Jon Gruden asked for it, and Jon Gruden definitely is getting it.

After a legal odyssey that somehow staved off the NFL’s obsession to force his five-year-old lawsuit into arbitration controlled by the league, Gruden won the ability to have his claims litigated in open court. Now that the litigation is moving forward, Gruden is drowning in the obligations of the discovery process.

In August, the presiding judge publicly criticized Gruden and his lawyers for “lack of compliance with the rules.” More recently, it got worse for Gruden.

A lot worse.

Michael McCann of Sportico has obtained a transcript of a recent hearing regarding the ongoing efforts of the NFL to secure information to which the league is entitled, under the so-called rules of civil procedure. And the transcript sends an unmistakable message: Judge Joe Hardy seems to suspect that Gruden could be actively hiding evidence that could harm his case.

The current focal point is a phantom BlackBerry device. It existed, and now it doesn’t.

“So did your client lie to you about a BlackBerry?” Judge Hardy said at one point during the hearing.

“It’s not a lie, Your Honor, it’s a mistake,” attorney Adam Hosmer-Henner responded. “And what [Gruden] told me is that he had an old BlackBerry that he couldn’t turn on.”

The judge apparently senses that Gruden’s side is playing a shell game with the BlackBerry device in question.

“Did anybody from your office ever check to see if there was an actual BlackBerry?” Judge Hardy asked Hosmer-Henner.

“Mr. Gruden resides in Florida,” Hosmer-Henner said. “We did not send an individual to rummage around his house to look for a BlackBerry. And what we did do is promptly respond to interrogatory responses providing all this information. With regard to the forensic collection, Mr. Gruden was at an event at the White House last week. He flew back that night in order to allow the forensic examiners selected by the NFL to go through his electronic devices and —"

“So let me interject there, too, because if you can’t tell, this process is frustrating,” Judge Hardy said. “And you, on behalf of your client, keep saying things that seem to indicate, well, Mr. Gruden is super important and super special. And, you know, we should accommodate his schedule. For example, you just mentioned, well, he was at an event at the White House.”

At one point during the hearing, Judge Hardy said this: “We have no reason to trust representations by Mr. Gruden.”

Judge Hardy, per McCann, ordered Gruden to compensate the league for a portion of the attorneys’ fees incurred in connection with the ongoing effort to force him to comply with the rules. That’s an unusual development in any civil case, and it underscores Judge Hardy’s growing frustration with Gruden and his lawyers.

Here’s why it’s a major problem for Gruden. The same judge who has come to the conclusion that the “representations by Mr. Gruden” should not be trusted will be making many key decisions about the merits of Gruden’s case. If it proceeds to trial, Gruden will testify under the supervision of Judge Hardy.

And Gruden, who has a strong will, a quick temper, and a profane vocabulary, will be scrutinized very carefully by a judge who has already decided that he has “no reason to trust representations by Mr. Gruden.”

So, no, it’s not going well for Gruden. And it’s his own fault. At best, he has failed to honor the duty to comply with the rules of the legal process he initiated. At worst — and as the judge undoubtedly suspects — Gruden possibly is trying to hide a device that may contain communications that could hurt, if not kill, his entire case.

On the surface, the idea that someone connected to the NFL weaponized supposedly confidential emails from an unrelated investigation to force Gruden out of his head-coaching job with the Raiders during the 2021 season is troubling. It becomes impossible for Gruden (who is already operating at a disadvantage due to the objectively problematic contents of the emails that were leaked) to prove a violation of applicable legal principles if he creates the impression that he’s not cooperating with the process.

Or, even worse, if he is deliberately and actively trying to conceal other emails and/or text messages.

At this point, it becomes critical for Gruden to do anything and everything he can to regain the trust of the judge. Without that, it’s just a matter of time before Gruden loses his case — and possibly ends up being required to reimburse the NFL for millions of dollars in fees and expenses incurred in defending itself against a case that Gruden seems to not be taking as seriously as he should.