This paper deals with Edgar Wind’s texts on symbols and cultural memory from the early 1930s. It emphasizes in particular the connection these texts establish between Warburg’s ideas and the pragmatist philosophy to which Wind was exposed during his first stay in the United States. I will argue that Wind’s interpretation of the polarity of symbols takes up a quintessential pragmatist focus on habit as the mechanism that lets us understand how expressive gestures develop out of practical actions. I will then show that Wind used the idea of a mnemonic power of symbols to fine-tune the pragmatist conception of thought and action as a permanent oscillation between doubt and belief.