I'm not sure he belongs on a list of philosophers, but since he's been put here I'll make the best of it.
Probably the political and social theoretician who is most misunderstood by people who have never read his work. I see from some of the other comments left here that this is, unsurprisingly, the case on RIA as well.
Machiavelli understood clearly that without power, nothing can be achieved, either good or ill. He counselled the acquisition and exercise of power in a manner indicating that he understood power in a thoroughly practical way.
He does not, as some attest, counsel tyranny for its own sake. His work has to be read in the context of the time, but having said that, many of his theories are applicable today.