Review: The tragedy and farce of Rudy Giuliani, explained

On the shelf

Giuliani: The Rise and Tragic Fall of the American Mayor

By Andrew Kirtzman
Simon & Schuster: 480 pages, $30

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After Rudolph W. Giuliani married his third wife in 2003, he left her notes when he went to work in the morning. He would write “I love you” at the end and then draw a heart around the words.

He also kept a baseball bat under the bed, just in case. He may have been at the height of his fame, dividing his time between estates in the Hamptons, Palm Beach, and Manhattan, but he was still the son of a bone-crushing loan shark enforcer in Brooklyn.

It’s that mix of vulnerability, neediness, paranoia, and hostility that resonates in Giuliani: The Rise and Tragic Fall of America’s Mayor, a new biography by Andrew Kirtzman. The book, out this week, shatters the myth and caricature that has too often defined Giuliani, the former mayor of New York City who more recently has served as the wingman for President Trump’s assault on democracy.

Rudy Giuliani

Rudy Giuliani at Four Seasons Total Landscaping on November 7, 2020 in his darkest hour. Andrew Kirtzman connects the former mayor’s ups and downs in a new bio.

(John Minchillo/Associated Press)

As a former TV reporter for NY1, Kirtzman knows the man better than the pundits, who have often scratched their heads over the Giuliani they thought they knew. In his first book about him, Emperor of the City, originally published in 2000, Kirtzman wrote, “I thought of him as a big man and a mean one, a visionary and an opportunist, a shifting leader and an intolerant one .”

His assessment is now only grimmer. If Giuliani’s story is a tragedy, Kirtzman argues that it was self-inflicted through a combination of alcohol, hypocrisy, and a boundless need for attention.

"Giuliani: The Rise and Tragic Fall of the American Mayor" by Andrew Kirtzman

Despite being one of the country’s best-known political figures, the ex-mayor’s life is often summed up in two snapshots. The first is Giuliani, caked in ash from the destruction of the World Trade Center on 9/11, shepherding his traumatized city through its darkest moment. The second is in a sweltering room at the Republican National Committee headquarters, hair color streaming down the sides of his face as he develops conspiracy theories about the election being stolen from Trump.

The greatest service of Kirtzman’s book is to connect the dots between these dots, separated by nearly two decades.

“When he left the mayoral office, he lost track of the ardent mission that had propelled him throughout his career, which was to wield power and impose his views on right and wrong,” Kirtzman writes.

With Giuliani busy making money being a consultant for companies like OxyContin maker Purdue Pharma, his third marriage to Judith Nathan was no sanctuary. She feuded with Giuliani’s staff, most memorably over a selection of hats chosen for her to wear at Buckingham Palace when Giuliani received the Knighthood of Honor in 2002.

Nathan also played on Giuliani’s insecurities as they argued. “Rudy said to me, ‘Who do you think you are?'” Nathan recalled. She would reply, “Who the hell are you, your dad was in Sing Sing,” a reference to the notorious New York jail where the elder Giuliani served time after his arrest for his role in an armed robbery.

Giuliani ran for president in 2008 and got into the polls in the Republican primary, but it was a disaster. Kirtzman writes that “showing up with just a single delegate was a disastrous end to a lifelong ambition”. Nathan said she “couldn’t get him out of bed,” and they moved to Palm Beach, Florida. He spent his days rummaging around his in-laws’ apartment and smoking cigars on the terrace in his bathrobe.

Andrew Kirtzman, author of "Giuliani: The Rise and Tragic Fall of the American Major," has been reporting on his subject for decades.

Andrew Kirtzman, author of “Giuliani: The Rise and Tragic Fall of America’s Major,” has reported on his subject for decades.

(Kyle Fromman)

Back then, in one of Giuliani’s lowest moments, his relationship with Trump deepened. After photographers found Giuliani in the apartment, he moved to Mar-a-Lago. Kirtzman writes that he lived with Nathan in a bungalow across the street and used a network of tunnels under the property to stay out of sight.

“Donald kept our secret,” Nathan said.

Giuliani and Trump had known each other for years, and Giuliani had been something of a proto-Trump as mayor, with “an instinctive ability to hit the outrage button at a whim.”

Indeed, the law-and-order mayor lived and ruled in a constant state of chaos. In 1999 and 2000, Giuliani stoked racial tension after plainclothes police officers killed a West African immigrant, was battling prostate cancer, announced he was divorcing his second wife, and then decided he didn’t want to serve in the US Senate would run against Hillary Clinton.

Rudy Giuliani, left, with Donald Trump

Rudy Giuliani, left, with Donald Trump during a skit performed at a then-mayor’s roast in 2000.

(Kyle Fromman)

Though his tenure as mayor was deeply disputed, his international standing exploded after the September 11 attacks. Kirtzman spent that morning with the mayor as they fled for their lives in lower Manhattan. He doesn’t miss out on the bursts of inspiration of his motif. In a moment of terror, Giuliani found words to comfort and shake up the city and country. But Kirtzman argues that Giuliani also used his heroic story as a shield against accountability. His government had failed to prepare for possible attacks, and communication problems hampered the response.

“His appearance on 9/11 was a carpet of inspired leadership and fatal mistakes,” writes Kirtzman. “The public saw only part of the picture on that horrific day; the rest were shrouded in admiration for years.”

Giuliani’s service to Trump undermined that. He helped defend the former president during the Russia probe, then burned his credibility in a daring quest to smear Joe Biden in Ukraine. The result was Trump’s first impeachment trial.

After Trump lost the election, Giuliani fueled his complaints and lies about voter fraud. Four days after the Jan. 6 attack on the US Capitol, Giuliani’s girlfriend wrote a letter to Trump asking for three things for him – payment for legal services, the Medal of Freedom, and a “general pardon.” (It’s unclear whether Giuliani knew of the letter, which Kirtzman says he verified, and may never have reached Trump himself.)

“In a life of crusades, this was his grand finale, and it ended in a crescendo,” writes Kirtzman.

Of course, Giuliani’s final act remains unknown. The New York Times recently reported that he is unlikely to face charges of illegal lobbying on behalf of Ukrainian officials. However, prosecutors in Georgia have described him as the target of a separate criminal investigation into efforts to overthrow the last election.

Maybe Giuliani has to fall further.

Megerian is a White House reporter for the Associated Press and a former Times contributor. Review: The tragedy and farce of Rudy Giuliani, explained

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