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When the 13 colonies in North America, the slave colony of Saint-Domingue, and the colonial territories of the Portuguese and Spanish Americas all rose against their imperial rulers, a new postcolonial order seemingly emerged in the Western Hemisphere. The reality of this situation forced political theorists and practitioners of the early 19th century to rethink the way in which they envisioned the nature and dynamics of international order. But a careful analysis of this shift reveals that it was not the radical break with prior notions of sovereignty and territoriality, often described in the literature. This was not the emergence of a new postimperial system of independent, nationally anchored states. Rather, it reflected a creative rethinking of existing notions of divided sovereignty and composite polities, rife with political experiments – from the formation of a new multi-centered empire in North America to the quasi-states and federations of Latin America. This moment of political experimentation and postcolonial order-making presented a distinctly new world repertoire of empire and state-building, parts of which were at least as violent and authoritarian as those of the old world empires it had replaced. The most radical ideas of freedom and liberty, championed by the black republic of Haiti, remained marginalized and sidelined by more conservative powers on both sides of the Atlantic.