Rudy Giuliani: Unmasking The Mayhem Behind The Mayor

Rudy Giuliani is one of my favourite politicians.

No not because I agree with his politics, because he kind of reminds me of that Mayor from Spin City, who did ridiculous things, and you’d roll your eyes and be like, “no one is that ridiculous, this is just poorly written, far fetched comedy.” But, if the writers for Spin City hit a bunch of acid, and then had a brainstorming session on a camping trip in Times Square, perhaps they might be able to envision Rudy Giuliani. 

I mean think of Danny DeVito as the Penguin in Batman, but much more of a sexual predator, and much more shameless. For example, Rudy was just in the news for allegedly trying to sell Presidential Pardons for a couple million bucks. And it got me thinking, we should look into his past and tell a story about how amazingly insane of a political figure he is.

In today’s video, we are going to dive into the intriguing life and times of Rudy Giuliani, a man known for his audacious character who has taken on roles from New York City’s mayor to President Trump’s  personal attorney. And of course, we’ll touch on the good stuff, like the Four Seasons Press Conference and his run in with Borat.

Let’s dive right in.

A brief background on Rudy Giuliani

Let’s start with how Rudy Giuliani got here.

The scene? 1968. A young Rudy, fresh out of law school and brimming with idealism. Shockingly enough, he was a card-carrying Democrat, volunteering on Robert F. Kennedy’s 1968 presidential campaign. 

Giuliani’s first notable sign of character came when he was able to skirt military service in Vietnam thanks to a few well-timed deferrals. He did this by becoming Judge MacMahon’s law clerk and earned himself a ‘get out of the draft free’ card, being recategorized as an “essential civilian.” When his number did eventually come up in the lottery, it was high enough to keep him safely on the sidelines. Ah, the wonders of chance!

By 1980, he made the full switch to being a Republican after Reagan’s win. He cited a disillusionment with Democratic policies, but critics suspected a strategy to ascend within the Justice Department. One of those critics being his own mother, who suggested his Republican shift was opportunistic.

Newsday headline, November 4, 1993

Under Reagan, Giuliani spent most of the 80s serving as Associate Attorney General for the Southern District of New York where he aimed to personally litigate cases. His prosecution of Wall Street moguls like Boesky and Milken positioned him as a strong anti-corruption figure. 

Known for his public “perp walks,” ironically Giuliani left his U.S. Attorney post in ’89 amidst controversy over his perceived political leveraging of prosecutions.

After several failed attempts, Giuliani became NYC Mayor in ’94, holding office until ’01. His term was known for shooing away sex clubs, drug dealers, and panhandlers from the Big Apple, known as the ‘civic cleanup.’

9/11 and the role of mayor

But there was something else that really helped Rudy build his brand.

Giuliana got thrown into the Spotlight in 2001 after the 9/11 attacks. Let me set the stage for how much support existed for New York and how sensitive America became at the time of the terrorist attacks.

For example, at the time of the attacks Bill Maher had Jimmy Kimmel’s spot on ABC for a show called Politically Incorrect. He made a comment about how Americans were constantly referring to the terrorists as ‘cowards’ at the time, and how he didn’t agree with that use of language. The discussion of the use of the word ‘coward’ cost him his show.

The point that I am trying to drive here, is that when tragedy happens, the decent thing to do is be supportive and sensitive. New York saw this in spades. And with 9/11, Giuliani had an opportunistic moment and he took full advantage.

Consider this, after being thrust into the national spotlight Rudy earned the title of Time’s ‘Person of the Year‘ in 2001. Again, we could have had a seagull as mayor of New York that year and they would have been just as likely to be Time’s Person of the Year.

Source: Time

Just listen to this. In the aftermath of 9/11, Giuliani asserted that he was down in the trenches just as much as any other worker, soaking up the same potentially harmful elements as the hardworking folks dedicated to recovery and restoration. 

Sounds like a moving soliloquy, until the facts had the audacity to tell a different story. It seems the then Mayor logged in a whopping 29 hours at Ground Zero over three months starting September 17th. If you’re wondering, recovery workers chalked up this much time in a span of 2 to 3 days in the aftermath.

It doesn’t end there. 20 years later he gave a speech at a 9/11 memorial dinner and showed up totally bombed.

The Trump connection

Once his mayorship was up, Rudy began his descent into what can only be described as an endless tirade of bizarre scandals. 

Let’s move forward to 2008. 

Giuliani is vying for the Republican nomination. And who do you think is there waving a flag for his campaign? None other than Donald Trump. And it’s crazy to think, but this little troll doll actually led the polls for the Republican primaries for almost a year.

Despite Trump’s financial support, Rudy’s campaign eventually sputtered and stalled out, but don’t worry, this is just the start of their intriguing tango.

A few election cycles later, and Trump is now the one running for president. At this point, Giuliani, is comfortably settled into civilian life and sees his chance and returns the favor. Not only does he endorse Trump, but he hits the campaign trail for him, shouting his praises to the rafters. 

After Trump’s stunning victory, the freshly elected President crowned Giuliani the coveted mantle of “informal cybersecurity adviser,” and then created the Cybersecurity and Infrastructure Security Agency in November 2018. 

Giuliani’s credentials in cybersecurity? Well, let’s just say that forgetting your iPhone’s passcode and running off to the Genius Bar doesn’t exactly scream “cyber guru.”

The Mueller investigation

Now here’s where things really start to heat up.  

In April 2018, special prosecutor Robert Mueller was on the prowl, investigating Russian interference in the 2016 elections, and Trump’s in the hot seat. Enter Giuliani, riding in like a white knight to join Trump’s personal legal team and play cleanup on aisle Russia— and fast.

