On p. 96-7 of CIS, Rorty comes very close to spelling out an explicitly Pyrrhonist position: "The goal of ironist theory is to understand the metaphysical urge, the urge to theorize, so well that one becomes entirely free of it. Ironist theory is thus a ladder which is to be thrown away as soon as one has figured out what it was that drove one's predecessors to theorize." Remarkably, given the use of that familiar image, the accompanying footnote cites neither the ancient Skeptics nor even the early Wittgenstein (TLP 6.54), but instead the later Heidegger's "motto of ironist theorizing": "A regard to metaphysics still prevails even in the intention to overcome metaphysics. Therefore our task is to cease all overcoming, and leave metaphysics to itself" (Time and Being, 1962).
I don't know about Heidegger, but in Rorty the thought seems to be this. Traditional metaphysics is a mug's game; but if philosophers proceed in the usual fashion to try to show this once and for all, all we'll get is a philosophical theory, or doctrine, to that effect. But philosophical theorizing just is "metaphysics" in the controversial sense – that is, it succumbs to the same questionable urge (to escape finitude, or whatever). Instead of the traditional doctrines, then, we must target the urge which made them, or even their negations, seem necessary. If "overcoming" requires refutation, and refutation indulges the suspect urge, then we must abandon "overcoming" as well. We might not be happy about having to "leave metaphysics to itself," where anyone can still trip over it if they're not careful, but it can't be helped. We'll just have to develop other ways to help each other avoid that pitfall. Rorty's conception of pragmatism as "anti-authoritarianism," for example, exhorts us to spurn the siren song of metaphysical transcendence, with its chimerical promise of ideal grounding for our beliefs and values, in favor of more homespun methods of coping with our problems.
In chapter 5 ("Self-creation and affiliation: Proust, Nietzsche, and Heidegger"), Rorty explains why literature of a certain kind is better than philosophy for doing what needs to be done:
So the lesson I draw from Proust's example is that novels are a safer medium than theory for expressing one's recognition of the relativity and contingency of authority figures. For novels are usually about people – things which are, unlike general ideas and final vocabularies, quite evidently time-bound, embedded in a web of contingencies. [...] By contrast, books which are about ideas, even when written by historicists like Hegel and Nietzsche, look like descriptions of eternal relations between eternal objects, rather than genealogical accounts of the filiation of final vocabularies, showing how these vocabularites were engendered by haphazard matings, by who happened to bump into whom. [107-8]I'll get back to raking Rorty over the coals some other time, but let me get to my point here. To that last quotation is appended its own footnote, which reads: "There are, of course, novels like Thomas Mann's Doktor Faustus in which the characters are simply dressed-up generalities. The novel form cannot by itself insure a perception of contingency. It only makes it a bit harder to avoid this perception."
I like Mann a lot, but that's definitely a fair criticism (q.v. The Magic Mountain, or anything else for that matter). However, the impetus for this post is that I'm just now (very slowly) reading Doctor Faustus, and on p. 45 our narrator Dr. Zeitblom is telling us about the early years of his friend Leverkühn, the subject of the book:
In those years school life is life itself, it stands for all that life is, school interests bound the horizon that every life needs in order to develop values, through which, however relative they are, the character and the capacities are sustained. They can, however, do that, humanly speaking, only if the relativeness remains unrecognized. Belief in absolute values, illusory as it always is, seems to me a condition of life. But my friend's gifts [i.e., Leverkühn's] measured themselves against values the relative character of which seemed to lie open to him, without any visible possibility of any other relation which would have detracted from them as values. Bad pupils there are in plenty. But Adrian presented the singular phenomenon of a bad pupil as the head of the class. I say that it distressed me, but how impressive, how fascinating, I found it too! How it strengthened my devotion to him, mingling with it – can one understand why? – something like pain, like hopelessness! [Lowe-Porter translation, altered slightly]So described, the young composer sounds quite a bit like Rorty's "ironist," and indeed, the next paragraph discusses "one exception [i.e., mathematics] to [Leverkühn's] uniform ironic contempt." Here, though, the skepticism is explicit. Belief in absolute values, however necessary "as a condition of life," is always illusory. The only alternative to "absolute" is "relative," and regarding some value as (merely) "relative" is equivalent to rejecting any claims it may have to validity. Where Leverkühn differs from Zeitblom is that the former did not let the recognized illusoriness of absolute value stop him from acting as if he accepted it. He even excelled at what others took seriously, while he himself saw it as merely a game – one he was good at, but a game nonetheless.
No doubt Rorty takes his own position to differ, not simply from Zeitblom's, but also from that of Leverkühn. (He might, for example, have mentioned this passage as anticipating his own views, rather than simply knocking the book for not being sufficiently Proustian.) As I read him, I think Rorty would say that in allowing a norm or value to structure one's actions – to be seen as "playing the game" at all – is, in that context, to accept it as fully as it makes sense to do so. To demand a further "metaphysical" commitment to its truth (pardon me, Truth) is to fall into unintelligibility, or at least disutility. That's why recognizing "contingency" isn't the same as skepticism or nihilism.
Now, this is indeed a more attractive thing to say. It's just that I don't think Rorty can do so consistently. For example, Rorty tells us repeatedly that his pragmatism points us past the "stale dichotomy of realism and anti-realism"; but he just as consistently endorses anti-realist doctrine when it suits him, as in the continuation of the very definition of "ironism" with which I began. Ironists, he says, are that way because they are "sufficiently historicist and nominalist to have abandoned the idea that those central beliefs and desires refer back to something beyond the reach of time and chance." Naturally going "beyond realism" will involve rejecting realist doctrines like this one. Still, when overt appeals to anti-realism are qualified, in the definition of the central concept of one's view, only by words like "sufficiently," it's hard to see how that itself is sufficient for us to avoid the one as well as the other.