There has been some dispute among libertarians, especially lately, as to whether our best prospects for winning people over to libertarianism come mostly from the left or the right. I myself came from the right, so I'm certainly not going to suggest that trying to persuade conservatives is futile. My suspicion, though, is that by this point, most of the low-hanging fruit on that side of the spectrum has already been picked; I think that most people who still consider themselves loyal Republicans after six years of Bush, the war, the domestic spending increases, etc. are probably not going to be readily converted at this point, even if they agree with us on a few issues like guns. Paleoconservatives and other conservative dissidents are a better prospect, but they don't appear to be very numerous compared to all the Bush fans on the right.
I don't hold out much hope for winning over moderates; they have generally fully absorbed the consensus "vital center" big government view of the political system and of American history, and usually approach seem to approach politics with no strong principles other than a general willingness to use state compulsion for some vaguely defined "public interest" or the latest trendy cause. These people are often the most statist- they have a tendency to support the bad parts of the left and the right in one giant potluck dinner of evil. That's what makes them so reasonable and non-ideological and pragmatic, after all.
I think the left may become a more fertile recruiting ground because, for the last few years, they've learned a hard lesson: sometimes your foes will be in control. Government abuses like Waco under the Clinton administration turned my old Republican self into a libertarian, by showing me how nasty the state can be; I'm hoping Bush will have a similar effect on some people on the left. My observation is that the human ability to learn from experience is not terribly high when applied to politics, but there's a chance.
How likely is it that a significant number of leftists can be won over? That's hard to answer, because the answer depends on precisely what the attitude of the majority of leftists is. I think there are some leftists who are reachable, and some who aren't. There are leftists who value liberty and prosperity for the people but pursue them in a mistaken way, and then there are leftists who are basically throne and altar reactionaries in modern drag- there's a different God on the altar and a different ass on the throne, but the basis of their philosophy remains a belief that the brutish masses need to be dominated by an elite (democratically legitimated or otherwise) for their own good.Most of the second group can be written off as a lost cause; the first group has potential. I'm less optimistic about our prospects than some, because I think the second group comprises a pretty big percentage of the whole (though I admit the possibility that their noisiness is out of proportion to their size), but I still think there's some potential there. Whether that potential can be successfully tapped will depend on adoption of the proper tactics of persuasion. I'll get into that next time.