Guiliani
As my libertarian and libertarian leaning friends have been bringing him up lately, here is a negative portrait of Rudy Guiliani.
And to expand on my bar rant of last night, he would make a great mayor (New Orleans needs one right now), and would probably make a great president if it were the year 1880. However, in our modern age presidents have far too much discretionary power, and pro-choice, thrice married, adulterous Catholics are far too good at living with contradictions to be trusted to keep their promises.