In recent years I've become more and more convinced that the soundness of particular arguments are more important than their rhetorical value. Unfortunately, in a world of soundbytes, memes, and an ever-shrinking fifteen minutes of fame, brevity is an increasingly important aspect in the world of swayed opinions. Arguments that essentially boil down to one-liners can be particularly powerful, much like the jokes of stand-up comedians. They can put forth what appears to be a casually obvious absurdity to prove a specific point. Of course, the problem is that when all its underlying assumptions are unbound, the line of thought often quickly falls apart. The truth is that, while the illustration of such apparent absurdities may take the audience captive, they are often imaginatively fragmented and unrealistic. And by dosing each other with such arguments, even if they offer us short term victories, we are simply teaching people to accept bad arguments in the long run.
What got my wheels turning on this was the Lind piece on Salon from a few days ago - "The Question that Libertarians Just Can't Answer". A question which, by the way, was not only irrelevant in many ways (to the greater argument for libertarianism), but was actually easily answerable without too much reflection. The burning question: "If libertarianism is so great, why hasn't any country anywhere in the world ever tried it?" Now, apparently, this is being seen as a quite damning question by most non-libertarians. The question was certainly rhetorically effective in that sense. But I felt it to be more frustrating than anything - in that, at its base, it seemed somewhat ambiguous, and even nonsensical.
For instance, this question relies terribly on a term which covers a pretty wide spectrum of ideas. A libertarian could be a minarchist, a liberal, a socialist, a classical liberal, a paleo-conservative, an anarcho-capitalist, a voluntaryist, a free-market anarchist, and so on. Some may quibble that such variance lies only in degrees but anyone familiar with these groups knows that there are substantive differences between them. And, depending on which group you subscribe to, you could make some pretty remarkable arguments that your ideas (or at least substantial parts of them) are certainly being incorporated in most Western societies at this point (especially if you fall within the first few groups I mentioned). So even from the start, we see this lack of defining in our terms.
What kinds of presumptions lie in such a question? It seems to make the implicit claim that if libertarianism actually "works" (whatever sense of the word one wishes to employ) that at least some national governments would have adopted such policies. But some conceptions of libertarianism see national governments themselves as the antithesis of libertarian ideals. From that view, the question becomes something like, "Why doesn't oligopoly dissolve itself?" - to which they might all heartily answer, "Haha!" This was essentially the overture Tom Woods made to the question. And it's a powerful one.
Another possible implicit claim in the question is that arguments about institutions are purely utilitarian - ie, the correct one is the the one that "works". Now, I think there is at least somewhat of a false dichotomy when it comes to utilitarian vs. deontological concerns, but I digress. To the extent that the argument for libertarianism is a seemingly non-utilitarian one, the question, again, fails to make any semblance of sense. We can view libertarian ideals as not necessarily just a means to a particular end, but part of the ends themselves. In a more straight-forward example, we could ask, "If killing and stealing didn't work, then why do so many people kill and steal?" Well, that's certainly a question worth entertaining, but is it really an effective argument against, well, killing and stealing? I'd venture to say it's not.
And this only begins to scratch the surface of how truly problematic the question is. Another implied assumption seems to be that the present is optimal, for lack of a better term. We seem to be fed a question of, "Look - if this thing is so great, why don't we see it?". But that's a silly kind of question on its face - one that could have been asked about anything we currently cherish at some point prior to its advent. We could have, for instance, asked the same questions about democracy or the abolition of slavery at various points. That the world was entrenched in a certain paradigm at one point does not speak to other paradigms it could employ, or the justness of the current one. It takes a keenly myopic view of humanity's historical progression to lapse into such frivolities - particularly when one's mantle is "Progressive".
I don't point these things out in an effort to just bash the people I disagree with. Libertarians use the same kind of rhetorically short-hand arguments all the time. And I'm just as guilty as the next guy of doing it from time to time. But I think it's good to make a concerted effort not to, even if you believe it gives those who do engage in it an upper hand. If you really think the best arguments should prevail, and you also believe you have the best arguments, then you should really try to foster that kind of environment whenever you can.