Poet Ezra Pound wrote a letter on February 6, 1940, inviting philosopher George Santayana to join poet T. S. Eliot and himself in writing a book on the ideal university. Santayana declined the invitation, claiming to have no ideas on education. Participation would have been morally impossible, he wrote, because unlike Pound and Eliot, he was "cynically content to let people educate or neglect themselves as they may prefer." I propose to take seriously Pound's sense that Santayana has something to say about education. In this speculative, rather than historical, essay, I read Santayana with an eye to what "conceivably" could have appealed to Pound. I aim to suggest deeper connections between the two thinkers than have previously been noted, and to consider how their common concerns can benefit a reader concerned with pedagogy. (Contains 85 notes.)