Few of those​ who lived in New York City during the Mussolini reign of Mayor Rudolph Giuliani would have pictured him playing out his sallow years as a dwarfish punch line—a cheap laugh. It is near impossible to think of any once respected figure who has subjected himself to such dunks of dank humiliation.

Other politicians reaching for the ring of power have taken slapstick spills or made memorable gaffes (Rick Perry, with his celebrated ‘Oops’ during a Republican presidential candidate debate, Dan Quayle misspelling ‘potato’), providing comic relief before receding into the ranks of also-rans, but Rudy—as he is familiarly, and not affectionately, known—has exerted true staying power. Despite not having held elective office in two decades or making any useful contribution to the commonweal as a citizen, Giuliani has managed to remain a political burlesque act, clinging to the slim consolation that tawdry fame is better than no fame at all.

The contrast between Rudy Then and Rudy Now is so stark that it has produced its own genre of journalism. An ostensible straight arrow from the school of hard knocks, a commando foe of graft and corruption, the younger Giuliani dressed sharp, acted sharp and talked sharp, cutting a clean swath with a killer grin. Middle age brought out a rounder, preenier side, immortalized in 2000 in a video that showed him sashaying in matronly drag and preening for Donald Trump like a cross between Barbara Cartland and a funeral bouquet, a grotesque flirtation that proved prophetic.

Giuliani, at the time the mayor of New York, dressed as Marilyn Monroe, 1997.

These two were fated to be mated. As the courtier, roving fixer and tireless mouthpiece for the Burger King of Palm Beach, Giuliani would relinquish all shame, honor, dignity, self-respect and semblance of continence. According to Maggie Haberman’s Confidence Man: The Making of Donald Trump and the Breaking of America, he stank up the bathroom on one of Trump’s campaign planes so badly that Trump bellowed, ‘Rudy! That’s fucking disgusting!’ as Rudy hustled back to his seat.

Under hot lights his hair dye dribbled as if his head had sprung an oil-can leak. He was nearly caught in a compromising position with a young actress pretending to be underage in the convoluted Borat Subsequent Moviefilm mockumentary. Then there was the shlock folly of the Four Seasons press conference held not at the regal Four Seasons hotel in Philadelphia, as was presumably intended, but at the garage door of Four Seasons Total Landscaping, on the same block as a sex shop and a crematorium.

As the courtier, roving fixer and tireless mouthpiece for the Burger King of Palm Beach, Rudy Giuliani would relinquish all shame, honor, dignity, self-respect and semblance of continence.

None of these doofus mishaps has endeared him to his detractors. His toxicity levels are too high. When Giuliani was revealed as a mystery contestant on Fox’s The Masked Singer, one of the judges, Ken Jeong (Knocked Up, the Hangover movies), walked off the set in disgust.

A run-down windup doll, Giuliani seems oblivious to the slapping waves of mocking laughter or outright ire that he provokes, unchastened, undaunted, and is never at a loss for half-assed excuses or conspiracy-mongering. Today he is reportedly broke, without allies, suspended from practicing law in New York and Washington, on the verge of indictment for election tampering, looking ever more vagabond. How did such a snub-nosed bullet of a phenomenon become such a miasmic mess?

The Auto-Destruct Apparatus

It can’t all be pinned on prostration to Trump: supplication is the norm where he is concerned. Ted Cruz, the invertebrate senator from Texas, remained deferential to candidate Trump even after Trump had disparaged his wife’s looks and floated the notion that Cruz’s father was JFK’s assassin. The former New Jersey governor Chris Christie, who fancied himself a Tony Soprano boss with a Bruce Springsteen soul, endured fat jokes onstage from Trump, hardly a ballerina himself. The activation of Lindsey Graham’s salivary glands whenever he rises up on his hind legs in defense of Trump and the MAGA agenda is a source of negative wonder.

Giuliani, here in his role as attorney for then president Donald Trump, conducts a news conference with hair dye dripping down his face.

