WASHINGTON, DC – NOVEMBER 19: Rudy Giuliani speaks to the press about various lawsuits related to the 2020 election, inside the Republican National Committee headquarters on November 19, 2020 in Washington, DC. (Photo by Drew Angerer/Getty Images)

Earlier this week there was a buzz of activity at Studio 8H, 30 Rockefeller Plaza, the home of Saturday Night Live. The iconic address is a New York institution, but it was another New York institution that the SNL writers had in their sights: Rudy Giuliani.

Over the past few years, the former Mayor has gone from toast of the town to roast of the town, lampooned by late-night hosts and skewered by the city he helped bring back from the brink following 9/11.

Once a political pinup he is now a political punchline, parroting President Trump’s unproven claims about election fraud while inserting himself into increasingly hilarious press conference mishaps.

If Rudy Giuliani’s image was on life support after the Four Seasons Total Landscaping carpark caper, it flatlined following the hair dye fiasco.

Today it was confirmed by President Trump (via a tweet, naturally), that Rudy Giuliani had tested positive for the coronavirus. It is the latest headline in a career that has become defined by headlines.

But for those who are old enough to remember, or young enough to care, Rudy Giuliani used to be more than Trump’s attack dog. A wily politician and ruthless prosecutor, we take a look back at the rise, fall, and plummet of one of America’s most tragic figures.

Rudy vs The Mob (1985)

In the early 1980s, Rudy Giuliani was already making a name for himself in the US Attorney’s office. But it wasn’t until 1985, two years after he was appointed United States Attorney for the Southern District of New York, that Rudy became a household name thanks to the Mafia Commission Trial.

New York, N.Y.: FBI director William Webster (left) and Rudolph Giuliani, U.S. Attorney for the Southern District of New York (right), with a crime family chart during a press conference on mob arrests on February 26, 1985 at Federal Plaza in Manhattan. (Photo by Alan Raiai/Newsday RM via Getty Images)

With Giuliani at the helm, the US States Attorney office brought a wide-ranging set of charges against New York’s Five Families. Using the RICO Act (Racketeer Influenced and Corrupt Organizations Act), Giuliani was able to arrest and prosecute the heads of all Five Families, a near-fatal blow to organised crime in New York.

9/11 and The Mayor of America (1994-2001)

Goodwill flowed Giuliani’s way following the Mafia Commission Trial, so he sets his sights on public office. A 1989 bid for New York City Mayor ended in defeat, but four years later Giuliani would emerge victorious.

As a second-generation Italian immigrant, no one was more Nu Yawk then Giuliani, and he was able to leverage his tough on crime legal career into a pillar of his mayoral style. His war against petty crime proved popular, and as crime rates in New York city dropped, Giuliani’s popularity soared.

But it was our generations most televised tragedy that proved to be the making of Rudolph Giuliani. When the Twin Towers fell on 11th September 2001, New York had its heart ripped out as the world watched on in horror.

NEW YORK, NY – NOVEMBER 14: New York Mayor Rudolph Giuliani (center right with red tie) and Secretary of Defense Donald H. Rumsfeld (center left in fire department jacket) tour “Ground Zero” of the World Trade Center ruins 14 November 2001 in New York. (Photo credit should read ANGEL FRANCO/AFP via Getty Images)

What they saw in the days, weeks and even months after, was Mayor Giuliani standing amongst the rubble reminding his people that nothing can defeat New York.

“The number of casualties,” he said, “will be more than any of us can bear, ultimately.”

His deft handling of a national crisis in front of a global audience thrust Giuliani into the spotlight. People around the world knew his name, people around the country pointed to his strength. Shortly after the attacks, at a prayer service at Yankee Stadium, Oprah Winfrey introduced Giuliani as “America’s Mayor.”

A sign of things to come.

Time Person of the Year (2001)

Off the back of his leadership during 9/11, Giuliani was named Time’s 2001 Person of the Year “for having more faith in us than we had in ourselves.”

