Rudy Giuliani’s most embarrassing moments

A crime-busting prosecutor who brought down the mob. The tough-talking mayor who cleaned up the mean streets of New York City and demonstrated what leadership looked like in the wake of the 9/11 terror attacks. Both of those sentences aptly describe Rudy Giuliani, former U.S. Attorney for the Southern District of New York and two-term mayor of NYC. 

However, when his obituary is written, all of those accolades are almost certain to be trumped, literally and figuratively, by his subsequent role as personal lawyer to President Donald Trump. As Trump’s attorney, Giuliani has proven there’s no conspiracy theory too wacky to embrace, no behavior too debasing, and no line he wouldn’t cross when attempting to prove the 2020 U.S. presidential election was fraudulent — all without producing any actionable evidence, as of this writing.

As he racked up court loss after court loss in his fruitless attempts to overturn the election results in states that Trump lost (the ones he won, apparently, were miraculously fraud-free), Giuliani careened from one embarrassing public debacle to the next. Read on to discover some of Rudy Giuliani’s most embarrassing moments. 

Yes, Rudy Giuliani actually married his cousin

When Rudy Giuliani embarked on his failed presidential run in 2007, The Smoking Gun uncovered a 450-page report commissioned ahead of his 1993 election as mayor of New York City. The most eyebrow-raising part of the report highlighted the “weirdness factor” in Giuliani’s 14-year first marriage. That was because Giuliani’s first wife, Regina Peruggi, was his second cousin, daughter of the first cousin of his father.

As The New York Times reported, the marriage was “annulled on the grounds that they failed to seek a church dispensation” allowing the cousins to marry. According to Politifact, Giuliani had alternately described he and his ex-wife as “second cousins once removed” and “third cousins.”

The report cited by The Smoking Gun also pointed out some rather glaring inconsistencies in public statements that Giuliani had made about his marriages. “When asked about his personal life, Giuliani gives a wide array of conflicting answers,” noted the campaign report. “All of this brings the soundness of his judgement into question — and the veracity of his answers.”

Rudy Giuliani's marriages all ended in scandal

Rudy Giuilani’s personal life has been colorful, to say the least. This has definitely been the case in his three failed marriages, all of which led him to become engulfed in scandal. While annulling one’s first marriage due to being married to a blood relative would be controversial enough, Giuliani’s next two marriages served up even more tabloid fodder.

As New York magazine’s The Cut recalled, Giuliani married Donna Hanover in 1984. In 2000, Giulani held a press conference to announce his separation from Hanover — who learned about her separation from that very press conference. In the same press conference, he bizarrely referenced his “very good friend” Judith Nathan, with whom he was widely speculated to have already begun dating. Hanover responded by holding her own press conference a few hours later, accusing Giuliani of having an affair with former staffer Cristyne Lategano-Nicholas, an accusation that both Giuliani and Lategano-Nicholas both denied. Giuliani subsequently filed divorce papers, while Hanover was granted a temporary restraining order preventing Nathan from visiting the NYC mayor’s official residence, Gracie Mansion.

After the divorce was finalized, Giuliani married Nathan in 2003. That marriage ended in 2019 amidst rumors that, once again, Giuliani was cheating. According to a report in Page Six, Nathan filed for divorce in April 2018.

His wife blabbed to the media about his scandalous affair

As Rudy Giuliani’s marriage to Judith Nathan crashed and burned, Page Six quoted a source claiming Giuliani had boasted of an affair with a woman who had “big boobs.” This led to speculation that Giuliani’s married mistress was Maria Ryan, a hospital administrator from New Hampshire. Giuliani responded by blasting the rumor as “totally false,” telling Page Six that “whoever told you that is a liar.” Giuliani also denied cheating on his wife.

However, Nathan said it was Giuliani who was the liar. “My husband’s denial of the affair with the married Mrs. Ryan is as false as his claim that we were separated when he took up with her,” she told Page Six

The ensuing divorce was described by The New York Times as “ugly,” with the legal proceedings serving to publicly air all manner of dirty laundry. Among the information detailed in the court case was Giuliani’s extravagant splurges, with Nathan alleging he spent “$7,131 on fountain pens and $12,012 on cigars.” Said the judge presiding over the case, “It is beyond me why either party in this case would have an interest in having all of this done publicly.”

