The Trials and Tribulations of Rudy Giuliani

Mugshot of Rudy Giuliani, photo courtesy of the Fulton County Sheriff’s Office

Two stories leapt out of the news this week on the man once known as “America’s Mayor,” and now better known for his bonkers presser at Four Seasons Total Landscaping. (If you ever need to pull yourself out of a funk, you can relive the moment on TikTok here. I challenge you not to laugh again.)

The first story—the more public one—concerned Giuliani’s loss by way of default judgment in a defamation case brought by election workers Ruby Freeman and her daughter Shaye Moss. The judgment came in the form of a discovery sanction imposed by clearly fed-up District Court Judge Beryl Howell, whose scathing 57-page Memorandum buried Giuliani legally. I’ll explain how badly, and what we can expect next, in greater detail below.

The second story flew a bit under the radar, but it potentially has far wider ramifications. Rolling Stone reported that Jack Smith has been delving into Giuliani’s frequent consumption of alcohol, asking witnesses about whether he was inebriated while working at the White House and advising Trump on or around Election Day and in the weeks to follow.

My first thought was probably similar to how others reacted. Rudy’s a drunk, yeah we know. But then it dawned on me. Rudy is a drunk, and Trump knew it. And that is a whole different ballgame.

Rudy’s trials: Defamation edition

Giuliani is the last defendant standing in a defamation case brought by Freeman and Moss. He had spread some truly despicable lies about the two women, not only falsely accusing them of stuffing ballot boxes and being criminal conspirators, but also falsely implying, through racist tropes, that they were hardcore drug users.

Specifically, before a hearing with Georgia state legislators, Giuliani claimed that Freeman and Moss had hauled fake ballots out of a suitcase from beneath a table in order to commit election fraud. He showed and circulated a heavily edited video which was later roundly and definitively debunked. Despite knowing they were false, he and others, including Trump, continued to level the baseless accusations and spread the false claims.

Giuliani also stated at a state hearing that Freeman and Moss were “passing around USB ports like they were vials of heroin or cocaine.” The January 6 Committee reported that they were in fact sharing some ginger mints.

The false attacks upon Freeman and Moss, and Giuliani’s and Trump’s defamation of their characters, was a form of stochastic terrorism. It drew death threats from MAGA extremists, and the two women felt unsafe going anywhere in public. It upended their lives in a way they could never have imagined, and their ordeal is now front and center in the RICO conspiracy criminal case against 19 defendants, including Giuliani and Trump.

Freeman and Moss sued and achieved a settlement with One American News Network for an undisclosed amount. Giuliani, however, stonewalled the case, refusing to turn over basic discovery for years, while claiming he had lost access to it because the FBI had seized his mobile and other electronic devices.

Giuliani had already conceded, in two separate stipulations, that he had made false statements about Freeman and Moss, even while he continued to assert that his statements were protected under the First Amendment. Judge Howell was less than impressed, however, at his attempt to escape his obligation to produce the demanded discovery, noting that he was an experienced prosecutor who understood his duty to preserve evidence. Of his weak stipulations, she wrote that they “hold more holes than Swiss cheese.” Ultimately, she declared Giuliani liable for “defamation, intentional infliction of emotional distress, civil conspiracy and punitive damage claims.”

Discovery sanctions of this magnitude are rare. And that’s because few litigants ever let it get this bad. Judge Howell arrived at this decision after concluding that Giuliani had paid only “lip service” to his discovery obligations and had failed “to take reasonable steps to preserve or produce” much of anything demanded of him. In fact, as MSNBC legal analyst Lisa Rubin noted, Giuliani ultimately turned over only “193 documents, . . . a single page of communications, blobs of indecipherable data, [and] a sliver of the financial documents required to be produced.”

Judge Howell also had little patience for Giuliani trying to play a victim of the state. “Donning a cloak of victimization may play well on a public stage to certain audiences, but in a court of law this performance has served only to subvert the normal process of discovery in a straightforward defamation case,” the judge wrote.

The case will now proceed to a trial on damages, skipping past liability. There is an open question of how much money Giuliani still has. While he has pleaded poverty, Judge Howell noted that Giuliani was able to get Trump to reimburse him for his electronic legal debts, that he has listed his Manhattan apartment for $6.5 million, and that he traveled on a private plane to report for processing in Fulton County jail just last week.

Rudy’s tribulations: a drunk in the White House

It was no big secret that Giuliani was often drinking while on the job, sometimes excessively. But why are Jack Smith and his investigators interested in the details, particularly as to whether Giuliani was drunk on Election Night and in the weeks to follow? Isn’t this taking things a bit too far, maybe even making them personal? Sure, Rudy has his demons; what’s the big deal?

My own “aha!” moment came as I read the report in Rolling Stone. Smith’s line of inquiry comes down to Trump’s likely defense in the January 6 federal case in D.C. Trump’s lawyers have made it clear that they intend to rely on an “advice of counsel” defense. And that counsel includes Giuliani.

Here’s the thing: For an advice of counsel defense to stick, a defendant needs to satisfy a few key elements. One of them is that the client (here, Trump) needs to have made full disclosure of all the material facts to the lawyer. And that generally requires the lawyer to have actually fully understood what was conveyed.

It’s not hard to see why laying out all the facts to a lawyer blitzed off his ass would fail to qualify here. “I told my lawyer, but he was drunk” is likely not an effective advice of counsel defense.

A client also must also prove that he was acting in good faith by reasonably following that lawyer’s advice. Again, it’s not generally good faith to rely upon the advice of a lawyer whom you know to be drunk. On Election Night, for example, it was an allegedly soused Giuliani who advised Trump to go out and declare victory early, even while everyone else was frantically giving Trump the nix sign. If your drunk counsel advises something like that, while everyone else who is sober in the room pleads with you not to do it, it’s simply not good faith to follow the one drunk lawyer’s advice.

How much Trump knew about Giuliani’s drinking and related mental instability now seems as relevant as what he subjectively thought about the “crazy” theories of Sidney Powell—another one of his supposed counselors. 

In this I see a decent trial narrative forming, one that the jury can grasp easily. All the sane, sober, White House lawyers like Pat Cipollone and Eric Herschmann (“Team Normal”) were telling Trump one thing, while all the drunk, insane, outside lawyers like Rudy Giuliani and Sidney Powell (“Team Crazy”) were telling him another. And what did Trump do? He went with the advice of Team Crazy.

He did so because it fit what he wanted to do—stay in power at all cost. But he knew all along that they were either drunk or crazy, and that they were all in on the conspiracy together. So he can’t effectively claim advice of counsel now as a defense, and it was at a minimum willfully blind or reckless for him to go down any path with them.

These two aspects of Giuliani’s life are emblematic of where he finds himself: in a steep downward spiral, with not only his mounting legal woes but his personal life under heavy scrutiny by judges and prosecutors. (Don’t even get me started about the sexual harassment lawsuit his former assistant has filed.) This doesn’t end well, I would guess, for the man who once graced the cover of Time Magazine.

I’m going with broke, drunk and in jail.