Discover more from The Sword and the Sandwich
The Rise & Fall & Rise & Fall & Rise & Fall of Rudy Giuliani
From America's Mayor to America's Most Wanted
By the time you read this, Rudy Giuliani will have surrendered at the Fulton County jail in Georgia for his role in the racketeering case against Donald Trump. To celebrate this occasion, we’ve put together an archival narrative of Rudy’s rollercoaster career, from crusading prosecutor to common criminal.
The woman cannot believe she’s in the same elevator as Rudolph Giuliani, the Federal prosecutor for Manhattan. “You're Rudolph Giuliani,” she says. “Oh, I can't believe it. You're the one in the papers — with the mob.” She is staring. “Oh, this is a thrill.”
“Frankly,” Giuliani replies, “I'm surprised you're not worried about riding the elevator with me.” It is a line he often uses at speaking engagements. He knows joking about death threats is almost always good for a big laugh.
Heaven’s Hit Man
By Gail Sheehy
Vanity Fair, August 1987
Rudolph Giuliani is the biggest face in New York law enforcement. That bloodless white face with dark steady eyes and goofy haircomb turns up everywhere, like a death mask, announcing the demise of the Mafia, promising punishment for crooked politicians, springing swift and terrible justice on blue-chip Wall Street traders. Most people are still fuzzy on his title—U.S. attorney for the Southern District of New York—but they know his monk's face and his altar-boy lisp. Rudy Giuliani has become a force.
The Toughest Weenie in America
By Philip Weiss
Spy, November 1988
Giuliani was raised in a family with a traditional southern-Italian patriarchy. He was the only child of a forceful father whom he idolized. “The first thing that's important — you respect me,” Harold Giuliani, a bar owner, had told him. I got a sense of how much the son identified with his father at a temple breakfast earlier this year. Giuliani told the audience that he recalled his father saying he enjoyed paying taxes. He went on: “It was only years later and probably after I died that I realized what he meant by that.” I died, he'd said, referring to his father's death, and continued without a pause.
Rudy’s Fall from Grace
By Joe Klein
New York, August 21, 1989
The Photograph is cruel but irresistible, and the Daily News has used it twice now. There's Rudy Giuliani, smiling for a change, holding his young son, An-drew, aloft at a parade in Brooklyn. “It would have been one of the nicest shots of the campaign,” says an aide. “If it weren't for that other detail.” Right. That other detail. A gust of wind has blown back the candidate's carefully arranged hair, revealing ... a totally bald man who looks an awful lot like Rudy Giuliani.
The photo first appeared on July 9, and it immediately became the guilty pleasure of the local political community: Poor Rudy! What else could happen to him? The guy's setting a record for political free-fall, from savior to shme-gegge in three months!
What’s Wrong With Rudy Giuliani?
By Dan Collins
Village Voice, August 29, 1989
Then there was the Donald Trump newspaper ad in which the balding air-shuttle executive talked about his “hate” for muggers and murderers and the need to incinerate the little criminals. Even death penalty–Ninja Ed Koch found this excessive, but Giuliani hailed the ad by the co-chairman of his first big fundraising event as contributing to what he called a “healthy debate.” On the day he announced his candidacy, however, Giuliani traveled to Bishop Loughlin, the Catholic high school in Brooklyn that he attended as a boy, and faced a solidly black and Hispanic student body. Giuliani swiftly distanced himself from “Trump-the-ad” when a black student asked him if he endorsed the hyperactive casino owner’s position. No flapdoodle for this audience.
Rudolph Giuliani and the Color of Politics in New York
By Todd S. Purdum
New York Times Magazine, July 25, 1993
Though he is just 49 years old, Giuliani often seems a striking throwback in New York City's anything-goes atmosphere. It's as if his cultural and psychic sensibilities froze about 1961, the year he left the tutelage of the Christian Brothers at Bishop Loughlin Memorial High School in Brooklyn. This is a man so square that he started an opera club in high school and still refers to his old high-school classmates as “other youngsters”; so corny that he proposed to his current wife at Disney World; so accepting of authority that he says the nuns and brothers who taught him were right to smack him around, because he often deserved it.