Boozy interviews and unfortunate butt-dialling

In 2018, rumors emerged that Rudy Giuliani was hitting the bottle a bit too hard. As a “friend” speaking with New York magazine revealed, “I’ve seen [Giuliani] drink more in the past two years than I’d seen him drink in the past twenty.” Giuliani fired back in an interview with Politico., refuting an allegation that he was passed over for a cabinet position in the Trump administration, and insisting, “I’m not drinking for lunch. I may have a drink for dinner. I like to drink with cigars.”

A 2019 feature in New York magazine, however, detailed a lunch meeting with Giuliani, which included him downing two Bloody Marys and toppling against a wall while walking down a ramp. He denied rumors of excessive boozing, but admitted, “I love scotch. I can’t help it… I’m a partyer.”

Meanwhile, Giuliani also developed a reputation for “butt-dialing” reporters, accidentally ringing up journalists without realizing they were listening in on his conversations. This took place in October 2019 when he accidentally called an NBC News reporter, with the call — a conversation involving a deal in Bahrain — going to voicemail. As HuffPost reported, this wasn’t an isolated incident, with numerous reporters chiming in to share their stories of receiving a Giuliani butt-dial.

The Ukraine extortion debacle that led to Trump's impeachment

As the 2020 presidential election loomed, Rudy Giuliani (in his capacity as personal attorney to President Donald Trump) embarked on a magical mystery tour of Eastern Europe — specifically Ukraine, to investigate widely debunked claims that Joe Biden (then seen as the frontrunner to be Trump’s eventual opponent), and son Hunter, were involved in shady dealings.

It all blew up in Giuliani’s face when a whistleblower claimed Trump was deliberately withholding hundreds of millions in desperately needed aid while pressuring recently elected Ukrainian President Volodymyr Zelensky to investigate the Bidens, during a phone call on which Giuliani was named several times. That call directly led Trump to become the third president in America’s history to be impeached. 

When news of the whistleblower’s allegations first broke, Giuliani was reportedly apoplectic. “It is impossible that the whistleblower is a hero and I’m not. And I will be the hero!” Giuliani declared to The Atlantic. “These morons — when this is over, I will be the hero.” In response to Giluliani’s rant, a “senior White House official” told The Atlantic that the “entire thing” was the result of “Rudy putting s**t in Trump’s head,” while a “senior House Republican aide” derided Giuliani as a “moron.”

Rudy Giuliani's shady associates were arrested shortly after meeting with him

In fall 2019, Rudy Giuliani was heavily involved in digging up Ukrainian dirt on Joe Biden, which led him to hook up with Ukrainian-born U.S. citizens Igor Fruman (pictured above left) and Lev Parnas (right). In October, the pair was arrested while trying to exit the country. According to CBC News, the Fruman and Parnas were charged with “conspiracy, making false statements to the Federal Election Commission and falsification of records,” and were described as having “key roles in Giuliani’s efforts” to get Ukrainian officials to launch an investigation into the Bidens, reportedly at the behest of the President Donald Trump.

While Giuliani initially attempted to distance himself from the two, that became more difficult when numerous photos of Giuliani and Parnas together later emerged. After his arrest, Parnas appeared ready to tell all when he appeared on Rachel Maddow’s MSNBC show and claimed that Trump “knew exactly what was going on.” Parnas also alleged that the president wouldn’t be satisfied with “a corruption announcement, it [had] to be about Joe Biden and Hunter Biden and Burisma” (via The Hill). Giulani later claimed he’d been “misled” by his arrested associates.

The Hunter Biden laptop thing fell totally flat

Leading up to the 2020 presidential election, Rudy Giuliani’s efforts to find dirt on Joe Biden coalesced into a dubious story in the New York Post that stretched the concept of plausibility to the limit. The twisty tale began when someone who may have been Hunter Biden dropped off some waterlogged laptops at a Delaware computer repair shop.

