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From Slate

The factor which hasn't been much discussed. Rudy would almost certainly have lost to Hillary Clinton even if he were in good health and happily married.

The reason is that New York is now firmly in the Democratic column in presidential elections.
In 1992, Bill Clinton beat George Bush in New York by 16 percentage points, making it his second-best state after Arkansas. In 1996, Clinton clobbered Bob Dole in the state by 28 points, a margin of more than 1.5 million votes. Only in Massachusetts and Rhode Island did Clinton win by a wider margin that year. Based on this precedent--and on his 20-point lead in the most recent poll--Al Gore can be expected to sweep New York by another double-digit margin in November. And because of these numbers, George W. Bush can be expected to not contest New York in any serious way. Instead, he will focus his energies and resources on states where he has a realistic chance of winning.

Even in presidential off years, New York tilts heavily to the Democratic side.
It now has two Democratic senators, Daniel Patrick Moynihan and Charles Schumer, while 18 out of its 31 representatives in Congress are Democrats. The best-known state officials other than the governor are Attorney General Eliot Spitzer and Comptroller Carl McCall, both Democrats. The sole prominent Republican who has been elected statewide lately is Gov. George Pataki. But it's worth noting that Pataki scored his upset victory over Mario Cuomo in 1994, a presidential off year. Pataki was re-elected in 1998 (by an admittedly huge margin) in another presidential off year. The only significant statewide victory by a Republican in a recent presidential election year was in 1992, when the well-funded incumbent Sen. Alfonse D'Amato beat an inept Democratic challenger, Robert Abrams, by the narrowest of margins--80,000 votes.

So, the bet's in favor of Hillary against Rep. Rick Lazio who is taking up Rudy's place in the New York Senate race.