Every night, in the darkening stillness of his luxury apartment on the Upper East Side, Rudy Giuliani puts on a suit and a tie, affixes an American flag lapel pin above his left breast, sits at his desk in his wood-paneled corner library with views over Madison Avenue, stares into a camera, and starts talking.
And then he keeps on talking and talking, delivering, as he has for over a year, hundreds of hours of pure, uncut Rudy at his Rudest. Brad Raffensperger, the Georgia secretary of State whom Donald Trump allegedly tried to coerce into election fraud on his infamous post-election phone call is “a real wussy.” The former intelligence officials who signed a letter warning of Russian interference in the 2020 election were “willing to suck anything they wanted to suck to get ahead.” And Fani Willis, the Fulton County district attorney who is prosecuting both Trump and Giuliani for trying to overturn the 2020 election is “a buffoon.” Hunter Biden, who Giuliani has done more than anyone to torment, is “a traitor” who is “sitting in his closet, contemplating his penis and smoking a crack pipe.” Jill Biden got COVID-19 for a second time because “she has too many holes in her arms” from keeping up with the booster shots, and “you are going to get bacteria in your arms,” presumably from all the holes there.
He has discovered that last refuge of the disgraced in 2023: The vodcast.
America’s Mayor Live is sort of an updated version of the weekly WABC “Live from City Hall … With Rudy Giuliani” he hosted as mayor, where he would spar with his interlocutors over everything from baseball to keeping a ferret as a pet. “Why don’t you seek counseling somewhere, Bob?” he told a caller from Manhattan who asked about ethical troubles dogging members of Giuliani’s inner circle. “I think you could use some help. I can see the direction we’re going in — there are people so upset and so disturbed that they use radios for these sick little attacks on people. I hope you take this in the right spirit, Bob. You should go to a hospital. You should see a psychiatrist.”
There are no such incursions in Giuliani’s current on-air time. The show, going out on YouTube and Rumble, doesn’t allow for call-ins, and nasty comments can be deleted or ignored. It is supposed to be only an hour but often extends into what his team calls “Soccer Time,” by which they mean that it often goes over schedule, sometimes up for another hour.
Each afternoon he appears on WABC, in between appearances on Newsmax TV and dinners with his coterie of admirers, all of it animated by his endless compulsion to just talk. (Though not to me: Giuliani’s team repeatedly blew off interview requests.)
And even though Giuliani is in the headlines on a near daily basis these days, often because of yet another piece of bad news, he scarcely mentions his troubles on his show, preferring instead to rail against the conspiracy against him led by Joe Biden.
It was Biden after all who torpedoed Giuliani’s 2008 presidential ambitions by referring to everything he said as noun-verb-9/11, and Biden’s Justice Department that has made him an unindicted co-conspirator in its election-interference case against Donald Trump. Perhaps most galling of all, before he was even president, it was Biden who attempted to muzzle him. Back in 2019, the Biden campaign sent a letter to the major cable networks, warning them not to have Giuliani on to discuss Ukraine, where he had gone digging up dirt on Joe and Hunter, and Trump’s impeachment because Giuliani was routinely spreading outright lies. They mostly agreed, and after the election, even Fox News stopped having him on.
On this night in particular, Giuliani calls the president “Joseph Robinito, Robi-boo-pee, Robi-dap-ee-doo-boo-pee.”
Then he pauses. “That won’t get him,” he says. “I know how to get him.”
Giuliani is preparing to deliver a devastating nickname for Biden, one that will be picked up by the masses, cripple his presidency, and finally bring about the redemption of Rudy Giuliani’s good name that he has so desperately sought.
The only problem is Giuliani has been riffing on nicknames of various historical mob figures (“Carmine Persico, a.k.a. ‘Junior,’ a.k.a. ‘the Snake’”) and isn’t quite sure how he has now landed on Biden but knows he needs a knockout blow. “Joseph Robinette Biden, a.k.a. …” he says, the mischievous smile rapidly leaving his face as he seems to realize he has no idea how he arrived at this particular rhetorical ledge.
“A.k.a.,” he says, gathering his mental strength.
“A.k.a., ‘the Old Man!’” an apparent reference to the fact that Biden is 80, while Giuliani is still a spry 79.
The number of people watching, or listening over X broadcasts (Giuliani’s team hasn’t yet figured out a way to consistently get the show onto most podcast platforms) is achingly small, usually just a few thousand viewers on YouTube and a few thousand more on Rumble. A spokesman for Giuliani told me that the show is on track to garner Giuliani hundreds of thousands of dollars a year in sponsorship money. That seems unlikely: The only apparent sponsor is Balance of Nature vitamins, which earlier this year agreed to pay $1.1 million to settle false-advertising claims in a suit brought by several Bay Area district attorneys who disputed that the pills had “the nutritional equivalent of over 5 servings of fruits per dose” and that three capsules had as much nutrition as “from eating more than 10 servings of a salad made with 31 different fruits and vegetables.”
