A battle Jon Gruden started against the NFL in 2021 still rages on, but the tides are turning against him by his own doing.

In 2021, Gruden alleged that the league had leaked confidential e-mails with the purpose of removing him as the head coach of the Las Vegas Raiders. In a Case Conference Report his team filed this February, Gruden sought more than $150 million in compensation for “loss of his employment, interference with future employment opportunities, loss of contract value, loss of sponsorships, reputational damage, costs, expert fees, and attorney fees incurred as a result of this dispute.”

The league pushed back in July, saying the documents Gruden had provided as evidence weren’t sufficient, and that they couldn’t get any answers from Gruden’s camp at times. To get to the bottom of this, District Judge Joe Hardy gave Gruden seven days to provide documents and talk to interrogators. But that deadline’s long past, and Judge Hardy isn’t happy with the way things have been handled.

“I remain concerned with Gruden’s, Gruden’s side’s delays and lack of cooperation, lack of compliance with the rules,” Judge Hardy said on Monday, August 10th, per Noble Brigham of the Las Vegas Review-Journal.

Per Brigham, Gruden’s attorney, Adam Hosmer-Henner, has “previously accused the league of stall tactics.” But with the shoe now on the other foot, NFL lawyers have gone on the offensive.

“Discovery is the process by which the parties test claims like his against the evidence,” the NFL attorneys wrote in court papers, per Brigham. “A plaintiff genuinely confident in his allegations produces his documents promptly and answers the questions put to him truthfully. Gruden has done neither.”

With the delay now coming from Gruden’s camp, Judge Joe Hardy’s statement has put Gruden on the spot.

“No explanation was proffered by Gruden’s side that would address the court’s concern about the delays, particularly in light of months ago, when I said, in Gruden’s favor and against the NFL’s position, we’re going forward,” Judge Hardy said. “Gruden understandably at least represented to me that their side wanted to proceed expeditiously and has done the opposite of that.”

Both sides are still in a deadlock. Gruden’s camp is pushing back “saying the league was making overly broad requests for records in an attempt to embarrass Gruden,” per Brigham. They are also pointing to the league’s refusal of a protective order that would mark the “disclosed documents confidential.”

“[NFL attorney Mark] Hutchinson said Gruden’s side never said their disclosures were deficient or demanded a protective order before providing records,” Writes Brigham. “They also did not serve a document request on the NFL, the league’s lawyers said, adding that there were discussions about a protective order, which stalled based on one proposed change.

“Hosmer-Henner told the judge his side did respond to discovery requests and produce nonconfidential documents, but also took into account an ongoing appeal of a prior ruling. The Judge was skeptical.”

The $150 million lawsuit still has no resolution, but now has a district judge calling out Gruden’s camp.

“You’re saying you’re proceeding expeditiously, but clearly you’re not,” Judge Joe Hardy said.