The claim that Islam and liberalism are incompatible remains widespread. As a recent case in point, many cite the deterioration of Turkey’s democracy under President Recep Tayyip Erdogan and the Islamist-rooted Justice and Development Party (AKP). To explain what happened, secularist critics in Turkey and the West often blame a small group of liberals who allied with Islamists at pivotal moments, enabling AKP state capture. Liberal “treason,” it is argued, is inadmissible given the basic irreconcilability of Islamism and liberalism. Why then, this paper asks, have liberals in Turkey aligned with Islamists circa every 35 years for the past two centuries? After all, each of the five major Islamo-liberal alliances has collapsed. In their wake, liberals have been left, at best, by the wayside, and often imprisoned, exiled, or dead. Presuming that liberals are rational, how to explain the recurring alliance? And what does the answer suggest about the overall compatibility of Islam and democracy? To answer these questions, the paper proposes an original framework at the nexus of complexity theory and historical sociology with which to assess encounters between religious and liberal political projects in Turkey and beyond. Drawing on extensive primary data, including some 90 interviews conducted over a decade of field immersion, the paper examines a series of Islamo-liberal alliances that have demonstrably changed Turkey’s trajectory. Arguing that liberals engage Islamists to access power and advance pluralism in public life, the paper shows that when an alliance collapses, the cause is no clash of ideologies, but rather the contingent appropriation of liberal, Islamist, and other ideas by savvy politicians in response to domestic and international pressures. In other words, ideas alone are a necessary, but never a sufficient condition for coalitions to collapse. Rather, outcomes are determined by the causal interplay of ideas, agents, and structures at each critical juncture. By tracing when and why at some junctures Islamo-liberal synthesis succeeds, while at other junctures ethno-nationalist or ethno-religious nationalist platforms prevail, Pathways to Pluralism challenges the prevalent but misleading reading of Turkey and the Muslim world as torn by a perineal clash between secularists and Islamists.