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Many classic studies of leadership focus on strong leadership in the singular. This essay focuses on effective leaderships in the plural. Some of the greatest failures of democratic transitions (Egypt, Syria, Libya) have multiple but highly conflictual leaderships. However, a key lesson in democratization theory is that successful democratic transitions often involve the formation of a powerful coalition, within the opposition, of one-time enemies. This was accomplished in Chile, Spain, and Indonesia. In greater detail, this essay examines Tunisia, the sole reasonably successful democratic transition of the Arab Spring. In all four cases, religious tensions had once figured prominently, yet were safely transcended by the actions of multiple leaders via mutual ideological and religious accommodations, negotiated socioeconomic pacts, and unprecedented political cooperation. A multiplicity of cooperating leaders, rather than a single “strong leader,” produced effective democratic leadership in Tunisia, Indonesia, Spain, and Chile.