Jon Gruden’s pre-2025 emails are missing, attorneys say in his suit against NFL

Former Las Vegas Raiders coach Jon Gruden’s lawsuit against the NFL has become mired in what the league sees as discovery problems, including the disappearance of his pre-2025 emails, court records show.

Now, his trial, scheduled for May 2027 after years of litigation, will likely be delayed.

District Judge Joe Hardy said at a Thursday hearing that he was inclined to extend the discovery period and postpone the trial, which was scheduled to start in May 2027. Discovery is the process by which opposing parties share information to prepare for trial.

Gruden filed his lawsuit in 2021 against the NFL and NFL Commissioner Roger Goodell, arguing that the league leaked emails he wrote with racist, misogynistic and anti-LGBTQ language and pushed for the Raiders to fire him. He resigned from his coaching role after news reports emerged about the emails, which the NFL has denied leaking.

Judge: ‘Lack of compliance’

Gruden’s attorneys insist that he is complying with discovery. NFL attorneys want him to be held in contempt for what they perceive as his violations of a discovery order.

At recent hearings, Hardy’s patience with Gruden seems to be wearing thin.

The judge — who has criticized both sides at different points — noted Thursday that Gruden initiated the case and that discovery is proceeding at his request, over the objection of the NFL. Earlier this month, he awarded the NFL some legal fees and costs related to discovery.

“I remain concerned with Gruden’s, Gruden’s side’s delays and lack of cooperation, lack of compliance with the rules,” he said at an August hearing.

“Mr. Gruden is the plaintiff here. And he has not been in full compliance with discovery rules,” the judge said at a hearing last month, a transcript shows. “We’re here because of that.”

Gruden attorney Adam Hosmer-Henner disagreed at the the time that his client had failed to comply.

Missing emails

A lawyer for Gruden disclosed in late August that Gruden’s email account contains no emails from before 2025, according to a September status report signed by attorneys for Gruden and the NFL.

“Mr. Gruden’s counsel stated that it ‘appears likely’ the emails have been deleted but that Mr. Gruden told him that he did not believe he had affirmatively deleted any messages and did not know why or how the emails were not available,” the report said.

The former coach’s lawyers have argued that he has mostly completed producing documents and that the “unexpectedly unavailable” personal emails would not be central to the case, because Gruden had a Raiders email account until he was terminated.

The NFL sees the situation differently.

League attorneys argue that Gruden has violated his discovery obligations and that “key evidence has been lost or destroyed.” The NFL has said in court papers that Gruden’s texts before 2021 are also largely missing and that only 96 text threads begin in 2021, compared to about 2,000 in 2025 and 2026.

“This case is about October 2021: the month Mr. Gruden’s emails were published, the month he resigned from the Raiders, and the month he claims to have lost more than $150 million in opportunities,” NFL attorneys wrote in a recent filing. “Yet every email he sent or received before 2025 is gone, and his counsel has acknowledged it ‘appears likely’ they were deleted.”

Hosmer-Henner said in court Thursday that his firm has produced records for NFL forensic examiners. The NFL will be able to image and analyze documents to see if Gmail records can be recovered, he said, later adding that there should be limits on what the league can search.

He indicated that Gruden’s side would also like to know what happened to the missing records.

“Our position is yes, we tried to cooperate as far as we could and truly, having multiple people come to Mr. Gruden’s office, spend a day there downloading all the information, looking at his phone, his Gmail account and other devices,” he said.

NFL attorneys said in a filing that Gruden failed to timely facilitate an export of his Gmail account, delaying the NFL’s investigation into whether the emails can be retrieved.

Gruden attorney complains about Goodell

In a Monday filing, Hosmer-Henner complained about the NFL’s discovery conduct, including that the league had failed to produce emails or text messages from Goodell.

He also characterized as “inadequate and evasive” a response from Goodell to a discovery query asking him to admit that he knew who provided documents or communications concerning Gruden to The Wall Street Journal and The New York Times.

According to Hosmer-Henner’s filing, Goodell objected to the form of the inquiry, but said, “Commissioner Goodell construes this Request as asking him to admit that someone at the NFL provided to the Wall Street Journal or the New York Times copies or the contents of emails between Gruden and Bruce Allen that were quoted or referenced in the WSJ Article or the NY Times Article. So construed, Commissioner Goodell denies the Request.”

NFL attorney Laura O’Boyle said at the Thursday hearing that her side has produced almost 10,000 documents along with responses.

She said she spoke with Hosmer-Henner about discovery on Tuesday.

“I told him that we would be producing documents from Commissioner Goodell,” she told the judge. “We are going to produce emails and text messages that are responsive from him and from other custodians.”

She also argued that the disputed query from Gruden’s side was “impossible to answer” because it was not time-constrained or specific. “It is asking effectively: at any point in time in the history of the world does the NFL know if someone provided something about Mr. Gruden to two news organizations,” she said.

O’Boyle added: “What it feels like to us, your honor, is that Mr. Gruden tried to come up with a bunch of issues at the last minute, before he attempted to confer with us about anything, to try to deflect attention away from what he’s doing.”

She wants the NFL’s discovery obligations to be paused until Gruden complies.

Hardy said Thursday that he would order the litigants to meet about the possibility of appointing a special master.

Contact Noble Brigham at [email protected].