The National Football League has a new concern around its investigation of the 650,000 emails that have already resulted in Las Vegas Raiders coach Jon Gruden’s resignation: The league’s general counsel is a participant in email threads with the former Washington Football Team executive whose inbox is under scrutiny.  

Jeff Pash, who has worked for the league for over two decades, was a frequent email correspondent with Bruce Allen, the former Washington Football Team general manager and president. 

In...

The National Football League has a new concern around its investigation of the 650,000 emails that have already resulted in Las Vegas Raiders coach Jon Gruden’s resignation: The league’s general counsel is a participant in email threads with the former Washington Football Team executive whose inbox is under scrutiny.  

Jeff Pash, who has worked for the league for over two decades, was a frequent email correspondent with Bruce Allen, the former Washington Football Team general manager and president. 

In the emails, Pash and Allen discussed topics including politics, league investigations such as the Patriots Deflategate scandal, NFL officiating and problems within the team’s cheerleader squad. They casually discussed issues such as players voting and the team’s former name, the Redskins, which was a lightning rod for controversy.   

“Communication between league office employees and club executives occurs on a daily basis,” said Jeff Miller, the NFL’s executive vice president of communications. “Jeff Pash is a respected and high-character NFL executive. Any effort to portray these emails as inappropriate is either misleading or patently false.” 

People familiar with the matter previously said that, other than Gruden, no other league official’s communications were flagged as meriting potential of discipline. 

Allen’s inbox included the inflammatory emails from Gruden—including racist and antigay comments—that led to Gruden’s resignation in the days since The Wall Street Journal reported that the Las Vegas Raiders coach used a racial trope to describe NFLPA executive director DeMaurice Smith. In a 2011 email to Allen, Gruden wrote that, “Dumboriss Smith has lips the size of michellin tires.” 

That email was just one of more than 650,000 the league was examining after they surfaced as part of an independent investigation of the workplace culture of the Washington Football Team.

The New York Times subsequently reported, and the Journal confirmed, that Gruden used anti gay and other offensive language in other emails. Gruden resigned on Monday. 

In Pash’s emails reviewed by The Wall Street Journal, he was not a participant on the email chains that led to Gruden’s departure.

In one 2016 email exchange, after a Democratic woman was hired as the NFL’s new vice president of public policy and government affairs, Allen wrote to Pash: “Curious — is there a rule against hiring Libertarians, Independents or even a Republican? We have the Rooney Rule …. So I’m going to propose a Lincoln Rule at the next meeting.” 

“No, but it can sometimes look that way!” Pash replied. 

League officials said the exchange reflected the NFL’s hiring of a number of people who had come from the Democratic party over the years in that role. The current person in that role came from working on the Republican side of the aisle. 

In 2018, Allen told Pash that if NFL rules allowed employees to gamble, he’d bet that less than 1% of players voted in the primaries. “Maybe even take the under,” Pash replied. 

Pash’s frequent correspondence with Allen raises questions about what his role was in a pair of investigations—one into the Washington Football Team’s workplace culture and one into Allen’s emails. Pash’s emails suggest a close relationship with Allen, who was second only to Snyder among the team’s brass during years the workplace investigation covered.

If Pash has a role in the email investigation, too, it would raise questions given his prominence in the investigation’s evidence.  

League officials reiterated that the Washington Football Team workplace investigation was run by an outside lawyer, Beth Wilkinson. The point people on the email investigation were deputy general counsel Janet Nova and Lisa Friel, the NFL’s special counsel for investigations, who reported to commissioner Roger Goodell on the matter. Nova and Friel were also the key people who reported to Goodell regarding the Washington Football Team, the officials said. Pash, as the league’s top lawyer, was not siloed off from those investigations—his advice and counsel were still sought, the officials said. 

“I have worked closely with Jeff Pash for many years,” New York Giants owner John Mara said. “He is a principled leader who has always served the league with integrity.”

Two other owners, the Chicago Bears’ George McCaskey and the Arizona Cardinals’ Michael Bidwill, issued similar statements strongly touting Pash’s integrity and character.

The pair discussed some of the league’s most sensitive issues where Pash had a key role. In a 2015 discussion, when Tom Brady and the New England Patriots were accused of violating NFL rules by deflating footballs, Allen suggested the referees and umpires should be able to control the balls and ensure they are legal. Pash, in his reply, said it would be a lot to ask to tell small differences in air pressure just by feel. 

“Seems to me that it would be easier if the teams just refrained from tampering with the balls after the ref approves them,” Pash wrote. 

League officials, after first learning of the giant email trove during the workplace investigation, found some of them troubling. But it was determined that they were outside the scope of the original probe of the Washington Football Team. So while the league wrapped up the Washington investigation—and fined the team a record $10 million—it launched a separate investigation of the emails. 

Commissioner Roger Goodell was briefed on the investigation’s findings last week, and the team had been planning to discuss Gruden’s emails with the Raiders at a yet-to-be-scheduled meeting. Those plans were disrupted, however, when The Journal initially reported on Gruden’s email last Friday. Gruden coached his team’s game Sunday before resigning a day later under the additional pressure. 

Those emails raised questions about who else would surface in this trove of emails that spanned years inside the inbox of Allen, who was Washington’s top executive for  a decade until he was fired in 2019. 

The investigation into the Washington Football Team was launched in 2020 after the Washington Post reported 15 women experienced sexual or verbal abuse while working for the club. It later emerged team owner Dan Snyder had at least one confidential settlement, and he denied wrongdoing in a pair of incidents involving him. Roger Goodell, after the investigation led by attorney Beth Wilkinson was done, concluded that the team’s workplace environment was highly unprofessional. The league did not report specifics, however, and said that it received only oral reports instead of a written one. 

Write to Andrew Beaton at andrew.beaton@wsj.com