Rudy!

Looking forward to 2008, I can say that I don't envy the Republicans one bit. I see three fairly strong Democratic leading Candidates (Obama, Clinton, Edwards) with a strong pool of possible breakthrough or vice presidential candidates (Richardson, Clark, Warner, Sebellius.) The three leading Republicans (Giuliani, McCain, Romney)all have serious personal issues and political issues that are likely to be problematic in the primary, general election, or both. I find their second tier of "true conservative" candidates to be a mix of terrifying (Brownback, Newt Gingrich) and odd, (Huckabee) but not very threatening in terms of the general election.

But about Giuliani.
The bad: The man is a complete and total asshole, personally and politically. He has no ability to build personal or political coalitions, because he's not a nice person, and he's more interested in carrying out personal vendettas than getting things done. He has had a truly messy and public divorce, which he came out of looking like a jerk. He tried to use 9/11 to change the city charter and extend his term as mayor. His one moment in the national spotlight since 9/11 involved getting the incredibly corrupt Bernard Kerik (his former police chief) nominated for Homeland Security Secretary for about two minutes, until he withdrew amidst several different simultaneous corruption scandals. His campaign managed to lose their campaign plan, so the entire thing is now available online.

The good: He's a competent manager, sort of. He was mayor of NYC when 9/11 happened.

He has major problems in the primary. Giuliani's current position is that he hates abortion, but he's pro-choice, but "mumble mumble states rights, strict constructionists mumble mumble." Color me unimpressed. The Republican base is not gonna go with that unless they have to. He's also catholic. Anti-catholic racism is something you don't hear about that much, but only three Catholics have ever been nominated to be presidential candidates, and they were all Democrats. Both Al Smith and John F. Kennedy had to defend themselves against accusations that they'd be taking orders from the Church, and Kerry (ironically) had to defend himself against accusations that he wasn't taking orders from the Church because he was pro-choice. Maybe the Republican primary voters are ready to elect a Catholic, but I don't think it should be assumed.

The real reason for Giuliani's pre-9/11 popularity in NYC, as far as I can tell, (I'll admit to not remembering his terms all that well) is that he made middle-class white people feel safe, partly through OK police policies, and partly through playing up racist tensions, locking up homeless people, and generally being an SOB. Playing up racial tensions against blacks has certainly a successful electoral strategy for Republicans in the general election before. It has a name; the "Southern Strategy." The problem with Rudy Giuliani being the heir to the Southern Strategy is that he's an Italian, Catholic, New Yorker who is on the record as pro-gay and pro-choice. If there is anything that would give Virginia and North Carolina to the Dems, it would be a Giuliani/Edwards race.

Occasionally you hear people say that Giuliani could win the general election because he could take New York State. I can't imagine he could run far enough to the left to make NY competitive, but even if he did, New Yorkers (Upstate and down) would almost certainly still vote for Clinton over him.

Finally, there is 9/11. He will have to wrap himself in September 11th and hawkishness if he hopes to have a damn chance of winning anything ever again. He's certainly proved to be shamelessly adept at doing this, but it just won't last. Republicans used 9/11 successfully in 2002 and 2004, but the war vastly overshadowed it as an issue in 2006. And in case you didn't notice, people aren't holding the Democrats responsible for that disaster. There isn't really any way for Giuliani to position himself as an anti-war candidate without giving up the 9/11 talk, so he's basically stuck embracing what will be an even more hugely unpopular war in 2008.

Obviously, there are many many things that could totally alter the landscape before the primaries happen, but looking at how things stand now, I see his chances of making it through both the primary and general election as close to zero.