When Rudy met Hillary

Rudy Giuliani markets himself as the Republican with the best shot at beating Hillary Clinton next fall. But the first time the pair faced off, that's not how it worked out.

By Rob Polner

Read more: Rudy Giuliani, Hillary Rodham Clinton, Politics, Rick Lazio, News, 2008 election

Reuters/Ray Stubblebine and AP Photo/Stephen Chernin

Hillary Rodham Clinton (left) announces her candidacy for the U.S. Senate on Feb. 6, 2000. Later that week, Rudy Giuliani announces his bid.

Nov. 27, 2007 | On Feb. 6, 2000, the day Hillary Clinton officially announced her bid to become the next senator from New York, her advance team at a venue in suburban Westchester County was supposed to cue up the Billy Joel ballad "New York State of Mind" before she took the stage. Instead, as the crowd waited for Clinton to hit her mark, an aide accidentally broadcast Joel's "Captain Jack," a song about a Long Island drug dealer, complete with references to heroin and masturbation.

The next morning, Clinton's Republican rival for the Senate seat put her on trial at a press conference in lower Manhattan. Sounding like the federal prosecutor he once was, New York Mayor Rudy Giuliani read aloud a political indictment, the lyrics to "Captain Jack."

"'But Captain Jack will get you high tonight,'" Giuliani recited from a paper in his hand, "'and take you to your special island. Captain Jack will get you by tonight ... just a little push and you'll be smiling.'" Then he raised his eyes to address the assembled media. "I think the message that got out by mistake was, 'Let's say yes to drugs.' I think it's a very, very dangerous message."

Meanwhile, Hillary Clinton had already flown off to Buffalo, where she trudged through the snow and talked about jobs and economic recovery. By that November, Clinton was the senator-elect from New York, and Giuliani's political career seemed all but kaput.

The traditional narrative of the 2000 Senate race, the first time Hillary Clinton and Rudy Giuliani faced each other in an election, is that Giuliani was forced to drop out of the race in May because of the sudden emergence of personal issues. Between prostate cancer and an impending divorce from his second wife, the erstwhile front-runner was, allegedly, no longer a viable candidate.

Perhaps the combination of serious illness and an admitted affair would've been enough, in and of themselves, to sink any candidate's Senate campaign. But in reality, prior to either revelation, Rudy Giuliani was already losing. Hillary Clinton's relentless ground game had slowly eaten away at his lead, but Rudy had done the bulk of the damage himself. In early 2000, polls showed Rudy beating Hillary. Then Hillary began her long march through the snow, and Rudy reminded New York voters again and again what an abrasive figure he could be. The more he made Clinton appear to be a victim, and himself a bully, the better Clinton fared.

Eight years later, the early polling on a potential Rudy-Hillary match-up looks oddly familiar. Would a presidential race between Hillary and Rudy also be a rerun?

The first Rudy-Hillary showdown began to loom in 1998. Giuliani had won a second four years as mayor by a landslide the year before, his last allowable term under law. In the summer of 1998, the mayor, who had seldom left the city during his first term, started hopscotching around the country in what looked like an attempt to burnish his GOP credentials ahead of a run for higher office. There were meetings and photo ops with presidential hopefuls Sen. John McCain of Arizona and Gov. George W. Bush of Texas and with a host of county- and state-level GOP leaders. He apologized for his endorsement of Democrat Mario Cuomo for New York governor in 1994, did imitations from "The Godfather," and regaled GOPers from Pennsylvania to California with jokes about the city he governed -- and Hillary Clinton.

By then there was already speculation that 71-year-old New York Democrat Daniel Patrick Moynihan would not be seeking another term as senator, and that two of the likely contenders to be his successor were Giuliani and Clinton. Days after the midterm elections of November 1998, Moynihan made his retirement official. Soon the field was cleared for Clinton and Giuliani, though a Long Island congressman named Rick Lazio refused to get the message and continued to believe that he was in contention for the Republican nomination.

From the beginning, the 2000 Senate battle between Giuliani and Clinton had many of the same elements as does the potential 2008 presidential match-up. Clinton would try to protect the Democratic base and swing enough of the narrow band of undecided voters to her side to prevail. Giuliani would start with a decided advantage: Much of the electorate already knew his opponent and disliked her. Hillary Clinton had never even lived in the state she wanted to serve. Giuliani would use Clinton's unpopularity to his benefit and also veer rightward to convince skeptical conservatives that despite his socially liberal record as mayor -- and the fact that his views on many issues were hard to distinguish from Clinton's -- he was still a real Republican. The oddsmakers favored Rudy.

Clinton led Giuliani in polls from late 1998 and early 1999, but by midsummer the two were in a statistical tie. On Tuesday, July 6, 1999, Clinton gave her campaign an unofficial soft launch. She announced that she had formed an exploratory committee for a Senate run. That weekend she began a so-called listening tour of New York state from Dan Moynihan's 900-acre farm in Pindars Corners, a one-traffic-light hamlet 70 miles west of Albany. A sea of news cameras captured the moment as Moynihan christened the launch by walking Clinton to the edge of his property and bidding her good luck. "I think I have some real work to do," Clinton said, "to get out and listen and learn from the people of New York and demonstrate that what I'm for is maybe as important, if not more important, than where I'm from."

Giuliani, meanwhile, hit the ground punching. He made mockery of his opponent a campaign tactic from the start. In June, prior to Clinton's soft launch, he had attended a Chicago Cubs game at Wrigley Field and ridiculed Clinton's recent account of nurturing a longtime affinity for the Yankees despite growing up a Cubs fan in Chicago. In July, a week after Hillary's Pindars Corners photo op, Giuliani trekked to Little Rock, Ark., to raise funds for his own Senate run. From there, he ordered the state flag of Arkansas flown outside New York's City Hall to thank his Republican hosts for their hospitality -- and to tweak the former first lady of Arkansas as a reverse carpetbagger. "Maybe I'll run for governor of Arkansas," Giuliani joked more than once during his Little Rock trip.

Clinton had to establish a residence in New York so she could qualify for the ballot under state law, but she and her husband hadn't even started shopping for a home. They would later move into a $1.5 million Westchester County house. But Hillary Clinton had already ceded the "carpetbagger" argument to Giuliani. At Moynihan's farm she had told the assembled press that the tag was "a fair one." And "carpetbagger" was never a debilitating accusation in New York anyway. Older voters remembered that Robert F. Kennedy had been a "carpetbagger" before beating incumbent Republican Kenneth Keating in 1964 to become the junior senator from New York.

Clinton's Listening Tour would test the political reporters' attention spans and physical endurance as she led them, in slow motion, though all 62 New York counties. The earnest student of the state addressed small groups of voters at each stop about such perennial upstate issues as dairy price supports, air fares, college tuition, and the exodus of college graduates in search of work. She appeared to benefit from low expectations. Just by showing up without horns on her head in the Republican hinterland -- a bona fide national celebrity to boot -- she managed to mollify some voters who had been trained to hate her.

Video: Rudy recites "Captain Jack"

Next page: "It's only February and it's come to this"