It is a commonplace in pop psychology that highly strung executives and other overpaid ego charioteers seek out the ministrations of a dominatrix to relieve pent-up tension. While tongue-polishing the boots of Mistress Diandra in the privacy of a dungeon isn’t everyone’s dish of ice cream, it doesn’t take a lot of imagination to grasp the ritual appeal. But Trump’s gruff bark, jangly attention deficit and brand of obedience training seem to have little to recommend them, which makes Giuliani’s distended loyalty all the more mystifying.

Many fellow Trumpies seem poised to adopt the despotic Florida governor, Ron DeSantis, as their new ding-dong daddy, but Giuliani is still out there schlepping like Willy Loman, for all the good it’s done him. Of all of the patsies in the Trump orbit, none has squandered as much moral and reputational capital as Giuliani and secured for himself such a skanky place in history. Ten years ago he might have been saved from himself, but it’s too late to call in an exorcist now.

How did such a snub-nosed bullet of a phenomenon become such a miasmic mess?

A diagnostic study of Giuliani’s auto-destruct apparatus is probably beyond the capabilities of psychiatric case study. Norman Mailer or Mary McCarthy might have had a better shot at evoking what makes Rudy tick, much as Mailer examined the biomechanics of the ‘New Nixon’ in Miami and the Siege of Chicago and McCarthy taxonomized the cast of Watergate in The Mask of State. Both writers possessed an intuitive analytical cunning bordering on the shamanistic – Joan Didion as well.

But there aren’t many Mailers or McCarthys or Didions haunting the marble lobbies these days, and in the absence of literary falconry and lightning perceptions the reportorial diligence and personal proximity of Andrew Kirtzman will have to do. A longtime New York journalist and television host, Kirtzman is the author of the thundering Rudy Giuliani: Emperor of the City (2000), to which his new book, Giuliani: The Rise and Fall of America’s Mayor, is the sequel.

Giuliani and Trump at the groundbreaking for the Trump International Hotel & Tower, in New York, 1995.

Kirtzman possesses the salient advantage of having covered Giuliani close up for decades, witnessing his evolution from an Eliot Ness crimebuster to the Sheriff of Rottingham tasked with taming the crime and decay of America’s greatest metropolis. He plays fair. Unlike many reporters and pundits who view Giuliani almost solely through the fish-eye lens of the present, Kirtzman doesn’t trivialize his genuine achievements, first as US attorney for the Southern District of New York and then as mayor, nor does he discount the cost of the racial antagonism Giuliani stoked and exploited.

A run-down windup doll, Giuliani seems oblivious to the slapping waves of mocking laughter or outright ire that he provokes.

For decades, New York City seemed to be undergoing a permanent nervous breakdown, a roiling turmoil that helped produce punk, disco, the SoHo art scene, the silver age of Warhol and so many other things we cherish, but was hell on the infrastructure and fear index. Kirtzman credits Giuliani, despite his demagogic blustering and grandstanding, for getting the dirty job done in his two terms as mayor, attacking major crime by first taming minor crime and flagrant signs of rot and squalor. Kirtzman:

Laws against fare beating, urinating in public and pot smoking were enforced under Giuliani’s Broken Windows initiative. The homeless were rousted from the streets and forced to move along. Summonses for minor crimes ballooned from 175,000 to 500,000. The number of arrestees cycling through the Rikers Island jail system swelled by over 15,000. Misdemeanor arrests more than doubled.

Despite the price of over-zealousness, the campaign paid off. Seven years later,

New York was a far different city on this day than it was when he assumed the mayoralty from David Dinkins … You could read it in the numbers and feel it in the streets.

Crime was down nearly 60 percent. The murder rate was even lower; 1,250 fewer New Yorkers were killed in 2000 than in 1993. Car thieves stole more than 111,000 vehicles the year before Giuliani took office. The count was down to less than a third of that. City streets were not just safer; they were cleaner. Seventy-five percent of streets were rated clean when he was elected; the figure was now over 85 percent.

The city’s tax burden was the lowest in thirty years. Eleven million more tourists per year were jamming the city’s hotels. The local economy had finally joined the national upswing, buoyed by the booming tech industry. New skyscrapers and apartment towers were springing up across the city.

The improvements sparked a seismic change in how Americans saw New York, and how New Yorkers felt about their city.

