[Wittgenstein] never adopted the phenomenalist thesis that physical theories can be translated into the set of propositions describing the observable states of affairs that would confirm them…he declared the confirmation of a hypothesis is never completed. In the same set of remarks he characterized a hypothesis as ‘a law for forming propositions’ or alternatively as ‘a law for forming expectations.’ I think he can most fairly be said to have treated the experiences which would fulfil these expectations as constituting the ‘cash-value’ of the hypothesis. ‘Cash-value’ is a term employed for this purpose by William James, a philosopher whom I believe Wittgenstein respected. At any rate, his dicta of this period fit easily into the pragmatist tradition….The pragmatic tenor of Wittgenstein’s thinking at this period is again in evidence in the early part of The Blue Book. We are advised at the outset to substitute for the question ‘What is the meaning of the word?’, the question ‘What is an explanation of the meaning of the word?’ or ‘What does the explanation of a word look like?’ One immediate benefit of this approach is that it diminishes the temptation to think of meanings as a special category of objects, or that of being satisfied with any general set of answers conforming to the pattern of the assertion that predicates stand for properties. Wittgenstein sees that the fundamental problem is that of explaining how a series of noises or written marks acquires what he calls a life. His own general answer is that ‘if we had to name anything as the life of the sign, we should have to say that it was its use.’ [pp. 41-43; link added]
The relationship between Wittgenstein’s writings and those of the pragmatists are now quite well established. (A quick google of ‘Wittgenstein pragmatist’ or ‘Wittgenstein pragmatism’ shows this quite easily.) So is his supposed affinity with Williams James (as noted by Ayer above.) For my part, long before I had read any formal or theoretical analyses of Wittgenstein’s relationship to pragmatism it had seemed to me that someone committed to a use theory of meaning would find the pragmatist criterion of meaning and truth quite amenable. When I began drawing up my syllabus for my graduate seminar on pragmatism a few years ago at the CUNY Graduate Center, I pushed a bit further in the direction of this supposed connection and was immediately gratified to find the extensive literature above; I went on to draw on sections of Russell Goodman‘s Wittgenstein and William James.
My students’ reactions then, to finding Wittgenstein on their pragmatism syllabus is not an uncommon response to the claim that Wittgenstein can be considered a pragmatist of sorts; in large part, this is a reaction to writing styles. The classical pragmatists–Dewey, Pierce, and James–are all generally acknowledged to be clear writers (even if Dewey is regarded correctly as excessively verbose.) Wittgenstein, of course, is famously cryptic on all too many occasions; Ayer notes, as have many others, that he was better at providing suggestive and provocative examples than he was at providing trains of rigorous arguments. (A similar reaction of surprise is expressed by some when told that Nietzsche and the pragmatists are often in sympathy with each other.) The discovery of these resonances and others like them further help establish the claim that the pragmatists are not a sui generis phenomenon but rather, represent a recurring strain and orientation in philosophy.