On March 16, an undercover cop working a "buy and bust" sting outside a Manhattan cocktail lounge tried to persuade a 26-year-old Haitian-American security guard named Patrick Dorismond to sell him some drugs. Dorismond took offense at the officers' overture. A scuffle erupted, a cop's gun went off, and Dorismond fell to the pavement dead. Amid the news of the fourth police shooting of an unarmed black man in the city in 13 months, Giuliani and his police commissioner, Howard Safir, released the dead man's sealed juvenile record to discredit him. The victim "wasn't an altar boy," the mayor said.
In fact, Dorismond had, literally, been an altar boy. He had even attended the same Catholic high school as Giuliani. As Time's Margaret Carlson would write, "Giuliani may want to consider saying he's sorry and letting Patrick Dorismond rest in peace." Instead, Giuliani said he had no regrets and had handled the matter "appropriately." Within days of the shooting and Giuliani's response, polls indicated that his electoral support within New York City, the advantage he'd enjoyed over any other potential GOP Senate candidate, had begun to collapse among two key groups, Latinos and Jews. At the start of the month, a Zogby poll had still shown Giuliani in the lead statewide; by March 25, another Zogby poll had Clinton 3 points ahead.
An early April New York Times poll gave Clinton an even larger lead, 8 points. Giuliani remained deadlocked with her upstate -- but then he scrapped an upstate campaign swing in order to attend the Yankees home opener, blowing off 400 ticket-holders to a "Women for Giuliani" luncheon in Rochester. Giuliani was unapologetic, telling reporters at the ballpark that he'd ignored the advice of his advisors so that he could do what he loved best. Clinton popped up outside a diner in Rochester, a portable microphone in her hand. "Well, I'm happy to be here," she said. "I have enjoyed coming to the Rochester area talking about the issues."
In a sense, it was all a replay of 1998 and early 1999, before either candidate had officially announced. Back then, Hillary had topped the polls because New Yorkers were, for a time, sympathetic to her and sick of Rudy. Throughout the state, voters had channeled their weariness with the GOP-dominated Congress' impeachment of President Clinton into support for his wife; at the same time, New York City voters expressed their irritation with Giuliani's insensitive handling of another police shooting -- the death of Amadou Diallo -- by withholding their support for him. Hillary as victim and Rudy as bully had meant a fleeting lead in the polls for the Democrat, one that evaporated once memories of Lewinsky and Diallo became less vivid. A year later, Rudy was again making Clinton the victim and himself the bully, and again helping his opponent.
After Dorismond, the bad news never stopped for Rudy. On April 27 he announced that he'd been diagnosed with early-stage prostate cancer. Though he resumed campaigning within days of surgery, expressing eagerness to return to the trail, the New York Post soon published a photograph of the married father of two children standing next to a woman the tabloid described as a "Mystery Brunch Pal."
At the same time, the New York Conservative Party began to make good on its threat to back a third-party bid rather than endorse Giuliani. Former Rep. Joseph DioGuardi announced that he was seeking the nomination on the Conservative line, and party chair Mike Long called him "the right candidate." Just as in the present election cycle, when social conservatives have hinted they may boycott the candidacy of the pro-choice Giuliani, Long had been hinting throughout the 2000 Senate race that Giuliani would have to change his stand on abortion and several other litmus-test issues or forgo the Conservative Party's endorsement. No Republican had won statewide office in New York in more than two decades without appearing on the Conservative Party ballot line as well. In some cases, the endorsement had been worth 200,000 votes. Long's disenchantment was also personal; the endorsement had been withheld, at least in part, because of Giuliani's abrasive manner. "The mayor," said Long, "just doesn't know how to handle human beings."
Republican power broker Joseph Bruno, the majority leader of the state Senate, was soon pleading with Rudy to straighten out his marriage and focus on defeating Hillary. But by then it was too late. Giuliani was about to give himself the coup de grâce.
As Bruno's comments made headlines, the mayor disclosed at a May 10 press conference that he did indeed have a "very special friend." His secret affair with Judi Nathan had started some 10 months earlier, said Giuliani. By the way, he was also leaving his wife of 16 years, Donna Hanover.
Hanover apparently didn't know that last bit of information was coming. She learned about the dissolution of her marriage on the news. Badly stung, the mother of Giuliani's two children emerged from Gracie Mansion hours later to give her own press conference. Fighting back tears, Hanover accused her husband of conducting another earlier affair with a City Hall aide. He denied it.
After 10 rocky days of deliberation, Giuliani excused himself from the chaos. He dropped out of the race at a packed City Hall press conference on May 20. Giuliani cited his health. His once-promising career in politics looked finished, something he recognized in saying his illness taught him that politics was not the most important thing in his life any longer.
There were only 11 days left before the GOP's state nominating convention. Rep. Rick Lazio, who had never formally left the Senate race despite the party hierarchy's preference for Giuliani, stepped in to accept the Republican nomination.
As Giuliani had self-destructed, the media's conventional wisdom had congealed around the notion that while Clinton was a decent campaigner, she, like her husband, had also proved remarkably lucky in her enemies. When the obscure and inexperienced Lazio replaced Giuliani, however, a few Beltway pundits still tried to frame this as bad news for Hillary. The fact that Lazio was unknown outside Long Island became a threat to Hillary, as did the new GOP candidate's boyish demeanor. He was "baggage-free." "Rick Lazio," wrote one journalist, "could be [Clinton's] worst nightmare."
Lazio, unsurprisingly, began to campaign exactly as Giuliani had back when he was seen as the inevitable victor. Once again, the GOP's Senate candidate made Hillary the issue. Lazio picked up the Giuliani playbook, labeling Clinton a carpetbagger, a panderer, a flip-flopper. For a time, in summer, he made a race of it, but in the end aggression was counterproductive. The congressman's fate was sealed during the first Senate debate on Sept. 13, 2000. Mid-debate, Lazio strode across the stage to confront Clinton, repeatedly demanding that she sign a piece of paper pledging she would renounce the use of soft money in her campaign. The invasion of personal space made Lazio look desperate, adolescent and vaguely creepy. Twice in one race a Republican candidate's attacks on Hillary had provided no net benefit.
Lazio started the race 6 to 9 points behind and ended it 12 points behind. Clinton won comfortably in November, 55 to 43 percent, surviving the most expensive Senate contest in U.S. history. There had been only a narrow band of undecided voters available to her at the beginning of her run, but by Election Day she had brought nearly all of them into her camp.
In 2007, Giuliani is reprising his anti-Hillary routine. He has ripped her "socialist" healthcare plan, her $5,000 baby bonds and her criticism of Gen. David Petraeus' assessment of Iraq. He has revisited Wrigley Field to make fun of her Yankees leanings; he is saying that she has never run ... anything! And he has cast himself as the strongest antidote to Clinton in the Republican field, should she win the Democratic nomination. "He's almost itching to unleash against Hillary," someone associated with his presidential campaign told Salon.
It almost feels like 2000 all over again. Judging by 2000, however, another chorus of "Captain Jack" might not keep Hillary Clinton from her goal.
About the writer
Robert Polner is the editor of "America's Mayor, America's President?: The Strange Career of Rudy Giuliani" (Soft Skull Press, 2007). He is also communications director for the Robert F. Wagner Graduate School of Public Service at New York University.
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