot of issues," Armstrong said. "Sure we disagreed, but we disagreed privately. And at the end of the day, we went forward together and that was critical for the health of the organization."
Armstrong declined to discuss his platform publicly, except to say that he would ask the league open its financial books and show reasons why it wants a new collective bargaining agreement.
"I would say that the league has called us partners. And I would say over the last 16 years we've had a good relationship," Armstrong said. "But partners share information. And if you're telling me things, you're struggling, I understand. But show me the information."
The new negotiations were prompted after the NFL opted out of the CBA last year, arguing that the current agreement is too favorable for players, who get about 60 percent of applicable revenues. The NFLPA countered, citing a union-commissioned study showed the average value of the teams has grown from $288 million to $1.04 billion over 10 years, an increase of about 14 percent a year.
Though the NFL will continue operating through the next two seasons, without a new deal there is a possibility for labor strife in 2011.
Another unresolved issue is addressing the rift that's grown between the union and its retired players, some of whom feel they've been disenfranchised. A host of former stars, including Pro Football Hall of Fame members Mike Ditka, Green Bay's Herb Adderley and Buffalo's Joe DeLamielleure have been increasingly critical of the union over its health benefits and pension plan, which pays some retired players only hundreds of dollars a month.
Adderley won a lawsuit against the union last year when a federal judge ordered the NFLPA to pay $28.1 million to retired players after finding the union failed to properly market their images. The union appealed the ruling last month.
Retired players are threatening further legal action, and are lobbying Congress to force legislation on the NFLPA to increase pensions and benefits.
Both Vincent and Cornwell described healing the rift as important a priority as labor talks.
"There is no CBA if you don't get the house straight," Vincent said.
Cornwell proposes creating a new senior union executive position of special adviser for retired players.
Retired linebacker Bob Grant was skeptical that a new executive director will enact change.
"Some of us feel that it could make a difference, but most of us feel that it will make absolutely no difference at all," Grant said. "As far as we're concerned, we don't have anyone there who's going to do anything more than pay a little lip service to us."
Clouding the union's direction further is an unraveling economy, which has the potential to affect NFL revenues, from marketing, TV rights and attendance.
"It's funny, it seems like the economy is always the issue," said Redskins player rep and receiver James Thrash. "The big thing, No. 1 from a player's standpoint, is we just need a leader."
After seven months and a difficult search, the union will finally have that.
"I don't know what's going to happen overnight," Mawae said. "I think the next guy, whoever it's going to be, will have to prove himself."