The Take-Charge Guy

Extreme decisiveness can be more attractive to voters than dither and drift despite causing rifts in public opinion. The partisan sniping and polarization of the Giuliani era was put on pause after 9/11 as he rose to fill the unaccustomed roles of pacifier and unifier. In the immediate shock and chaos of the destruction of the Twin Towers, he became the take-charge guy, forging dynamically through the dust and rubble of Ground Zero.

Giuliani, left, with former U.S. Parole Commission chairman Benjamin Baer and former New York senator Al D’Amato. Each had bought crack to show how easy it was to get at the time, 1986.

His shabby decision-making had contributed to the death toll that day – through the location of the city’s emergency command center at 7 World Trade Center, ‘a proven terrorist target’, and the catastrophic foul-up of the radio communications system – but he brazened it out at a moment when so many others in authority were slack-jawed and frozen at the switches. ‘His performance on September 11 was a tapestry of inspired leadership and fatal mistakes,’ Kirtzman writes. ‘The public saw only part of the picture that terrible day; the rest was shrouded in adulation for years. He became a living legend, America’s mayor … It was inconceivable that the legend could have an expiration date.’

Waiting for the next summons to greatness to arrive, Giuliani eased on down the yellow brick road of celebrity, opening a law firm bearing his name, making countless TV appearances and hitting the speakers’ circuit with a helping of hard-won wisdom about leadership and fortitude – the usual Churchill for Chumps spiel.

“He became a living legend, America’s mayor … It was inconceivable that the legend could have an expiration date.”

What a cash cow 9/11 proved to be. ‘His outside income was … eye-popping. He signed a $2.7 million advance on a book deal with Harvey and Bob Weinstein’s Miramax Books, and delivered over a hundred speeches in his first year, crisscrossing the country for $100,000 or more per appearance. For all his ambitions for his firm, he was barely at the office.’ (‘His speaking-fee haul in 2002,’ Kirtzman writes, ‘was estimated at $8 million.’)

With great wealth comes great irresponsibility, and Giuliani sought the company of other glad-handing duffers and machers, joining nearly a dozen country clubs when one or two might have sufficed for schmoozing and networking purposes, buying a lavish Manhattan co-op and a palatial retreat in the Hamptons, and swanking it up with expensive cigars like General Patton on the eve of battle.

What Giuliani couldn’t know was that his greatest battles were behind him, waged in the five boroughs of New York, with the crisis and trauma of 9/11 non-transferable to other issues and other political stages. Basking in hero’s honors, fluffed and flattered wherever he turned, plumped and slathered like a Christmas goose, he could be excused for fancying himself precedent-defying – destiny’s darling, a man for all seasons. It’s hard to keep a lid on your fake modesty once you’ve received an honorary knighthood from the Queen.

What​ this biography conveys is that Rudy’s breaking bad wasn’t a sudden turn to the dark side. The hairline cracks in his moral and behavioral makeup were there from the outset. Time and temptation have a way of widening character flaws.

The Making Of

A war baby born in 1944, raised Catholic back when that carried a permanent stamp, Giuliani needed ‘a good amount of moral jujitsu just to get through childhood. He was educated by teachers preaching godliness, while his family members were a motley crew that included police officers, loan sharks and thugs.’ (‘Three cousins killed within five years,’ according to the investigative reporter Wayne Barrett, who uncovered the criminal past of Giuliani’s family in 2000. ‘A mob uncle and cousin. A cop uncle protecting the mob uncle.’)

Giuliani took pride in being a cocky nonconformist, a Yankee fan in a sea of Brooklyn Dodger fans (the purest blasphemy then), a college kid who dressed like an Eisenhower-era square but was peachy keen on JFK. His JFK admiration extended to a blithe disregard for marital fidelity. He broke the marriage vows to his first wife, Regina Peruggi, with cavalier abandon. ‘He cheated on her pretty much the whole time they were married,’ a friend of Peruggi’s told Kirtzman. Subtle tip-offs: ‘Giuliani’s wife found another woman’s jewelery in the house. Women she didn’t recognize rang their doorbell, looking for him.’

Giuliani takes a puff at Trump Golf Links at Ferry Point, in the Bronx, 2015.

