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This chapter examines the transnational organizing and social networking that connected various freedom struggles in the United States and Caribbean in the 1860s and 1870s. Beginning with the effects of the hurricane that hit the Turks and Caicos Islands in September 1866, it follows Henry C. C. Astwood’s migratory trajectory from the Turks Islands to Puerto Plata to Samaná and finally to New Orleans. This chapter demonstrates how people of color in each locale united and adapted their strategies in their struggles for liberty. It especially highlights Black Protestant churches in the Dominican Republic and the US South as centers of communal political organizing. By involving himself in religious and political activities in each place, Astwood built his reputation as a moral leader and achieved upward mobility. His participation in the fight for Black rights in New Orleans ultimately landed him the position of US consul to Santo Domingo.

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