Masud Khan was one of the most brilliant psychoanalysts of the Twentieth Century. He was Winnicott’s “principal disciple,” and analysand. He was also one of the most troubled analysts, dying in madness, despair, and alone. How could such a talented and celebrated psychoanalyst fall so dramatically and publicly? In response to this question, his analysis with Donald Winnicott remains a focus of theorizing and controversy. This paper argues that it was Khan’s radical otherness—his identification as a “feudalist,” standing outside of a Western, democratic worldview—that served as a significant reason for the failure of his analysis. In defying the confines of his analytic community’s social unconscious, Khan’s descent allows us to question the ways in which we think about difference and otherness today.