While surfing in the summer of 2008, one particular surfer was blatantly breaking the rules of right-of-way, and I found myself thinking "Jeez, he's an asshole." That was not a new thought, but this time it occurred to me that it had what philosophers call "cognitive content." I wasn't just venting disapproval, but classifying the guy as a certain kind of person, in a way that could be either true or false of him. In contrast with the other surfers in the line up, who weren't properly classified as assholes, he was. After considering how similar he was to a couple of other people I've known, I put my philosophical training to use, with the help of some friends, and came up with this definition: the asshole is a person who systematically allows himself special advantages in cooperative life out of an entrenched sense of entitlement that immunizes him against the complaints of other people.
I decided that the idea of a "sense of entitlement" should be left open-ended. The term "asshole" isn't terribly precise, and (as Aristotle taught) that imprecision should be respected. This also meant that assholes could come in different styles: they can feel mistakenly entitled in very different ways. The "asshole boss" is emboldened by the entitlements that come with his role in the workplace, while the "smug asshole" feels superior in his personal qualities. This way, the theory leaves us with a game of pin the tail on the donkey--a game, for the sporting, that turns out to be lots of fun. We get to decide who is or is not an asshole, and whether we think he is wrong about what he believes he is entitled to.
It should be said that the game does pose real risks of unfairness to real people. Public figures arguably do assume those risks when they conspicuously misbehave. Even so, I try to stick to clear-cut cases and telling details. Otherwise, I stand ready to apologize profusely if I've misclassified someone. Here, for what it is worth, are some of my own (tentative) opinions about some familiar figures.
Aaron James is the author of Assholes: A Theory.