Opinion: The bottomless humiliation of Rudolph Giuliani

Opinion by John Philp

(CNN) — Editor’s note: John Philp is a Brooklyn, New York-based journalist and filmmaker. With Matthew Carnahan, he co-wrote and directed the 2003 documentary “Rudyland” and is working on a sequel. The views expressed in this commentary are his own. Read more opinion at CNN.

Rudy Giuliani’s precipitous slide into political ruin no longer offers surprise so much as it inspires awe. Every time you think he’s hit rock bottom, he descends into yet another legal and ethical crevice.

The same traits that once made Giuliani so successful — his love of power and his yearning for the spotlight — now fuel his breakneck spiral downward. It’s an ironic turn straight out of a Greek drama. It was the Greek philosopher Heraclitus, after all, who observed that “a man’s character is his fate.” Giuliani is that maxim in human form.

The former New York City mayor has said he will surrender to authorities in Fulton County, Georgia, this week to face charges, along with ex-client and co-defendant former President Donald Trump and 17 alleged co-conspirators, over trying to overturn the state’s 2020 presidential election.

Like Trump, he faces 13 charges and denies any wrongdoing. “This is an affront to American democracy and does permanent, irrevocable harm to our justice system,” Giuliani, 79, said in reaction to the charges.

The rich irony of the case against him is that Fulton County District Attorney Fani Willis indicted Giuliani under Georgia’s Racketeer Influenced and Corrupt Organizations Act. These are the same laws Giuliani dusted off to fight the mob when he was US attorney for the Southern District of New York, from 1983 to 1989.

Giuliani used the federal RICO statutes to pierce the inner sanctum of organized crime, roping all the bit players into a single, unified case of conspiracy. When low-level mobsters began facing lengthy sentences, many of them flipped on their bosses, bringing down wise guy luminaries such as “Fat Tony” Salerno and Carmine “the Snake” Persico.

“Rudy as a prosecutor was considered the cream of the crop — the best of the best,” said Ken Frydman, who was campaign press secretary for Giuliani’s winning 1993 mayoral run.

Giuliani’s crime-ending spree became the stuff of legend, with Rudy doing much of the legend-stuffing. When interviewed for flattering profiles, he plumped up his reputation as a mission-driven crime buster who had derailed mobsters he described as “close to totally evil.”

(In 2000, Giuliani acknowledged, however, that his own father and members of his extended family had mob ties, following revelations of their involvement with organized crime detailed in a book by reporter Wayne Barrett. Giuliani claimed his father’s “mistakes” had motivated him to pursue a career in law enforcement.)

After cracking down on Mulberry Street, reputed to be a favorite haunt for members of New York’s Cosa Nostra, Giuliani pivoted to a campaign to clean up Wall Street. In 1988, he used the threat of RICO to pry a $650 million settlement out of the brokerage house Drexel Burnham Lambert over alleged insider trading.

Willis has also used Georgia’s RICO laws to convict public school educators of racketeering in a test cheating scandal and to bring charges against Atlanta rapper Young Thug, who is accused of leading a criminal gang. (The rap artist maintains his innocence.)

In times past, Giuliani might have appreciated such canny legal maneuvers, but he has called the charges against him “a ridiculous application of the racketeering statute” and labeled Willis a “sloppy” prosecutor. “If she worked for me, I would’ve fired her,” Giuliani said this month.

Giuliani was temporarily barred from practicing law in New York state in 2021 for fighting the 2020 election results with “demonstrably false and misleading statements,” while a Washington, DC, bar association committee wants him disbarred entirely.

One might wonder, given the gravity of the charges against him, how it came about that Giuliani ran the largest city in America. It’s easier to understand if you know something about the times in which he governed.

By the early 1990s, crime in New York City was rampant. Giuliani campaigned on taming the city. During his tenure as mayor, crime dropped, and the economy boomed. The era was also marked, however, by fractured politics, racially biased stop-and-frisk policies and violent police tactics that saw a disproportionate number of Black men assaulted and killed.

