Clinton vs. Giuliani, The Sequel?

Even by the larger-than-life standards of New York politics, the campaign to retire Sen. Daniel Patrick Moynihan's open seat in 2000 was a monumental battle.

When Hillary Clinton — who made history as the first former first lady to run for public office, and Rudy Giuliani, New York City's mayor and former prosecutor who'd brought down the mob — both ran for the seat, it was the most exciting race in decades.

The equivalent of Godzilla vs. King Kong or Ali vs. Frazier, it was a heavyweight fight that never made it past the first few rounds, leaving political junkies hanging with frustrated anticipation.

The much anticipated showdown, with polls showing a virtual dead heat, was called off when Giuliani dropped out of the race May 19, 2000, when he learned he had prostate cancer. Clinton went on to easily beat Rick Lazio, a weak candidate, who was the only viable Republican remaining in the field.

So, for New Yorkers, the current presidential campaign, with Giuliani and Clinton running at the front of the pack, inspires a strong sense of deja vu, the long-awaited sequel to a classic feud.

"This is the unfinished fight that we didn't have in 2000," says Doug Muzzio, a professor of public affairs at New York's Baruch College. "For the last couple of weeks in that race, they were in a virtual dead heat. This time around, it looks like they will win their party primaries and we'll get that showdown."

Political consultant George Arzt remembers that contest well. "Everyone looked forward to the Senate race — it would have been a bruising race," he says. "Now we're getting the postponed race. If the polls continue like this, it's going to be a brass-knuckled fight."

And just like in the movies, this time the combatants are bigger and stronger.

Compared to their iconic status today, the 2000-era Clinton and Giuliani had significant weaknesses. At the time, Clinton was an untested quantity, pitied by many for her role as the dutiful wife forced to endure her husband's infidelity, and reviled by many conservatives.

Giuliani was a lame duck mayor whose greatest achievements — slashing the crime rate and taming New York — were behind him, and New Yorkers had grown tired of his ornery nature and were ready for a change.

Over the past seven years, Clinton has become a powerful member of the Senate's inner circle, respected on both sides of the aisle, and Giuliani was transformed into "America's Mayor" for his calm and steady role in leading the city on 9/11.

The Rematch: Who's Ahead

Of course, it's early in the race and both candidates face pressure from strong competitors in their parties, but if it comes down to these old antagonists, who would win the rematch? While Giuliani often claims that he's the only Republican who can beat Clinton, they're both in a statistical dead heat, according to a recent poll.

As for the money game, Clinton has raised more than $90 million with $50 million in cash at hand, besting Giuliani's $47 million with $16.6 million in cash at hand. And she seems to have an advantage in a comparison between the two candidates' campaign contributors from both races.

Clinton's 2000 fundraisers are more loyal to their candidate, with roughly 19 percent of them writing checks for her presidential campaign, compared with 11 percent of Giuliani's 2000 fundraisers, according to an ABC News analysis of the numbers. (Only included are campaign contributions made before May 19, 2000, when Giuliani dropped out of the race due to his illness.)

And she has done a better job of converting her adversary's former fundraisers, including some notable personalities, by more than three to one.

At least 54 contributors to Giuliani's 2000 campaign, including Philadelphia Eagles owner Jeffrey Lurie, fashion designer Nicole Miller, financier Howard Gittis, General Electric vice chairman Bob Wright, and JPMorganChase executive Heidi Miller, have contributed to Clinton's presidential campaign.

And at least 14 contributors to Clinton's 2000 campaign, including fashion designer Mario Buatta, grocery store magnate and potential mayoral candidate John Catsimatidis, Paramount chairman Brad Grey, and cosmetics queen Evelyn Lauder, have contributed to Giuliani's presidential campaign.

Of course, the presidency is on a completely different level from the Senate and voters look for different qualities, including more leadership and management skills and less diplomacy.

In addition, New York is largely a Democratic state, and many of the candidates' 2000 fundraisers lived in the state, so they would be expected to support Clinton.

As is common practice with businessmen and lawyers, several fundraisers indicated that their 2000 contributions were intended to curry favor with the candidate, and not necessarily because they supported him or her.

Arzt, who donated $1,000 to Giuliani in 2000, and wrote a check for the same amount to Clinton this past September, says that he's always supported Clinton but he contributed to Giuliani, because "he was the sitting mayor, and no one pressures you to give, but you're trying to be good to the man in office."

Similarly, Buatta says he's written checks for candidates supported by his clients. Although he says Giuliani — to whom he contributed $1,000 in August 2007 — would make a good president, "I have no idea of whether I'm going to vote for him."

Many of these switch-hitters are making strategic decisions based on who they think is likely to win, says Muzzio. "There are many reasons for people to give to opposing candidates. They're making an investment, and they're more likely to make an investment with the person they believe is more likely to prevail."