When Rudy met Hillary

Her opponent was spending his time tacking to the right. In September, Giuliani used his mayoral bully pulpit (and the city's legal department) to attack the Brooklyn Museum for an exhibition featuring a contemporary artist's elephant-dung-dappled painting of the Virgin Mary. In a string of angry photo ops, the mayor termed the exhibition "anti-Catholic" and "sick," stirring protests and counter-protests and fomenting a long-lived media furor. While his patently unconstitutional attempt to punish the museum died in the courts, the controversy was a P.R. boon for a Senate campaign in a state that is 40 percent Catholic.

Giuliani also got some unsolicited help with another major New York constituency in November, when Clinton managed to offend one of the Democratic Party's largest and most reliable voting blocs. The New York Post and other media outlets pounced when Clinton, during a presidential visit to the West Bank, sat in silence as Yasser Arafat's wife accused Israel of causing cancer among Palestinians through the use of toxic gas. Cameras caught the first lady kissing Suha Arafat on both cheeks after the speech. While Clinton rebuked the wife of the Palestinian leader the next day, saying a poor translation had left her unaware of what Mrs. Arafat had really said, many Jewish leaders back in New York sounded less than reassured. Giuliani didn't miss the opportunity to blast Clinton in the media.

Money, too, was easy-come for Giuliani. In January 2000, he sent out an eight-page fundraising letter aimed at conservatives in the American heartland. The handiwork of right-wing direct-mail expert Richard Viguerie, the mayor's solicitation raised the specter of a world where Hillary held sway, inhabited by "liberal judges who have prevented schools from posting the Ten Commandments," by ACLU-countenanced attacks on prayer in schools, and by resistance to the kinds of faith-based social services championed by GOP presidential contender George W. Bush. Giuliani's own words in the letter were measured: "I think America needs more faith and more respect for religious traditions ... not less."

Even eight years ago, when Clinton had yet to hold any elective office, Giuliani was able to raise millions by invoking the possibility of Hillary Clinton in the Oval Office. His candidacy was a sacred cause for out-of-state conservatives who believed that Clinton's Senate campaign was only the test run for a White House bid. Howard Ruff, a Utah financial advisor, formed Ruffpac to solicit donations from Hillary haters nationwide. ("It's a lot easier to kill a 12-inch snake than a 12-foot cobra," he told MSNBC's Chris Matthews during an interview on "Hardball." Matthews, for some reason, responded by helping Ruff hone his rhetoric. "You want to destroy the missile in its silo," said Matthews, "which makes sense to me."). At least 40 percent of Republican campaign funds would come from out-of-state Hillary haters in the 2000 Senate race, helping Giuliani outraise Clinton by 50 percent.

As the new year dawned, Giuliani had become the front-runner. Most polls favored him. In early January, a Marist Poll put him 9 points ahead of Clinton, 49 to 40, and gave him a 61 percent favorability rating. Giuliani also had 42 percent support in New York City, which accounts for about one-third of all statewide votes. The city has long been heavily Democratic, while Republicans, at least eight years ago, could still expect majorities in the suburbs and upstate. But in the city, Giuliani was polling far above the 30 to 35 percent threshold that a Republican for statewide office needed to win. Clinton was on her heels on her party's home turf.

The pundits echoed the polls. "Well, you know what's missing in her campaign?" said Matthews on "Hardball" on Jan. 11, 2000. "I mean, I hate to use the phrase, but there's a phrase like 'white basketball': It's simply going down the court and shooting the basket like a machine. No style, no pizazz, no grace."

"She's had a pretty terrible six months from the time she started coming into the state in July [1999] through the end of the year," agreed liberal journalist Michael Tomasky, then at New York magazine. On the same "Hardball" segment, Fred Dicker of the conservative New York Post dismissed Clinton's chances: "She's in a mode now where she's merely reinforcing already existing prejudgments." Dicker said he thought Giuliani's position was even stronger than the polls indicated.

Still, as Tomasky noted, the numbers had stopped moving in Giuliani's direction. The race seemed to be frozen as solid as the upstate terrain. Then, slowly, the race begin to shift.

Post 9/11, it may be hard for many outside New York to remember that city residents had started to tire of their mayor by 2000, as the end of Giuliani's second term neared. Giuliani's habit of hurling poison darts at Clinton was a reminder to New Yorkers of his appetite for confrontation and his need to belittle opponents. The Clinton operation stuck doggedly to discussing local issues at one campaign stop after another. Hillary would make 30 dutiful visits upstate between July 1999 and mid-February 2000. Giuliani trekked upstate much less frequently, and usually confined himself to city-centered themes and his mayoral record on crime and welfare cuts. The mayor also continued to paint Clinton as a panderer and part of the "liberal elite."

But all of his potshots failed to make a dent in the 10 percent sliver of undecided voters on which the outcome of the election appeared to depend. By January it was clear that Rudy's upstate advertising had not driven Hillary's numbers down or his own numbers up, and polls showed that the carpetbagger charge, never very wounding, had lost much of its power. Clinton ground out yardage little by little and hoped Rudy would beat himself by being, well, himself.

That's what Giuliani was doing on Feb. 7, when he read the lyrics to "Captain Jack" aloud at City Hall. If it was not the turning point in the campaign -- and perhaps it was, because Hillary would pull even with Rudy in some polls within three weeks -- it was at least emblematic of what the coming months would bring.

After Hillary's campaign officially launched on Feb. 6 with its embarrassing, but trivial, musical gaffe, Matt Drudge linked to her use of "Captain Jack" on his Web site. Giuliani operatives contacted reporters early the next morning, telling them to look at Drudge's site, and faxing them an outraged press release from William Donohue of the right-wing Catholic League. Reporters were prepped to ask Giuliani about the Billy Joel song.

At his City Hall press conference, after reading the lyrics aloud, Giuliani professed outrage. "Can you imagine," he asked, "if George Bush had held an event and right before the event a song was played that said, Let's say yes to drugs, let's glorify drugs, let's glorify pot?" He said there was a possibility the choice of songs had been intentional and wasn't just the product of a snafu. "It means that people of that ilk and that ideology are around you."

But the response to Giuliani's gambit, at least in New York City, might not have been what the candidate desired. On the local NBC TV affiliate, political reporter Jay DeDapper betrayed disdain as he explained how the Giuliani campaign had contacted local journalists, trying to interest them in the supposed controversy. "It's only February and it's come to this," said DeDapper, on air. At the end of the week, Daily News columnist Michael Kramer, no Clinton fan, awarded "Round 1" to Hillary, and said Rudy was the loser because he was "on one of his famous, petulant tears." Kramer cited the "Captain Jack" incident. "The mayor's rant," he said, "was petty and bullying." Kramer also slammed Giuliani for filling upstate talk-radio airwaves with "over-the-top" anti-Hillary commentary. Clinton continued to march through the snow.

By March 2, at least in a Siena College poll, the candidates were tied, 42 to 42. External events kept breaking Clinton's way. A jury acquitted the police of murder in the death of Amadou Diallo. George Bush became the all-but-certain Republican nominee for president. Both developments seemed to scare a few Democrats back into Hillary's column. Journalists began to describe Clinton as a greatly improved, dogged campaigner, and they noticed that she was closing in on 50 percent upstate. Democrat Chuck Schumer had hit that magic number when he knocked incumbent Republican Al D'Amato out of the Senate two years earlier. And then, with the race neck and neck, the mayor handed Clinton the lead. He did it not by attacking her or another politician, but by impugning the memory of a previously unknown resident of his city.

Next page: Giuliani was about to give himself the coup de grâce