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This chapter follows Simón Bolívar, one of the most important figures of the wars of independence in Spanish America, as he sought to revitalize the struggle for Spanish America’s independence in the Caribbean islands of Jamaica and Haiti. It advances four arguments. First, Alexandre Pétion’s proinsurgent diplomacy and Jamaican authorities’ adherence to British neutrality allowed Haiti to emerge as an international revolutionary center actively spreading revolution throughout the Greater Caribbean. Second, the gradual success of British military campaigns against Napoleon and Caribbean-wide fears of the spread of Haitian revolutionary ideals accounted for Jamaican authorities’ unwillingness to openly support Spanish American insurgents. Third, guaranteeing British neutrality policy and attempting to hold Pétion true to his promise of neutrality required policing and diplomatic pressure from Spanish officials in New Granada, Venezuela, and the Spanish Caribbean islands. Finally, a combination of news about developments in Europe, personal fears of the Haitian Revolution, and Enlightenment ideas about race and civilization informed Bolívar’s action plan and expectations for support during his Caribbean journey. The chapter is organized into four sections. The first presents the Atlantic and Caribbean settings for the international campaigns of Bolívar and many other Venezuelan and Neogranadan émigrés. The second and third sections tackle Simón Bolívar’s activities in Jamaica and Haiti, explaining for both cases what Bolívar expected to get and what he actually achieved on both islands. The final section explains the political and ideological foundations of Bolívar’s expectations.

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