Transplanted from The Pragmatic Critique of Analytic Philosophy -- it fits a bit better here:
Unlike JerboaKolinowski I'd lump Wittgenstein roughly in with Rorty. I'd like to consider why pragmatism looks like a failure to me. It seems that presentations of pragmatic, conventionalist or relativistic notions of truth are necessarily bound to a 'book' or 'long' form of discussion to be really plausible. Who can deny that Wittgenstein's less analytic writings (which I do admire) have their force magnified many times by their presentation in meandering volumes? I say 'long' in comparison to the unit of analytic philosophy as most effectively practised, which is the short paper: the concise presentation of a logical or evidential point.
Heavy analysis does often become repetitive and dry in the course of a cohesive book. But a 'pragmatic', ironic or reactionary doctrine is better presented in this format because drawn-out criticisms of the 'analysts' are necessary, and because musings rather than succinctly summarisable deductions are required. After all, the pragmatist must steer clear of substantive theorizing if their thesis that philosophy is 'content-free' is to hold. Also, pragmatism respects the plurality of human viewpoints and traditions in a way that is alien to the analytic style. It introduces complexities and in doing so seeks a better understanding of practice -- even if this understanding should be of a form that undermines our belief in the significance of philosophy.
And this illustrates the reason why pragmatism defeats itself. It is so much more expedient to use the pre-ironic framework to get things done than it is to try to grasp and use the ironic one, that the ironic framework should call itself a failure.