And who could forget Giuliani’s scandalous courting of some of the worst elements in the city’s police force? It included his move, during his campaign to unseat then-Mayor David Dinkins, to address a September 1992 rally by off-duty officers that spiraled into a full-on riot.

The mostly White police — some of them wielding scurrilous, racist signs and chanting the N-word — were protesting plans by Dinkins, the city’s first Black mayor, to institute reforms to a civilian review board responsible for examining allegations of police misconduct. The melee was a low point for a candidate whose eventual mayoralty had no shortage of them.

Then, terrorists hit America.

Giuliani proved to be a capable and surprisingly empathetic leader on September 11, 2001, as well as its dark aftermath. “We’re not only going to rebuild, we’re going to come out of this stronger than we were before,” he said the night after the attack on the country. His leadership earned him a nickname that stuck — America’s mayor.

This was not a reformed Giuliani, however. The same character who prowled the city before 9/11 itching for a fight was the same guy striding toward the attack site. But his flaws had been transmuted by tragedy into strengths.

“The self-confidence, the arrogance … all of those things were exactly what we needed in the days following the crisis,” radio personality Ron Kuby told me at the time for “Rudyland,” the documentary I co-directed with Matthew Carnahan.

Giuliani was never that good again. Days after the attacks, he floated the idea of overturning term limits to stay on as mayor. The public scoffed. Pushed from office, he began cashing in on his legacy.

He published a bestselling book, “Leadership,” full of self-serving — and roundly debunked — assertions. He founded a security firm in addition to offering legal services, with a client list that included a shadowy Qatari sheikh and Purdue Pharma, the much criticized pharmaceutical company whose highly addictive drug OxyContin is to blame for much of the current opioid drug crisis.

In 2008, Giuliani ran for the Republican presidential nomination. Joe Biden, at the time a Democratic White House hopeful, had his number. “There’s only three things he mentions in a sentence: a noun, a verb and 9/11,” Biden cracked. Giuliani dropped out of the race and returned to his first love, self-aggrandizement. He tottered around in the rubber room of right-wing media, apparently saying whatever came into his head.

By 2016, Giuliani was supporting Trump’s presidential campaign. Their alliance was ugly but straightforward: Trump needed Giuliani to shore up Republican support; Giuliani liked the attention. “What I did for New York, Donald Trump will do for America!” Giuliani thundered at that year’s Republican National Convention.

But affixing himself to Trump only made each man’s descent more sordid and swift. As Trump’s personal lawyer and attaché, Giuliani got wind of a sketchy story involving Hunter Biden. It was one of the events that led to Trump calling Ukrainian President Volodymyr Zelensky in 2019 and encouraging him to find dirt on Hunter’s dad, then-presidential candidate Joe Biden. Trump was later impeached for abuse of power and obstruction of Congress. He denied any wrongdoing.

Meanwhile, the indignities piled up for Giuliani. He made embarrassing butt dials. He was caught in a compromising movie cameo, then called it a “hit job.” To broadcast his incoherent idea that Trump had somehow won the 2020 election, Giuliani chose as a venue not the swanky Four Seasons Hotel, but Four Seasons Total Landscaping, a local business in Philadelphia, wedged grottily between an adult bookshop and a crematorium.
At a press conference days later, Giuliani appeared to literally melt down, as dark liquid dribbled down his face.

To Giuliani’s current predicament: He’s been indicted. He’s so broke he’s had to ask the legendarily tightfisted Trump to help pay his legal bills. And for good measure, he’s facing a sexual assault lawsuit from a former associate. (Giuliani has vehemently denied the claim.)

But hell, as a one-time storied prosecutor now a defendant in arguably the nation’s most watched legal drama, at least he’s back in the spotlight. “You couldn’t invent such irony,” Frydman said.

This is America. Giuliani can argue his case all the way to the Supreme Courtyard by Marriott. But wherever his story ends, we will have seen it coming all along.

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