When they weren’t retrieved, the shop’s legally blind owner went through the hard drives and uncovered some unverified emails that allegedly indicated a convoluted plot to enrich the former vice president. As NPR pointed out, the story was “marked more by red flags than investigative rigor.” Meanwhile, it sure appeared that Giuliani got played by Russian intelligence agents; The Washington Post reported that U.S. intelligence officials warned that Russian operatives were seeking to provide Giuliani with disinformation to use against the Bidens, while NBC News reported the FBI was investigating whether the laptop story originated in the Kremlin and not a Delaware repair shop.

The story proved to be so convoluted and nonsensical that it could barely be understood, but perhaps the final nail in its coffin came when Anthony Bobulinski, a former Hunter Biden associate, attempted to verify it, providing his own claims and documentation. The Wall Street Journal examined Bobulinski’s claims and found “no role for Joe Biden” in whatever it was Hunter actually had going on. And so, the tool intended to inflict political damage, Giuliani’s laptop scandal was a massive flop.

Borat duped Rudy Giuliani big time

As Rudy Giuliani frantically flailed trying to get some traction for his Hunter Biden laptop story, he wound up making a movie cameo that was as unexpected as it was hilarious. In the sequel to Sacha Baron Cohen’s mockumentary Borat, Giuliani is interviewed in a hotel suite by actress Maria Bakalova, playing the 15-year-old daughter Cohen’s titular Borat. She leads Giuliani, flirting shamelessly (“My dear,” he calls her repeatedly), into an adjoining hotel room outfitted with hidden cameras. Suddenly, Giuliani lies back on the bed and jams his hand into his pants, an indelible movie moment as creepy as anything Dennis Hopper did in Blue Velvet. Just then, Borat crashes in to put the kibosh on whatever was about to happen. “She 15!” Borat yells at Giuliani. “She too old for you!”

Giuliani defended himself via Twitter thread, calling the hidden-camera video “a complete fabrication” and claiming he was merely “tucking in [his] shirt after taking off the recording equipment.” He even boldly claimed, “This is an effort to blunt my relentless exposure of the criminality and depravity of Joe Biden and his entire family.” 

Cohen responded, in character as Borat. “I here to defend America’s mayor, Rudolph Giuliani,” he said in a video he tweeted. “What was an innocent sexy-time encounter between a consenting man and my 15-year-old daughter has been turned into something disgusting by fake news media.”

The Four Seasons Total Landscaping press conference debacle

If ever there was a metaphor for Rudy Giuliani’s inept attempts to prove nonexistent voter fraud and invalidate an election, it was his widely-mocked press conference at a Philadelphia landscaping center. It began when President Donald Trump announced on Twitter that Giuliani would hold a press conference at the Four Seasons. Trump deleted that original tweet and offered another, explaining he wasn’t talking about the posh downtown hotel, but Four Seasons Total Landscaping, conveniently located between Fantasy Island Adult Bookstore and the Delaware Valley Cremation Center on the outskirts of town.

As if the venue wasn’t embarrassing enough, in the midst of the live televised presser, Giuliani was informed the news departments of America’s major TV networks had just called the election for Joe Biden. On cue, Giuliani provided a bonkers meltdown that could be used verbatim as the script for an SNL sketch. “Oh my goodness! All the networks. Wow!” Giuliani said sarcastically, adding, “Networks don’t get to decide elections. Courts do!”

A reporter for Canada’s CBC News who attended the event offered her take on what she’d witnessed, describing the scene as “chaotic, confusing and a bit surreal.”

Dripping hair dye during unhinged press conference

For most people, the Four Seasons Total Landscaping disaster would mark an all-time low. When it came to Rudy Giuliani’s increasingly frantic attempts to overthrow the presidential election, he hadn’t even come close to hitting bottom.

