Several of the emails that led to Jon Gruden's resignation as Las Vegas Raiders head coach were submitted to a U.S. District Court in June by attorneys representing Washington Football Team owner Daniel Snyder.

Months before the emails were leaked, Snyder's lawyers used them as exhibits in a legal battle involving former team executive Bruce Allen, who was fired in 2019. Allen is the recipient of several of the damning emails cited in Monday's New York Times report that ultimately led to Gruden's ouster.

Snyder's lawyers attached the emails to a motion seeking to compel Allen to produce discovery as part of Snyder's defamation lawsuit against an Indian media outlet that falsely linked him to sex trafficking and disgraced late financier and convicted sex offender Jeffrey Epstein.

The filings — first reported by the Los Angeles Times, and later obtained by Yahoo Sports — also include communications between Allen and media members, including ESPN's Adam Schefter. They provide a window into reporting tactics behind the NFL insider's work.

Snyder sought to connect Allen to false reports

The legal battle is mostly, though not entirely, unconnected to the Gruden saga. Snyder sued New Delhi-based Media Entertainment Arts WorldWide (MEAWW) in August 2020 seeking $10 million over the false claims. In subsequent filings, he effectively accused the team's minority owners and a former team employee of conspiring to leak damaging information to the press.

Those allegations mentioned MEAWW, but also the Washington Post, which a month earlier had published an exposé of sexual harassment and workplace misconduct within the franchise. The Post report led to the NFL's investigation of the team, which ultimately led to Gruden's emails surfacing.

This past April, Snyder added to his allegations, and filed a motion naming Allen as a potential source. Two months later, as part of an effort to force Allen to turn over evidence, Snyder's lawyers filed the emails to show that Allen had close relationships with media members.

(Allen denied the allegations, and the case has since been dismissed.)

Gruden's emails

Gruden, working for ESPN at the time, was one of those media members. His name is redacted in the court filings, but the homophobic and misogynistic emails match those described by the New York Times on Monday.

In one, the "Redacted - ESPN Personality" rages to Allen about a "clueless anti football p***y" — which the Times reported was a reference to NFL commissioner Roger Goodell.

In another, he says Goodell shouldn't tell teams to "draft queers" — a reference to the Rams' 2014 selection of openly gay defensive lineman Michael Sam.

In another, sent directly to Allen on Aug. 28, 2016, he references an NFL statement one day earlier, in response to Colin Kaepernick's initial protests of police brutality.

"They suspend people for taking amino acids they should cut this f**k," the "Redacted - ESPN Personality" wrote.

Allen responded, in part: "I've expressed my OUTRAGE."

The "ESPN Personality" then wrote back: "Good for you."

Allen also criticizes protests

In a later email unrelated to Gruden, from 2018, Allen told conservative talk show host Mark Levin that, "remember 90%+ of NFL players have never considered kneeling. The 10% of the players and owners are the issue (see [Eagles owner] Jeff Lurie & 49ers owner)."

"Good points, will hit some of this now," Levin responded, presumably referring to his show.

"Thanks," Allen wrote back. "This is so ridiculous it's embarrasing."

Schefter sent ESPN story to Allen for review

Perhaps the most revelatory emails in the filing don't pertain to Gruden. Exhibit 1 is a 2011 exchange between Allen and Schefter, during negotiations between players and owners over a new collective bargaining agreement. A little after midnight on July 11, Schefter sent Allen an entire draft of a story that would be published later that day.

"Please let me know if you see anything that should be added, changed, tweaked," Schefter wrote to Allen. "Thanks, Mr. Editor, for that and the trust. Plan to file this to espn about 6 am."

Allen responded seven minutes later that it was "good stuff," and that there were "a few other issues" in the CBA "still being debated."

"That's fine," Schefter replied. "But as long as the meat of it is correct, which I believe it is, all good. Going to bed. Talk tomorrow, Bruce."

ESPN, when notified of the exchange, told the LA Times in a statement: “Without sharing all the specifics of the reporter’s process for a story from 10 years ago during the NFL lockout, we believe that nothing is more important to Adam and ESPN than providing fans the most accurate, fair and complete story.”

Other emails show Schefter and Allen exchanging information, in correspondence that illustrates a more standard reporter-source relationship. In 2017, for example, prominent agent Drew Rosenhaus, who represented then-49ers linebacker NaVorro Bowman, sent an email titled: "NAVORRO BOWMAN is available in a trade. Please call me if interested. I have permission from the Niners to discuss."

Allen forwarded the email the Schefter. "Love this!" Schefter responded. "That's unlike you, sharing something good. I will use Sunday morning! I am grateful and appreciative. Thank you!!!"

The following day, Schefter reported that the 49ers were "shopping" Bowman, "and there are teams interested, sources tell ESPN. His time in SF could soon come to an end."

Some 90 minutes later, the Niners released Bowman.

Other emails show Allen communicating with reporters from the Washington Post and other outlets. Reporters names were redacted in the initial filing in mid-June. In late June, Snyder's attorney filed amended exhibits that were less-redacted — though only the names of reports, and not the names of football people, were uncovered.

Snyder, meanwhile, is under increased scrutiny as the NFL is facing calls to release all of the reported 650,000 emails that were part of the probe into the Washington Football Team.