Giuliani took a stand for the president’s right not to testify in the special counsel investigation, citing a ‘magically shifting memory’ as the reason. One of Giuliani’s most memorable nuggets of wisdom came on August 19th during an episode of Meet the Press when he argued that the president could be led into a perjury trap, simply by reciting someone else’s version of the truth, coining the philosophical gem, “Truth isn’t truth.”

The Four Seasons presser

But here is my personal favourite Giuliani story. With the eyes of the world trained on the US election results, tensions high, and Rudy Giuliani looking to defend his boy Trump. He elects to call a press conference at the Four Seasons. Sounds classy, right? 

Trump even tweeted about.

Just one tiny problem. This wasn’t the swanky Four Seasons Hotel. Rather, Giuliani fumbled the booking. This was Four Seasons Total Landscaping company, a humble business nestled between an adult bookstore and a crematorium. But the show must go on, despite how ridiculous it appeared to…. Well… everybody.

Giuliani steps up to the podium, knowing he’s sandwiched between ‘Fantasy Island Adult Books’ and ‘Delaware Valley Cremation Center’ instead of sipping a martini at a high-end hotel.

He goes on to propagate Trump’s claims of election fraud sans any evidence, justifying the refusal to concede the election. 

The Four Seasons Hotel was quick to wash its hands of this bizarre debacle, leaving Four Seasons Total Landscaping to deal with the fallout. But what did they do? They didn’t run and hide. Nope. They issued a statement, emphasizing their non-partisan, family-owned small business status, and then started selling merchandise related to the event. 

As for the Trump campaign, they kept mum about whether this was a mistake or an intentional choice, leaving the rest of us in stitches from all the jokes flying around on social media. 

The Four Seasons saga will live on as a testament to Giuliani’s uncanny ability to turn even the most mundane event into a spectacle of epic incompetent proportions. There’s just so much more. Of course, shortly after, Giuliani showed up at a press conference making similar election claims, with hair dye running down his face.

Pay for pardon

More recently, Giuliani has been accused of sexual assault and running a “pay for pardon” scheme during Trumps final two years in office. Noelle Dunphy, a former employee of Giuliani’s firm from 2019 to 2021, emerged from the shadows in May 2023 and threw a lawsuit grenade into the fray. 

If you read the lawsuit, it’s basically what you would expect. 

Take a look at Item 108: 

Source: Court filing

It’s like dating Louis CK. But not nearly as funny.

And then she told Inside Edition this:

So, Rudy demanded she give him a blow job while he talked to Trump on the phone and then pretend he was Donald Trump? I mean I assumed he was a freak, but I mean, that’s Randy and Lahey stuff right there. Except for the consensual part I guess.

But, Dunphy also alleges Giuliani was selling presidential pardons like hotcakes for a cool $2 million a pop, with the proceeds to be split evenly with Trump. However, as of now, there’s no evidence to back this up.  But you know what they say – where there’s smoke there’s fire.

The Borat Subsequent Moviefilm

The allegations, while remaining unproven, are hardly shocking to anyone that watched the sequel to cult comedy Borat, the Borat Subsequent Moviefilm, released in 2020. Giuliani’s role in the film might be considered the pièce de résistance of his screw ups. 

The scene plays out like a sitcom with a side of cringe: Giuliani is in a hotel suite with an actress playing Borat’s “daughter,” who’s posing as a 15 year old TV journalist. After the interview, our favorite gaffe-prone attorney is seen reclining on the bed, tucking in his shirt and “reaching into his trousers.”

Now enters Borat, exclaiming that his “daughter” is 15 and “too old” for Giuliani. 

After the uproar upon the films release, with a tweet that reads like a desperate plea, Rudy calls the film a “complete fabrication,” labels Sacha Baron Cohen a “stone-cold liar,” and denies any inappropriate behavior.

Wrapping it up

Okay, so we’ve taken a stroll down the scandal-ridden memory lane of Rudy Giuliani. And we literally ran out of time to keep going. Because my editing staff, god bless them, only have so many hours in a day. So let’s wrap it up.

In the age of social media, where every citizen is a potential fact-checker, Rudy’s style of opportunistic politics has hit a brick wall. The man who used to manipulate a handful of TV channels and newspapers for his own gain is now left scrambling in a digital landscape that refuses to let his falsehoods fly unchallenged. 

Social media has decentralized and democratized the media landscape in a way that we now can all laugh at for just how absurd of an individual Rudy has is. I mean, he has done the unthinkable. He makes Trump seem like the voice of reason; like a man of integrity. One has to wonder, in his quiet moments, does even Trump look at Rudy and think, “Man, I’ve got to distance myself from this guy.”

It’s baffling that not so long ago, this ‘Spin City’ meets ‘Batman’s Penguin’ figure was leading the Republican primaries. In a world where politicians spin webs of untruths as a matter of routine, there’s something hilariously unique about Giuliani’s brand of BS. Giuliani is like a circus sideshow you just can’t look away from – terrifying, bewildering, and so absurd you can’t help but laugh. 

I hate all politicians and think they are opportunists, no one leaves a high paying job for a low paying job, to be scrutinized by the public, unless of course they are getting paid in some way shape or form. The amount of side deals Rudy must have done as mayor of New York is baffling to even begin to ponder. But, don’t hate the player, hate the game.

Rudy is just such a mess, that I think he’s my favourite politician. Here’s to you, Rudy – the punchline that keeps on giving. And let’s just hope you never wind up with any real authority.

Information for this briefing was found via the New York Times, Time, Wall Street Journal, Washington Post and the sources mentioned. The author has no securities or affiliations related to this organization. Not a recommendation to buy or sell. Always do additional research and consult a professional before purchasing a security. The author holds no licenses.

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