Having wrecked his first marriage, this unlikely swinger proceeded to ruin his second. Wife number two was a household name and face to most New Yorkers, a local TV news anchor called Donna Hanover who would later make occasional appearances as a judge on Law & Order. The dissolution of their marriage became a tabloid circus at which Rudy played ringmaster. Kirtzman sets the scene. The year, 2000. The occasion, an annual banquet roast.

New York’s Inner Circle Dinner is an annual rite for the city’s political class, a boozy black-tie charity event filling the Hilton Hotel’s grand ballroom with hundreds of politicians, reporters, lobbyists and assorted government hacks and bottom-feeders. It’s a celebratory affair, with fat-bellied reporters and government spokespeople warbling off-key in ribald skits skewering politicians.

The highlight is the rebuttal performance by the mayor, which can be memorable and sometimes wildly inappropriate, as when Mayor Ed Koch sang and danced in an afro wig in 1980, sparking a walkout by Harlem’s congressman Charles Rangel. Happy to push boundaries to their extreme, Rudy Giuliani in his fourth year in office appeared onstage in full drag with the cast of the musical Victor/Victoria, a jaw-dropping moment that fed his bottomless appetite for shocking people …

But few in the audience picked up on the full depth of Giuliani’s audacity this evening. Sitting quietly at his table in place of Donna Hanover, hiding in plain sight in a room packed with hundreds of reporters, was the woman with whom he was having an affair.

Judith Nathan was the mistress and Hanover’s successor. Giuliani would announce the dissolution of his marriage in a press conference before he had even informed his then wife it was over.

Basking in hero’s honors, fluffed and flattered wherever he turned, plumped and slathered like a Christmas goose, Giuliani could be excused for fancying himself precedent-defying – destiny’s darling, a man for all seasons.

Not only did Hanover’s humiliation earn her the sympathy of nearly every bystander (hiring the publicity-hound divorce lawyer Raoul Felder to rough her up created even more of a backlash), it cost Giuliani any chance he had with women voters. This soap opera, along with a diagnosis of prostate cancer, compelled him to withdraw from a 2000 New York Senate run against Hillary Clinton.

Eight years later he tried to make a go of it as a presidential candidate, a campaign that belly-flopped with an ignominious splash after he came in third in the Florida primary. Giuliani learned the hard way that even the most popular, high-profile New York politician doesn’t play well in the yonder reaches of mid-America.

He was more socially and culturally moderate than mainstream Republicanism and the sullen, angry white base that Mailer dubbed ‘the Wad’. A man so armored with a sense of destiny and invincibility lacks the tact and maneuverability it takes to shift with the times and improvise on the fly, and Giuliani operated like a mechanized unit, self-programmed to parrot ‘Noun, verb, 9/11,’ in Joe Biden’s priceless quip. That wasn’t what the Wad wanted. What the Wad wanted, was waiting for, was Donald Trump.

Giuliani and Trump were fated to be mated.

The mind-meld between Giuliani and Trump goes back to mayoral days, when the city was big enough for the both of them. It was probably kindled on the solemn occasion when Giuliani did something uncharacteristic: he fawned.

The mayor walked through the grand, solid-bronze doors of the venerable Marble Collegiate Church on Fifth Avenue for the funeral of Fred Trump, Donald’s father. He marched up the center aisle’s red carpet, past dozens of pews filled with hundreds of members of the city’s corporate and political elite, stepped up to the dais, and turned to the audience. Fred’s casket, covered in white roses, was a few feet away.

‘Fred Trump was a very big man, a giant,’ Giuliani told the crowd. ‘Fred Trump not only helped to build our city, but helped define it.’

Giuliani introduces Trump, then the Republican presidential nominee, at a campaign rally in Greenville, North Carolina, 2016.

Even some of the mourners might have gagged at this Founding Father business, but it would have left a favorable impression on Trump, for whom no obeisance was too ornate or over the top. Temperamentally, the two men were sympatico – combative, freewheeling and culturally moderate – while feeding off some of the same prejudices. Trump’s racist policies as an urban landlord and Giuliani’s racist pot-stirring as hizzoner were joined at the hip. Post mayoralty, Giuliani insistently blamed and upbraided Black citizens for being the engineers of their own besetting problems, claiming that police shootings were the result of Black on Black violence and decrying the Black Lives Matter movement, an antipathy Trump shared.

