Someone on Yahoo!Answers recently asked with which US political party would Niccolo Machiavelli associate himself if he were alive today.
It actually isn't a bad question. I offered this answer.
Machiavelli was an Italian nationalist. He was enthusiastic about an unscrupulous Prince because he believed only such a Prince could free Italy from the clutches of foreign powers. I suspect he would be a Trump supporter if he were a US nationalist with a similar orientation today. So, at least for the purposes of supporting Trump (not more widely) he would affiliate with the Republican Party.