At commercial breaks in the middle of his show, Giuliani, sitting in front of a bookshelf lined with biographies of Ronald Reagan, Winston Churchill, and Yogi Berra, tilts back a Balance of Nature bottle and pours the pills into his mouth. When one tumbles off his desk, he says he’ll get it later. “I don’t like wasting,” he says, popping another into his mouth. “Excellent! Excellent! Now I have the energy to keep going.” Take these, he told his audience, “and you will have the energy Trump has.” He also suggested that the pills could replace garlic to boost male virility.
Whatever Balance of Nature pays him, he surely needs the money. As recently as 2016, Giuliani ran a security-consulting business and was the named partner of a major New York law firm; combined with his lobbying and public-speaking appearances cashing in on his 9/11 stardom, his net worth by some estimates was $100 million. He owned six houses and 11 country-club memberships, and according to Andrew Kirtzman’s biography of him, Giuliani: The Rise and Tragic Fall of America’s Mayor, he once threw a fit on a private plane because it was not stocked with cashmere blankets.
That geyser of money dried up just as he was hit with a staggering amount of legal debt.
First, there was the divorce from his third wife, Judith Nathan, that cost him $42,000 a month in alimony. Last year she claimed he owed $260,000 after he skipped multiple payments. (A judge threatened him with jail time after missing a court hearing about the unpaid debts.) Giuliani has also been sued by Hunter Biden over allegedly hacking and disseminating the contents of the First Son’s personal data originally from his laptop. Two Georgia election workers sued him for defamation, winning a judgment to make Giuliani fork over $89,000 in legal fees. (When he didn’t produce financial-related documents for the damages, a judge said Giuliani had committed “continued and flagrant disregard of the court’s orders.”) A former associate filed a lawsuit seeking $10 million for alleged sexual assault and harassment. (As part of the lawsuit, she released audio clips of Giuliani making antisemitic and homophobic remarks.) Dominion Voting Systems is suing him and several others for defamation, seeking $1.3 billion in damages. Smartmatic, another voting-machine company, wants $2.7 billion from Giuliani and Fox News. (Giuilani’s attorney told the judge he was “close to broke” and couldn’t pay for discovery, which Smartmatic called a “dog ate my homework” excuse. A judge sided with Smartmatic.) A Staten Island supermarket employee demands $2 million after he said Giuliani falsely accused him of assault; he tapped Giuliani on the back and said, “What’s up scumbag?” Giuliani has always considered himself a lawyer before all else, yet his law license has been suspended in New York, and he is now at risk of disbarment in Washington, D.C. He faces a tax lien from the IRS for owing more than $500,000 in payments. Finally, his longtime friend and lawyer Robert Costello sued him for $1.4 million in unpaid legal fees.
After that, Giuliani put his apartment on the market for $6.5 million.
If financial ruin weren’t bad enough, the former U.S. Attorney could very well go to prison. In Georgia, he is charged with 13 felonies in a racketeering case for trying to help Trump overturn the 2020 election. In Washington, D.C., he is co-conspirator No. 1 in the federal case against Trump and could be indicted himself later. Worst of all, the one person responsible for his criminal problems is the same person who could bail him out financially, but all Trump has done is host a single fundraiser for Giuliani at his New Jersey country club, a fact that infuriates Giuliani’s longtime allies, some of whom are also close to Trump. “There are street signs named after Donald Trump,” one said. “They’re called One Way.’”
The two have a long, and fraught history, both figures of New York in the 1990s, when Giuliani helped the city’s reputation recover from municipal bankruptcy and Trump helped his own reputation recover from personal bankruptcy, a relationship that culminated in Trump rubbing his face on Rudy’s fake breasts while he was in drag during a skit for the city press corps. Giuliani at first supported Jeb Bush in the 2016 primary before Trump brow-beat him into announcing an endorsement of him, according to Kirtzman. Giuliani then lobbied to be Trump’s secretary of State, and when Trump demurred for any other cabinet post, Giuliani became his personal attorney, from the Mueller investigation to the first impeachment to January 6.
“Everybody wants to impress their boss and thinks that once they do so their boss will like them or give them a promotion or whatever,” said another Giuliani insider. “And it just doesn’t work that way with Trump. Rudy thought he could prove to Trump how invaluable he was, but Trump just wants whoever can give him whatever he wants next.”