Rudy Giuliani appears on the cover of TIME Magazine after being named Person of the Year.

“When the day of infamy came, Giuliani seized it as if he had been waiting for it all his life,” read the Time profile. “Taking on half a dozen critical roles and performing each masterfully.”

Rudy for President (2007)

According to a 2006 pre-election poll, Giuliani was the most popular politician in America, so it was hardly surprising when he decided to run for President.

Republican presidential hopeful Rudy Giuliani poses for a group photo with some high school students following his campaign stop at Valley High School, Tuesday, April 3, 2007, in West Des Moines, Iowa. (Photo by Mark Hirsch/WireImage)

Registering as a Republican, Giuliani established a healthy lead in 2007, with many pundits tipping the former prosecutor to be the party’s nominee ahead of war hero John McCain. But then skeletons in Giuliani closet began to emerge, thwarting his chances. Reports that while in office the former NYC mayor used his expense account to visit his mistress in the Hamptons proved damaging and in January 2008 he formally withdrew, throwing his support behind McCain.

Team Trump (2016 – Present)

Having spent the Obama years making bank on the public speaking circuit, Giuliani reemerged in 2016 to become a vocal supporter of Donald Trump. His passionate outbursts and hardline politics caught many by surprise: “Is Rudy Giuliani OK?” asked The Washington Post in August 2016. One month later, Politico upped the ante even further: “Is Rudy Giuliani Losing His Mind?

Based on his behaviour over the past four years, the answer to both of those questions is, who knows?

Since becoming a permanent fixture in the Trump camp, Giuliani has never been far from controversy, helping the President wade through a sea of scandals. He was by Trump’s side for the impeachment trial while also being a key player in the Ukraine debacle.

WASHINGTON, DC – SEPTEMBER 27: Former New York Mayor Rudy Giuliani listens as U.S. President Donald Trump speaks during a news conference in the Briefing Room of the White House on September 27, 2020 in Washington, DC. Trump is preparing for the first presidential debate with former Vice President and Democratic Nominee Joe Biden on September 29th in Cleveland, Ohio. (Photo by Joshua Roberts/Getty Images)

The Gaffe Magnet

There’s an obvious parallel in Trump’s refusal to concede the election, and Giuliani’s refusal to concede his time in the sun is done. Both men cling to relevance even as embarrassment piles up around them, their supporters becoming more sparse, less likely to lend a hand.

Giuliani has endured a particularly horrid time of late, with a series of public gaffes adding new gravity to the question posed by The Washington Post four years ago. Is Rudy Giuliani, OK?

First came his unflattering cameo in the new Borat film, which captured the 76-year-old in a compromising scene with the actor playing Borat’s daughter.

Then came the Four Seasons Total Landscaping disaster, the press conference heard around the world. Here was Rudy Giuliani conjuring up conspiracy theories about voter fraud while standing in a strikingly unglamorous car park.

PHILADELPHIA, PENNSYLVANIA – NOVEMBER 07: Attorney for the President, Rudy Giuliani speaks to the media at a press conference held in the back parking lot of landscaping company on November 7, 2020 in Philadelphia, Pennsylvania. The press conference took place just minutes after news networks announced that Joe Biden had won the presidency over Donald Trump after it was projected that he had won the state of Pennsylvania. (Photo by Chris McGrath/Getty Images)

And perhaps the final straw, a literal melting down caught on camera. Having assembled the media for yet another meandering election update, Giuliani’s message was overshadowed by brown streaks that poured ominously from the sides of his head. While it’s unclear if the streaks were a result of cheap hair dye or a last-minute touch up from a (presumably now fired) makeup artist, the internet had a field day.

The great Rudolph W. Giuliani, the bastion of New York City, the Mayor of America. Reduced to nothing more than a sweating meme.

Tile image credit: Andrew Lichtenstein / Corbis via Getty Images

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