What brought their free-floating racism into sniper focus was their mutual detestation of Barack Obama, who had the effrontery to be smooth, eloquent, slim, knowledgable, slyly ironic, a model of fidelity and fatherhood without nature’s bestowal of pasty skin. Trump’s ‘birtherism’ – his phony Inspector Javert pursuit of Obama’s birth certificate – and Giuliani’s rancid accusations that Obama didn’t love his country propounded the same calumny: that the first Black president was an alien usurper, a traducer of American values.

Also binding Trump and Giuliani was that both prized loyalty above a solid résumé or even basic competence, cultivating a permanently besieged us-versus-everybody-else Mob boss mentality. Giuliani was known for doing a nifty Don Corleone impression, but Trump was the true Godfather in their relationship, with Giuliani a mouthier consigliere – a Tom Hagen who never knows when to recede into the woodwork. A Tom Hagen who infallibly makes everything worse.

Giuliani was known for doing a nifty Don Corleone impression, but Trump was the true Godfather in their relationship, with Giuliani a mouthier consigliere.

Kirtzman’s remaining chapters detail his antihero’s inept, mendacious behavior in Ukraine, trying to dig up dirt on Hunter Biden and being snookered by a Russian asset, and his even more baseless, unconscionable efforts to monkey-wrench the results of the 2020 election through stunts and feckless lawsuits, flapping papers around like Joe McCarthy brandishing his list of State Department Commies.

At this point Giuliani becomes less a political operative than a paranormal phenomenon, a golem decomposing before one’s eyes. The most devastating portrait of Rudy in oily disarray was a New York magazine profile by Olivia Nuzzi, on his return from Ukraine.

She described an early afternoon car ride with him to the restaurant at the Mark, a five-star Upper East Side hotel. Sitting in the back seat with her, his fly unzipped, saliva dripping down his chin, he sang her an aria from Rigoletto, fumbled with three cellphones, and tossed around conspiracy theories linking George Soros to the media and Marie Yovanovitch. ‘Soros is hardly a Jew,’ he said of the Jewish philanthropist. ‘I’m more of a Jew than Soros is.’

Some remarks defy explication.

After a matchless record of wretched failure as Trump’s private envoy and personal lawyer, Giuliani put in for a Presidential Medal of Freedom – a well-deserved acknowledgment of his valiant service to undermining democracy.

He didn’t get his Wizard of Oz medal, or the pre-emptive pardon some of Trump’s rat pack received, and was stiffed on the legal fees he was owed by the former president. ‘He was staring at millions of dollars in legal bills, a cash drain so serious that he feared bankruptcy. Donald Trump, for whom he had sacrificed so much, was not offering to return the favor.’

Giuliani takes a phone call after being interviewed by the House of Representatives about his role in the January 6 attacks.

He got, as we say in New York, bupkes. Less than bupkes. Negative bupkis. Giuliani so sullied his legacy that the major television networks declined to interview him on the twentieth anniversary of 9/11, denying him his moment in the memorial spotlight.

In the closing pages of his book, Kirtzman tries to eyedrop a little pathos into Giuliani’s predicament, charitably ending with a quote from one of his few remaining admirers, a 23-year-old former assistant called Christianné Allen. But it’s hard to feel sorry for a man so stupid, blind and indifferent to the damage he’s done. He’s long past poignancy.

The book’s subtitle – ‘The Rise and Tragic Fall of America’s Mayor’ – is loftier than he deserves. This may be classified as a political biography, but it reads more like an autopsy report from the wax museum. All that’s left to do is to mop up the drips.

Giuliani: The Rise and Tragic Fall of America’s Mayor, by Andrew Kirtzman, is available now

James Wolcott is a Columnist for AIR MAIL. He is the author of several books, including the memoir Lucking Out: My Life Getting Down and Semi-Dirty in the Seventies and Critical Mass, a collection of his essays and reviews