The Nine Circles of Libertarian Hell
People who know about my political views, if asked to classify them, would probably describe me as broadly libertarian. I wouldn't really object to it, but would add the caveat that my libertarianism is pretty idiosyncratic and in the vein of Hayek and Schumpeter: Innovation (large and small) is the heart and soul of progressive human liberation, freedom is a necessary requisite for innovation to occur and for the benefits of innovation to disperse through the population, and this in turn enables greater freedom and innovation. So my vision of libertarian Hell will reflect my peculiar biases, but I think it's pretty good.
First Circle-The Virtuous Heathens: Those who care strongly about liberty in one particular sphere (e.g. freedom of speech, freedom of religious practice, the drug war, etc.) but don't care much about it in other spheres. These people are infuriating for their lack of general theory underlying their politics, but at least they've sorta got the right idea and can make themselves somewhat useful. This circle contains members of the NRA, ACLU & other such single-issue organizations, and is guarded by John Stuart Mill.
Second Circle-The Lustful: Those who fall madly in love with a dim vision they have of a more egalitarian society and then hastily rush off to elope with it, without giving much thought about just how much promise there really is in the relationship. These people's hearts are often in the right place but they show a frightening lack of concern for whether or not the policies they endorse are actually likely to accomplish the goals they desire. This circle is filled with innumerable bleeding-hearts and is guarded by Thomas Sowell.
Third Circle-The Gluttonous: Those who support illiberal policies simply out of percieved self-interest, and like to paint themselves as victims despite living at a level of material comfort that most previous generations would consider luxurious. Immigration & outsourcing restrictionists, farmers, labor unions, people who want to be insulated from the costs of their health care, etc. This circle is guarded by Benjamin Franklin.
Fourth Circle-The Greedy: Lobbyists who think their peculiar obsession should be the government's top priority. Corporations pleading for protectionism, finger-wagging nannies on a crusade to enforce "public virtue", and generally anyone else who wants everyone else to suffer for their sense of ideological privelege. This circle's most recent acquisition was the execrable Jack Valenti, and is guarded by Milton Friedman.
Fifth Circle-The Wrathful: People who are socialistic primarily out of an ugly resentment of the wealthy or anyone else they percieve as enjoying benefits they privately wish they could enjoy. Their instinct is not so much to see everyone doing well as to see those currently best-off doing much worse. This circle is guarded by Ayn Rand, which I think is a suitable punishment for both parties.
Sixth Circle-The Heretics: People who do seem to generally care about liberty but have an anomalous and largely sentimental attachment to illiberal policies in at least one sphere. They support freedom except the freedom to do drugs, or get an abortion, or freely migrate, or do anything they imagine undermines the war effort, etc. This circle is guarded by Ron Paul.
Seventh Cirle-The Violent: This circle is packed with tyrants of all kinds, politicians and bureaucrats-those who unquestionably do active violence to human freedom. (I would also add bad parents to this list.) They're enabled by the members of other circles, but it's these ones that actually do the trigger-pulling. This circle is guarded by Thomas Jefferson.
Eighth Circle-The Fraudulent: The Malebolge of public intellectuals-those who have a sphere of influence greater than most of us, and are negligent in their exercise of it by contributing to the darkness and confusion. This circle contains everyone from know-nothing idiots like like Lou Dobbs of CNN and Bob Herbert of the NYT, to people who are really smart enough to know better yet resolutely avoid any systematic examination of their moral premises, like Matthew Yglesias and Reihan Salam. (This latter group especially gives me the fucking creeps.) This circle is guarded by, who else, Friedrich Hayek.
Ninth Circle-The Traitors: The vast majority of lawyers and law professors, and also a significant number of economists, go here, in the deepest and darkest circle. Particularly the ones like Orin Kerr & Brad DeLong who are smart, reasonable, and may even have some pro-liberty sympathies, but when the time comes for action where it really counts they do a lot of showy handwringing before siding with illiberal policies. This is not so much due to a personality fault as due to simply having been warped by their professional training. This circle is guarded by David Friedman.