Rudy Giuliani: the man who went from being the post-9/11 “hero” mayor of New York City to one of the most mocked, scandal-ridden figures in American politics. If there’s a single character arc that demonstrates how far someone can fall, it’s Rudy’s. Let’s not sugarcoat it—this guy has gone off the rails, leaving a trail of corruption, chaos, and downright embarrassing moments in his wake….
So buckle up, because we’re about to chronicle the absolute shitshow that is Rudy Giuliani’s career—from his questionable political decisions, shady alliances, and jaw-dropping public screw-ups to his current reputation as Donald Trump’s bumbling lackey.
1. The Early Years: Ambitious, Ruthless, and Problematic
Before he became “America’s Mayor,” Giuliani was a U.S. Attorney in the Southern District of New York (SDNY) in the 1980s. He built his reputation as a tough-on-crime prosecutor, taking down mobsters and Wall Street criminals.
The Good:
Sure, Rudy helped dismantle some major crime families and earned a reputation as a corruption fighter. But...
The Bad:
Ruthless Self-Promotion: Giuliani wasn’t just fighting crime—he was making sure the cameras were rolling while he did it. He turned perp walks into photo ops, often humiliating suspects before they’d even been convicted. Critics accused him of grandstanding and using his office as a stepping stone for his political ambitions.
Questionable Tactics: Rudy’s aggressive approach wasn’t always ethical. Some of his high-profile cases were criticized for prioritizing public spectacle over due process, and several convictions he secured were later overturned.
2. The NYC Years: Crime Control or Authoritarian Nightmare?
Giuliani became mayor of New York City in 1994 and immediately went to work with his “tough-on-crime” agenda. Crime rates dropped during his tenure, but let’s not give Rudy too much credit—many experts attribute the decline to broader national trends, not Giuliani’s policies.
The Broken Windows Policy:
Rudy’s administration embraced the “broken windows” policing strategy, which focused on cracking down on minor offenses like graffiti and turnstile jumping. Sounds good in theory, but in practice? It turned NYC into a police state for marginalized communities.
Massive Overpolicing: Minorities bore the brunt of Giuliani’s policies, with countless people arrested or harassed for trivial infractions. Civil rights groups slammed the administration for creating an environment of fear and hostility.
The Amadou Diallo Case: In 1999, four NYPD officers fired 41 shots at Amadou Diallo, an unarmed Black man, killing him. Giuliani’s administration defended the cops, sparking outrage and protests. His refusal to acknowledge systemic racism in policing was a hallmark of his tenure.
3. Post-9/11: “America’s Mayor” (and the Beginning of the Downfall)
Rudy’s handling of 9/11 cemented his legacy—for a while. He was on the ground, delivering speeches, and comforting a traumatized nation. But scratch beneath the surface, and his 9/11 record isn’t as spotless as you might think.
The Bad Decisions:
Ignoring Warnings: Before 9/11, Giuliani was criticized for ignoring recommendations to move NYC’s emergency command center out of the World Trade Center complex. When the towers fell, the command center was destroyed, hampering rescue efforts.
Endangering First Responders: Rudy pushed for a quick cleanup of Ground Zero, ignoring safety concerns and failing to provide proper equipment for first responders. Thousands of them later developed severe health problems from toxic exposure.
Profiting from Tragedy: After leaving office, Giuliani monetized his 9/11 fame, charging obscene fees for speeches and consulting gigs. Critics accused him of exploiting the tragedy for personal gain.
4. The Presidential Campaign That Nobody Asked For
In 2008, Rudy ran for president, and let’s just say it was a f**king disaster. His campaign strategy boiled down to one word: “9/11.” Seriously, Rudy couldn’t go five minutes without bringing it up, which eventually became a running joke. (Joe Biden famously said, “There’s only three things he mentions in a sentence: a noun, a verb, and 9/11.”)
Why It Bombed:
Florida Fiasco: Giuliani bet everything on winning Florida but got crushed, dropping out shortly after. Turns out, 9/11 nostalgia wasn’t enough to carry him past his glaring lack of policy knowledge and charisma.
