In this paper, I examine the transmission of some ideas of the pragmatist tradition to Wittgenstein, in his ‘middle period,’ through the intermediary of F. P. Ramsey, with whom he had numerous fruitful discussions at Cambridge in 1929. I argue more specifically that one must first come to terms with Ramsey’s own views in 1929, and explain how they differ from views expressed in earlier papers from 1925-27, so a large part of this paper is devoted to this task. One is then in a better position to understand the impact of Ramsey’s astute critique of Wittgenstein’s Tractatus Logico-Philosophicus in conjunction with his pragmatism, and explain how it may have set into motion the ‘later’ Wittgenstein. I then argue that Ramsey introduced his notion of ‘variable hypothetical’ as a rule, not a proposition, on pragmatist grounds and that Wittgenstein picked this up in 1929, along with a more ‘dynamic’ view of meaning than the ‘static’ view of the Tractatus, and that this explains in part Wittgenstein’s turn to his ‘later philosophy.’