The “toxic marriage” was to Judith Nathan, a sales manager at Bristol Myers Squibb, whom he met in a cigar lounge on the Upper East Side in 1999 and who became his third wife. Kirtzman says that she was loathed by everyone in Giuliani’s circle, regarded as “deeply manipulative and obsessed with status and money.” As Giuliani’s former chief of staff Tony Carbonetti explained the matter to Kirtzman, “She’s a horrible human being.”
In Kirtzman’s account, Judith was demanding, questioned everyone’s loyalty, and seems to have had a death grip on her man, who was terrified of her displeasure. Giuliani’s children, Caroline and Andrew, stopped speaking to him for years. (Andrew later became a golfing buddy of Trump’s, worked in the Trump White House, and, this year, ran for the Republican nomination for governor of New York, with his father’s support. Despite the name recognition, he lost by twenty points.) The couple’s divorce, in 2019, was bitterly contested.
And alcohol does seem to be part of the story. Giuliani was always a red-meat, Scotch-and-cigars kind of person, but the drinking appears to have become serious after the debacle of his Presidential run, in 2008. That campaign was right out of the “New York mayor bombs on the big stage” playbook. In November, 2006, Giuliani was ranked the most popular politician in the country, and he went into the Republican primaries as the clear front-runner. In July, 2007, he was eighteen points ahead in the polls.
Then the New York curse kicked in. In November, Giuliani’s pal and business partner Bernard Kerik, whom he had named police commissioner (despite the fact that Kerik had never finished high school), was indicted on sixteen counts of corruption. (Kerik later pleaded guilty to some of the charges and served three years in prison. In 2020, he was pardoned by President Trump. In the Trump gift shop, pardons are cheap.)
There was also a brief to-do about the fact that Giuliani Partners had worked for the government of Qatar, a nation that had given haven to Khalid Sheikh Mohammed, who was named the principal architect of the September 11th attacks. And it came out that, while Giuliani was mayor, he had used the budgets of obscure city agencies like the Office for People with Disabilities to cover travel expenses, which some people connected to secret trysts he was having in the Hamptons.
Giuliani’s affair with Judith, while he was still married to his second wife, Donna Hanover, did not sit well with social conservatives in the Party’s base. (Giuliani had had his first marriage, to Regina Peruggi, annulled on the ground that they were second cousins. He did not inform her that he was doing this.) Nor were conservatives happy with his relatively liberal—that is, New Yorker—views on issues like gun control and abortion. A man who prospered through bluntness, he struggled to spin his positions rightward. In January, he finished sixth in the Iowa caucuses and fourth in the New Hampshire primary. He got two per cent of the vote in South Carolina.
Florida, as it had for John Lindsay, dealt the fatal blow. The campaign had doubled down in the state (those New York retirees!), but Giuliani took only fifteen per cent of the vote, good for third place. He dropped out of the race, his campaign having burned through sixty million dollars and ended up four million in debt. He had one delegate. Giuliani’s career in national politics was over before it had properly begun. He and Judith were taken in by an old friend, who let them stay at his estate, Mar-a-Lago. No one else would have them.
In the years that followed, Giuliani drank heavily. “He was always falling shitfaced somewhere,” Judith Giuliani told Kirtzman. (She denies saying it.) On Election Day, 2020, Giuliani—oddly, but presumably he was being compensated—did a thirty-minute show for RT, a Russian state television network, where he told his listeners that Hunter Biden served as Joe Biden’s bagman, collecting bribes for him. That evening, Giuliani showed up at the White House.
He was “definitely intoxicated,” Jason Miller, a Trump adviser, told the House January 6th Committee, when he insisted on seeing the President. And that, apparently, was when he advised Trump to announce that he was not conceding, because the election had been stolen—the first step on the road to January 6th and a second impeachment. Kirtzman says that we can be thankful for one thing Giuliani did in Trump’s post-election madhouse, which was to oppose the recommendation to call in the military and confiscate voting machines.
It’s natural when trying to understand a crash-and-burn peripeteia as spectacular as Giuliani’s to wonder whether he was all that great to begin with. How far did he really fall? Kirtzman, who covered Giuliani’s mayoralty as a reporter and as a host of “Inside City Hall,” on the news channel NY1, and who was with him on September 11th—this is actually his second Giuliani biography—reviews the entire career in this revisionist spirit. There’s new reporting and interviews; still, much of the critique covers familiar ground. The lapses and excesses had always been there to see.
Because he governed the city during a period of recovery, and because his comportment on September 11th was exemplary, Giuliani came to be regarded as a paragon of leadership. This was not unjust. A lot of political success is timing and luck. If the city’s economy or crime rate had gone south owing to circumstances beyond his control, he would have had to take the blame.
In a way, the most significant thing Giuliani did for New York City was to get elected. He ran against the Great Society liberalism that had dominated city politics since the Lindsay administration and that had developed a kind of institutional sclerosis, with the competing demands of various interest groups making governance almost impossible. When Giuliani came to office, more than a million people—a third of the workforce—held publicly funded government, health, and human-services jobs. Most of those people were unionized, and the bureaucracy was essentially feudal.
There was little transparency. Just by giving the impression of clear leadership, Giuliani changed the political culture of the city—something that became vividly apparent when he left office and was replaced not (as many expected) by Mark Green, the city’s public advocate, who was taken, fairly or not, as the representative of the old liberal order, but by a businessman, Mike Bloomberg.
The standard story of Giuliani’s mayoral career credits him with reducing crime and restoring fiscal sanity to city government. And the city did change dramatically on his watch. When he first ran for mayor, in 1989, nearly every municipal office in the city was held by a Democrat, and Democrats had a five-to-one advantage over Republicans in voter registration. But for the middle class the quality of life was deteriorating. The city was still struggling to balance the budget after its near-bankruptcy in 1975; there were almost two thousand murders a year; public spaces were occupied by drug dealers and homeless people. Times Square was a den of iniquity; you could not go into Bryant Park. The night air was filled with the sound of car alarms. People taped signs to the windows of their cars: “No Radio.”