In his Mediterranean and the Mediterranean World in the Age of Philip II, Braudel has described privateering, a paradigmatic form of Mediterranean conflict and exchange, as “…an ancient form of piracy native to the Mediterranean, with its own familiar customs, agreements and negotiation. While robbers and robbed were not actually accomplices before the event, like the popular figures of the Commedia dell’ Arte, they were well used to methods of bargaining and reaching terms…” The complicity formed between North African Muslim and Spanish Christian families hoping to ransom back their enslaved kin was expressed, in some cases, in unusual trust, an ad-hoc alliance that enabled the ransom of individual captives. Drawing on administrative, notorial and literary sources, this paper examines procedures that Muslim and Christian captives’ kin employed between 1580 and 1680 in order to liberate their dear ones from captivity in the Habsburg Empire and the Ottoman Maghrib. Many Maghribi wives and fathers bought Christian captives only in order to exchange them with their enslaved husband and sons. The execution of such exchanges required tight cooperation between families on both sides of the Mediterranean who negotiated their cases against Ottoman and Habsburg royal and religious bureaucracies. By examining these temporary coalitions, the paper explores the hitherto little studied ransom attempts performed by North Africans, and points out how the violent practice of capturing people in the sea lead to unexpected alliances between Christians and Muslims. Finally, it argues that rather than studying captivity and ransom of Muslim and Christian as separate phenomena, we should think of them as forming parts of a single Mediterranean system.