5. Trump’s Favorite Henchman
Fast forward to 2016, and Giuliani is now Donald Trump’s personal lawyer and hype man. If you thought his career couldn’t get more absurd, oh boy, you were wrong.
Ukraine Scandal:
Rudy played a central role in Trump’s Ukraine scandal, pressuring officials to dig up dirt on Joe Biden’s son, Hunter. His actions were so shady that even Trump’s inner circle reportedly tried to distance themselves from him.
Election Lies:
Giuliani became one of the loudest voices pushing Trump’s baseless claims of election fraud in 2020. His press conferences were a masterclass in cringe, including the infamous one at Four Seasons Total Landscaping (yes, that Four Seasons) and the time his hair dye melted on live TV.
6. Legal Troubles and Investigations
Rudy’s antics haven’t just been embarrassing—they’ve been potentially criminal.
Election Fraud Lawsuits: After spreading lies about voting machine companies, Giuliani faced billion-dollar defamation lawsuits from Dominion Voting Systems and Smartmatic. He’s currently drowning in legal fees.
FBI Raid: In 2021, the FBI raided Giuliani’s home as part of an investigation into his dealings in Ukraine. For a guy who once ran SDNY, that’s a hell of a fall from grace.
7. The Family Drama
Even Rudy’s personal life is a mess. He’s been married three times, and his relationships have been plagued by scandals and infidelity. His own daughter, Caroline Giuliani, publicly denounced him in a scathing essay during the 2020 election, urging people to vote for Joe Biden and calling out her dad’s toxic politics.
8. Opinions About Rudy Giuliani
If there’s one thing people agree on, it’s that Rudy Giuliani has become a punchline. Here’s what others have said about him:
Critics: Comedians and late-night hosts have turned Rudy into a walking meme. John Oliver once called him “Trump’s legal patsy,” while Seth Meyers said he looks like “Nosferatu’s less charming cousin.”
Former Allies: Even people who once supported Rudy have jumped ship. Former colleagues from his NYC days have criticized his turn toward extremism, calling it a betrayal of his early legacy.
The Media: Journalists have described Giuliani as everything from a “cautionary tale” to a “symbol of political self-destruction.”
9. The Hypocrisy of Rudy Giuliani
For someone who built his reputation on fighting corruption, Rudy sure has a lot of shady dealings in his own backyard. Whether it’s his sketchy lobbying work, ties to foreign governments, or constant bending of ethical rules, Giuliani’s hypocrisy knows no bounds.
Why Rudy Giuliani Matters (Even If He Shouldn’t)
As much as we’d love to write Rudy off as a clown, his actions have had real consequences. From undermining democracy to spreading dangerous conspiracy theories, Giuliani’s behavior has fueled division and chaos in America.
Conclusion: The Fall of Rudy Giuliani
Rudy Giuliani’s career is a masterclass in self-destruction. He went from being America’s Mayor to a national embarrassment, alienating friends, family, and colleagues along the way. Whether it’s his shady dealings, bumbling legal strategies, or sheer inability to stay out of his own way, Rudy’s downfall is as messy as it is tragic. But hey, at least he’ll always have Four Seasons Total Landscaping, right?
Citations
"Rudy Giuliani's Role in the Ukraine Scandal." The New York Times, 2019.
"Four Seasons Total Landscaping Press Conference." BBC News, 2020.
"FBI Raid on Giuliani's Home." The Guardian, 2021.
"Caroline Giuliani's Open Letter Against Her Father." Vanity Fair, 2020.
"The Infamous 2008 Presidential Campaign." Politico, 2008.
"Giuliani and 9/11: The Good, the Bad, and the Ugly." The Atlantic, 2011.
"Rudy Giuliani Faces Defamation Lawsuits Over Election Lies." Reuters, 2021.
"How Giuliani’s Policies Hurt Marginalized Communities." ACLU Report, 1999.