By John Taylor
New York, October 11, 1993
In person, Giuliani is surprisingly relaxed, unpretentious, intelligent, and funny, and a central objective of the advertising campaign put together by his media adviser, David Garth, has been to “humanize” Giuliani's image by broadcasting these traits. But Giuliani is also very sharp and very self-confident. As U.S. Attorney for the Southern District of New York, he did not suffer fools gladly. While he has eliminated from his vocabulary much of the legalese that accentuated his crowd-awkward manner in 1989, he still has a prosecutor's unapologetic directness, and even his supporters will admit that he does at times rub some people the wrong way. “He can be abrasive,” says one of the city's Republican politicians.
To Giuliani, that is not necessarily a shortcoming.
Rudy Giuliani is a Colossal Asshole
By Martha Sherrill
Esquire, October 1, 1997
A sign out front says, MEET THE MAYOR, and there’s a picture of Rudy Giuliani smiling his ghoulish public smile, with his cavernous dimples and aspirin-white teeth. The grin is utterly horizontal, a perfect straight line, as though a ruler and a razor together had cut it into his face. Five hundred people have gathered inside the Hebrew Institute of Riverdale in the Bronx, and Giuliani is standing before them, above them, on a stage. He is wearing a black suit. Everything about him is peremptory, except that his shoulders are sort of sad and hunched and his hair, which is gelled or glued down, is cupping his head like a small helmet.
Rudy’s Oval Office Dream
By Mark Jacobson
New York, November 10, 1997
“If I say President Giuliani, what do you say?”
“Oh, man," the smoker said. “Just shoot me now.”
During my multi-borough canvassing on the “Rudy-as-prez” beat, the above was not a wholly unique response. Other replies from people of color included: “It'd be like back in Alabama,” “Slavery days again," “Tyranny,” “That'd be an American moonwalk backwards.” In Flatbush, a karate teacher leveled a steely gaze at me and said, “Rudolph Giuliani is an agent of spiritual chaos...”
The Sword and the Sandwich is a newsletter about serious extremism and equally serious sandwiches. Please consider supporting this work with a paid subscription:
Rudy Giuliani’s White World
By Wayne Barrett
Village Voice, January 26, 1999
All his life Rudy Giuliani has occupied a milky universe — raised in a blanched Nassau suburb, educated at insular Bishop Loughlin High School and Manhattan College, shuttling twice between the colorless cubicles of the Justice Department in Washington and the U.S. Attorney’s Office in Manhattan, practicing law at three mainline firms where not just the shoes were white.
As a kid born in Brooklyn, he rooted for the all-white Yankees while Jackie Robinson crossed the color line at Ebbets Field, just a couple of miles away from his home. He so craves the familiar he married his own cousin.
By Wayne Barrett
Village Voice, July 4, 2000
After a year and a half at Sing Sing State Prison, Harold Giuliani was released on September 24, 1935. A year later, while on parole, he married his long-courted sweetheart, Helen D’Avanzo, at St. Francis of Assisi Church in Brooklyn. On May 5, 1939, more than two years after he and his new wife had moved into a house they shared with her mother, he completed his parole.
It took the Giulianis six years and one miscarriage to have a baby. “Helen had the miscarriage early in the marriage,” recalled Anna D’Avanzo, one of Helen’s sisters-in-law. “The next time I saw her, she was crying. Harold always looked at the good side, ‘We’ll have another one.’ ” Eventually, Harold was right. On Sunday, May 28, 1944, Helen, age 35, gave birth to her long-awaited and only child, Rudolph William Louis Giuliani.
By James Traub
New York Times Magazine, February 11, 2001
He tried, notoriously, to defund the Brooklyn Museum of Art as punishment for showing an exhibition he deemed offensive. In his own realm, he has locked the gates to City Hall Park, establishing a security system inside a big white tent that appears to be modeled on the White House. He banned news conferences on the steps of City Hall, though that was overturned by a judge — as was the attempt to bring the Brooklyn Museum to heel.
