In any situation, the villain is the person who knows the most but cares the least.

So this is why Machiavelli shall always remain the figure that he is, especially among those who've never questioned why that pejorative connotation exists: He understood the dark. It's not for what he did, because he didn't really do anything; it's for what he understood about other people and for what he understood about himself. He didn't need to commit evil acts. He didn't have to be evil. That was just how his mind naturally worked, and that's what discomforts people. I realize such analysis sounds a little too easy. It seems like I'm suggesting that hardworking dumb people don't like slothful smart people, which ends up seeming like a #HUMBLEBRAG (nobody writes about the intellectual class without latently placing themselves in it, somehow). It also creates a problematic reflection: If a villain is the person who knows the most and cares the least, then a hero is the person who cares too much without knowing anything. It makes every hero seem like Forrest Gump. But it's not the intelligence that people dislike; it's the dispassionate application of that intelligence. It's the calculation. It's someone who views life as a game where the rules are poorly written and designed for abuse.

Everyone knows history is written by the winners, but that cliché misses a crucial detail: Over time, the winners are always the progressives. Conservatism can only win in the short term, because society cannot stop evolving (and social evolution inevitably dovetails with the agenda of those who see change as an abstract positive). It might take seventy years, but it always happens eventually. Serious historians are, almost without exception, self-styled progressives. Radical views--even the awful ones--improve with age.