One of the most salient features of the medieval Mediterranean is that it was a zone of intense interaction and long-term cohabitation of members of various ethno-religious communities whose relations are usually conceived of as fundamentally adversarial. Yet Christians, Muslims, and Jews lived amongst each other in both the Christian- and Muslim-ruled Mediterranean, even during the era of the crusades. Typically, such relationships have been presented as either fundamentally hostile, or cordial, and as related to the “tolerance” that host cultures were inclined to demonstrate as a consequence of their own religious orientation. This paper takes a different, phenomenological approach by focusing on a specific manifestation of this interaction: the emergence of out-group political elites in confessionally defined societies. Through the medium of three case studies—a powerful Jew in Islamic Spain, a powerful Muslim in Norman Sicily and a powerful Coptic Christian in Fatimid Egypt—I demonstrate that the status of minority elites was related to concrete political circumstances grounded in the particular environment of the region, and that, despite cultural differences that might have distinguished them, these societies developed near-identical strategies for engaging with minority elites. The language of religious polemic, exclusion, and marginalization was present, but it tended to serve as a post factum rationalization for repression rather than its cause, and tended to be deployed decisively only in certain circumstances. This provides new insights not only into Muslim-Christian-Jewish relations, but the fundamental nature of Mediterranean history and society.