Mayor of the Moment
New York Times, September 14, 2001
Whatever he has been before or will be in the future, Mayor Rudolph Giuliani became the leader New York City needed in its worst moment. With little rhetoric and less poetry, he consoled a stunned populace trying to make sense through the smoke and beyond the jagged skyline. With phrases aimed at people rather than the history books, Mr. Giuliani rallied a city to “go back to normal,” to start going to restaurants, to try to work or go to school as a way to show its unbroken spirit.
Person of The Year 2001: Rudy Giuliani
By Nancy Gibbs
Time, December 31, 2001
“Show me a hero, and I will write you a tragedy,” said F. Scott Fitzgerald. On the morning of Sept. 11, primary day in New York City, Rudy Giuliani was paddling along with all the other lame ducks into oblivion… After abandoning Gracie Mansion, his marriage in flames, he was camping out with friends on the Upper East Side, and now it was time to choose his successor, and the end was in sight.
The end was, in fact, just a few blocks away. Having raced to the scene at the first news of the attacks, Giuliani was nearly buried alive. In the hours that followed, he had to lock parts of the city down and break others open, create a makeshift command center and a temporary morgue, find a million pairs of gloves and dust masks and respirators, throw up protections against another attack, tame the mobs that might go looking for vengeance and somehow persuade the rest of the city that it had not just been fatally shot through the heart.
America’s Mayor Goes to America
By Matt Bai
New York Times Magazine, September 9, 2007
So you wouldn’t want to have a beer with me, Rudy seems to be saying. So even my own kids don’t want to have a beer with me. But whom do you really want staring down the terrorists — me, or one of these other guys? Do you want someone squeezable, or would you rather hire the single-minded enforcer who had the testicular fortitude to tame New York?
How the Giuliani Method May Defeat Him
By Elizabeth Kolbert
New Yorker, December 30, 2007
For all the reasons that he mentions — the fall in crime, the drop in the welfare rolls, the general change of mood in the city — Giuliani was an unusually accomplished mayor. What made him remarkable was that he didn’t settle for these achievements. In addition to muggers and drug dealers, he eventually went after cabdrivers, jaywalkers, hot-dog venders, street artists, museum curators, strippers, and people who were just insufficiently civil — in short, practically everyone in New York. The same mayor who urged calm on September 11th two weeks later sought — unsuccessfully — to declare a sort of municipal state of emergency in order to extend his term in office.
A Tale of Two Giulianis
Vanity Fair, January 2008
On a late-spring day in 2001, Rudy Giuliani's divorce lawyer stood on the steps of the New York State Supreme Court Building and told reporters the shocking truth. His client, the mayor of the city — beleaguered by an angry wife who wanted more money — had only $7,000 to his name…
Three months later came 9/11.
How Rudy Giuliani Turned Into Trump’s Clown
By Jeffrey Toobin
New Yorker, September 3, 2018
This version of Giuliani isn’t new; Trump has merely tapped into tendencies that have been evident all along. Trump learned about law and politics from his mentor Roy Cohn, the notorious sidekick to Joseph McCarthy who, as a lawyer in New York, became a legendary brawler and used the media to bash adversaries. In the early months of his Presidency, as Mueller’s investigation was getting under way, Trump is said to have raged, “Where’s my Roy Cohn?” In Giuliani, the President has found him.
The Fog of Rudy
By Jonathan Mahler
New York Times Magazine, January 15, 2020
To be a larger-than-life mayor doesn’t require money. But to be a larger-than-life ex-mayor requires a lot of it. Giuliani had always been fixated on power, and with his political career on pause during the Bush years, he needed money to stay relevant. ‘‘He became extremely materialistic and almost money-grubbing,’’ a member of Giuliani’s inner circle at the time told me. ‘‘He was always a narcissist who demanded unflinching loyalty. After 9/11, that was magnified a bit, but the mercenary quality of his personality really emerged after 9/11.’’