Odd as it may seem, there are libertarians who are Giuliani enthusiasts--and some who even find "America's Mayor" "electrifying." David Boaz and David Weigel each provide some very good reasons to doubt that a Rudy presidency would be good for American liberty, among them his 1980s prosecutorial "reign of terror" against Wall Street, his unhinged approach to foreign policy, and an authoritarian streak that ought to disturb civil libertarians. But for a shorter indictment, it's hard to beat this anecdote from Newsweek's recent feature "Growing Up Giuliani", in which the ambitious, officious young Rudy sounds like a cross between Douglas C. Neidermeyer and Tracy Flick:
Giuliani managed a friend's campaign that year, hiring a U-Haul with a loudspeaker to cruise outside the school, but his highest office was hall monitor. He seemed to enjoy wearing a badge and disciplining students for minor infractions, such as talking during a fire drill. "He had a stern look," says Jack J. Rengstl, another former Loughlin student. In the yearbook, in the usual "Most likely to …" categories, he was voted "Class Politician."