Andrew Ferguson of the Weekly Standard takes a good, hard look at Giuliani (the title is the link--I'm gonna mention that a lot for a while--to get people used to it), and sees things that make him think that Rudy as the GOP Nominee will be bad news for conservatives:
Giuliani cites his triumph in New York in the 1990s--along with the sensitive and courageous performance of his duties during the chaos of September 11, 2001--as his chief qualification for the presidency. Yet voters will be entitled to wonder whether the triumph is transplantable to a different time, on a different scale, in a much larger, two-party political culture that is not nearly so irrational and self-destructive as New York City's. The personal temperament and "management style" he displayed as mayor, not unusual for New York, are hard to imagine in the Oval Office. "People didn't elect me to be a conciliator," he told Time magazine at the end of his second term. "If they just wanted a nice guy they would have stayed with [David Dinkins, his feckless predecessor]. They wanted someone who was going to change this place. How do you expect me to change it if I don't fight with somebody? You don't change ingrained human behavior without confrontation, turmoil, anger."
How would such a rough-edged approach appeal to those moderation-loving centrists who, Giuliani supporters claim, the candidate will attract to the Republican party in uncountable numbers? Even in New York his public personality wore thin. Three months before the end of his term Giuliani's poll ratings had fallen to George W. Bush-like levels--only one in three New Yorkers approved of his performance. The dip followed an excruciating personal difficulty that Giuliani himself thrust into public view. In early 2000, at a press conference on an unrelated matter, Giuliani suddenly announced to the assembled reporters that he was divorcing his second wife. The second wife, for her part, held a press conference of her own a few hours later to announce that the mayor's announcement was the first she'd heard of any divorce. She couldn't have been terribly surprised, though. By this time, the mayor had abandoned his official residence, moved in with friends, and taken to appearing at public functions with another woman, Judi Nathan, whom he would eventually marry three years later. The second wife and their two children were left to themselves in the mayor's mansion. The kids were 14 and 10 at the time. It's not necessary to imagine what all those moderation-loving centrists will make of this episode; just imagine what a Democratic ad-maker will make of it.
That right there tells me that Giuliani, once that story gets wider exposure, will become highly unpalatable to many people. Ferguson, however, has more rounds to fire:
Simply put, Giuliani is the darling of the Nelson Rockefeller wing of the GOP simply because he's not a conservative. And if he is nominated, the Democrats will do a dance for joy.
It was an interesting platform that Giuliani offered his audience [in San Francisco]--and that he intends to set before voters as the campaign progresses. He spoke of reforming Medicaid spending by giving vouchers to the poor. He suggested rebuilding the No Child Left Behind school reform by giving vouchers for parents to choose schools among private and public options. He endorsed a government-sponsored, NASA-like program to develop alternative sources of energy. Americans, he said, should have the choice of accepting the Social Security system or opening a private account instead. At the same time he suggested strengthening electronic provisions of the Patriot Act, and supporting "tough, intense interrogation" techniques against terrorists. Add the endorsement of gay rights and abortion rights, and it's an unusual stew.
Giuliani is routinely described, in the pundit's shorthand, as a moderate, and Fred Siegel, the Cooper Union scholar, coined the term "immoderate centrism" to describe Giuliani's politics. But watching the mayor lay out his views you begin to see that Siegel's term is only half correct. Giuliani's not a centrist at all. He's that rare politician who's most comfortable staking out positions at the further points of the ideological spectrum, swinging from one end to the other depending on the issue at hand, and passing over the middle altogether. Rather than appeal to the "center," as his supporters claim, it is just as likely that Giuliani's social liberalism will offend conservatives and his fiscal conservatism will offend liberals.