Giuliani was abandoned by virtually all of his remaining allies after he spread lies about the 2020 election and found a new crew populated by members of the far-right MAGA base. For a time he was close with fellow Trump acolytes such as attorneys Jenna Ellis and Sidney Powell, who appeared next to him in the infamous melting hair-dye press conference. They have since turned on him and, along with fellow Trump campaign attorney Kenneth Chesebro, copped plea deals in the Georgia case.
Even conversations with some of the most devoted Trumpists reveal a group who view the former mayor with a mixture of condescension and pity. “It is just really hard to watch where he has ended up,” said one conservative activist in New York, who is close to Giuliani. “He was once the shining Republican knight in New York, and now he has been taken by this cast of clowns who are just not serious and seem to not mind that he is destroying his reputation.”
“He had this fear of being alone,” said Kirtzman, whose biography is the definitive account of Giuliani’s time in and after City Hall. “When he was mayor, life in his administration took a pause at 6 p.m. and resumed at a restaurant, and he would always be the last person to leave, the person who would say, ‘Let’s go have one more drink.’ People at City Hall were his family, and they all worshiped him and competed for his approval and he always needed an entourage.” Bernie Kerik, the disgraced former police commissioner, is the only City Hall veteran who remains close to Giuliani.
Maria Ryan, Giuliani’s girlfriend whom he met while still married to Nathan, is a constant presence by his side. So too is Michael Ragusa, an investigator at Rikers Island who briefly ran for City Council before his campaign was accused of forging the signature of a state lawmaker on its petition to get on the ballot. “He’s one of the greatest men I know,” Ragusa said during an impassioned speech to a couple of dozen guests at the Trump-hosted fundraiser at Bedminster, according to an Instagram video. “If he had 50 cents, he’d give you 25; even if he had no money in the bank, and he’s like a father figure to me.”
The fourth wheel in Giuliani’s crew is Ted Goodman, Giuliani’s self-described “political advisor,” who left his former post as the Michigan GOP’s spokesman. He remains largely unknown to most of the old hands of Giulianiworld, even as he often calls the old crew to let them know about Giuliani’s need for more money in his legal defense fund.
With Goodman’s encouragement, Giuliani tried to relaunch his public image with the YouTube show, an attempt to move him past a litany of embarrassments like putting his hands down his pants after being duped by the actress in the Borat sequel. Figuring that if the man had any talent, it was for talking, they put a camera on the guy and let him riff. The first test show was just Giuliani watching a Yankees game and thinking out loud during it; he was soon prompted to go live every night.
Goodman and Ragusa are often heard offscreen during Giuliani’s show, panning the camera close-up and then just as suddenly pulling it back again, although they occasionally pop up onscreen to, for example, retrieve an errant vitamin that has dropped to the floor. They toss out questions occasionally too, questions that, to call them softballs, wouldn’t be doing softballs justice. “Sure is different than how you handled crises throughout your long and storied career, mayor,” one will say off-camera, interrupting a diatribe about Biden or Willis or some other villain that Giuliani has been working himself up over.
The biggest moment in the whole year of doing shows, by far, occurred in June, when Trump called in and Rudy wished him “Happy birthday.” The conversation lasted just a shade under three minutes and consisted of Giuliani holding his iPhone up to the microphone so that Trump could be heard. Introducing, “our past and future president,” Giuliani told his guest that “there is no need to even tell us that you are innocent — we know you are.”
“Well, Rudy I love your audience too,” Trump responded, his voice distantly coming from an iPhone. “And you are a fantastic guy … And you asked me to call in, and I always call in for you. I just want to say hello to your audience,” before talking about his poll numbers.
“We admire you so much, Mr. President,” Giuliani said before stabbing his index finger at his phone to hang up after Trump had ended the call.
“So that’s a good way to start a show, don’t you think Ted?” Giuliani said when he put the phone down. “What do you think, Ted, you think we could start every show that way?”
“I think so, mayor, and of course, you have enjoyed a long, long friendship with the president, and he told us earlier that he’d call, and he called Right! At! Eight!”
“He called right at eight o’clock!” Giuliani responded, before digressing into the former president’s remarkable ability to be punctual.
Despite the tumult of brutal headlines, multiple lawsuits, and cross-country court appearances, Giuliani hasn’t missed a single episode of America’s Mayor Live since it began last year. Whether he is on vacation in New England, or at Trump’s Mar-a-Lago estate, he sets up somewhere with a camera and a microphone and goes live. After Giuliani surrendered to authorities in Atlanta and got his mugshot taken, he recorded an episode at Teterboro Airport almost the moment his plane touched down. As he loses money, friends, and what little remains of his reputation, at least he has this. Night after night, surrounded by people who work for him and still love him, baying to an audience of almost nothing. No matter where he is located, behind a microphone, Rudy Giuliani is home.
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