Case in point: his subsequent press conference with Trump’s legal “dream team” (one of whom would be fired shortly after), once again offering no evidence to substantiate claims of voter fraud. Rather than citing laws and statutes, Giuliani instead referenced the 1992 comedy My Cousin Vinny while sweating profusely.

Thanks to that excessive perspiration, the presser became downright bizarre when, as the sweaty lawyer ranted, dark liquid began oozing down both sides of Giuliani’s face. As the goo dripped down, the live-streamed broadcast of the press conference — featured on the Trump campaign’s YouTube and Facebook platforms — included a brief audio conversation from a pair of unidentified voices who didn’t realize their mics were live. “Can they hear us on the stream? I guess not,” says one (via The Independent), with the other replying, “You see f**king Rudy’s hair dye dripping down his face?” The Trump campaign later claimed (without proof) the live feed had been improperly accessed by “unauthorized users.” 

Rudy Giuliani's own daughter came out against him

What does it say that Rudy Giuliani’s own daughter apparently disagrees with him so much she wrote a lengthy op-ed for Vanity Fair, declaring she would be voting for Joe Biden in the upcoming presidential election?

“If being the daughter of a polarizing mayor who became the president’s personal bulldog has taught me anything, it is that corruption starts with ‘yes-men’ and women, the cronies who create an echo chamber of lies and subservience to maintain their proximity to power,” wrote Catherine GIuliani. “We’ve seen this ad nauseam with Trump and his cadre of high-level sycophants (the ones who weren’t convicted, anyway).”

In a subsequent post-election piece for Vanity Fair, Giuliani’s daughter offered some hilariously scathing “self-care tips” for “Trumpworld” to help them come to grips with the fact that Trump lost the election. “Take stock of your failures,” she wrote. “Only sociopathic narcissists have delusions of grandeur, blaming others for their failings, often with tragic consequences.” She also took a shot at her father’s hair-dye fiasco by writing, “Avoid charcoal products or anything with artificial dyes, which may result in your face oozing as you make false claims of voter fraud in Philadelphia, for example.”

His embarrassing performance in court

According to NBC News, the last time Rudy Giuliani argued a case in federal court was 1992. Yet to describe his performance in a Philadelphia courtroom in November 2020 as “rusty” would be an insult to rust. 

As The Patriot News reported, rather than present evidence, Giuliani instead “threw around wild, unsupported accusations about a nationwide conspiracy by Democrats to steal the election.” Highlights of Giuliani’s return to the courtroom included mistaking the judge for a different judge, describing an opposing attorney as “the man who was very angry with me, I forgot his name,” and not knowing what “opacity” means; as Law & Crime pointed outGiuliani guessed it “probably means you can see,” while the judge corrected him by instructing that “it means you can’t.”

While he may have previously referenced My Cousin Vinny, Giuliani’s response to a standard legal query played out like a scene from the movie. In legalese, there are three levels of review that can be used to determine a statute’s constitutionality — the rational basis test, the intermediate scrutiny test, and the strict scrutiny test. When asked by the judge which standard he wanted applied, Giuliani responded, “The normal one.”

Reports that Rudy Giulani asked for a preemptive presidential pardon

There’s no denying that the activities Rudy Giuliani has undertaken on behalf of President Donald Trump have brought him scorn and humiliation, but could they potentially send him to the slammer? 

According to a report in The New York Times, Giuliani is alleged to have thought so. As a result, claimed two sources, he discussed the “possibility of receiving a pre-emptive pardon” before the president ended his single term in office. While the Times indicated the extent of Giulani’s criminal exposure was “unclear,” the newspaper also reminded that he was the subject of a federal investigation due to some allegedly shady business dealings in Ukraine, along with his alleged role in the removal of the American ambassador to Ukraine, all part of the assorted shenanigans that led to Trump’s impeachment. 

Contacted by the Times for confirmation, a spokesperson said, “Mayor Giuliani cannot comment on any discussions that he has with his client.” However, just 25 minutes before that, Giuliani himself headed to Twitter to say, “#FakeNews NYT lies again. Never had the discussion they falsely attribute to an anonymous source. Hard to keep up with all their lies.” 

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