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Jamaica, Haiti, Venezuela, and New Granada: 1815–1819

Bolívar arrived in Kingston, Jamaica, on 14 May 1815 and, as in his earlier exile on Curaçao, ruminated on the fall of the Venezuelan and New Granadan republics. He wrote extensively, requesting assistance from Britain and corresponding with merchants based in the Caribbean. This culminated in September 1815 with the Jamaica Letter, in which Bolívar again laid out his ideology and vision of the future of the Americas. On 9 December, the Venezuelan pirate Renato Beluche brought Bolívar news from New Granada and asked him to join the Republican community in exile in Haiti. Bolívar tentatively accepted and escaped assassination that night when his manservant mistakenly killed his paymaster as part of a Spanish plot. He left Jamaica eight days later, arrived in Les Cayes on 24 December, and on 2 January 1816 was introduced to Alexandre Pétion, President of the Republic of Haiti by a mutual friend. Bolívar and Pétion impressed and befriended each other and, after Bolívar pledged to free every slave in the areas he occupied, Pétion gave him money and military supplies.

Returning to Les Cayes, Bolívar held a conference with the Republican leaders in Haiti and was made supreme leader with Mariño as his chief of staff. The Republicans departed Les Cayes for Venezuela on 31 March 1816 and followed the Antilles eastward. After a delay to allow a lover of Bolívar's to join the fleet, it arrived on 2 May at Margarita Island, controlled by Republican commander Juan Bautista Arismendi. Bolívar next moved to the mainland, where he declared the emancipation of all slaves and annulled of the Decree of War to the Death. He seized Carúpano on 31 May and sent Mariño and Piar into Guayana to build their own army, then took and held Ocumare de la Costa from 6 to 14 July, when it was recaptured by the Royalists. Bolívar fled by sea to Güiria where, on 22 August, he was deposed by Mariño and Venezuelan Republican José Francisco Bermúdez.

Bolívar returned to Haiti by early September, where Pétion again agreed to assist him. In his absence, the Republican leaders scattered across Venezuela, concentrating in the Llanos, and became disunited warlords. Unwilling to recognize Mariño's leadership, Arismendi wrote to Bolívar and dispatched New Granadan Republican Francisco Antonio Zea to convince him to return. Bolívar and Zea set sail for Venezuela on 21 December with Luis Brión, a Dutch merchant, and arrived ten days later at Barcelona. There, Bolívar announced his return and called for a congress for a new, third republic. He wrote to the Republican leaders, especially José Antonio Páez, who controlled most of the western Llanos, to unite under his leadership. On 8 January 1817, Bolívar marched towards Caracas but was defeated at the Battle of Clarines and pursued to Barcelona by a larger Royalist force. At Bolívar's request, Mariño arrived on 8 February with Bermúdez, who then reconciled with Bolívar, and forced a Royalist withdrawal.

Even with their combined forces, however, Bolívar, Mariño, and Bermúdez could not hold Barcelona. Instead, on 25 March 1817, Bolívar began moving south to join Piar in Guayana, Piar's power base, and establish his own economic and political base there. Bolívar met Piar on 4 April, promoted him to the rank of general of the army, and then joined a force of Piar's troops besieging the city of Angostura (now Ciudad Bolívar) on 2 May. Meanwhile, Mariño went east to reestablish his power base and on 8 May convened a congress of ten men, including Brión and Zea, that named Mariño as supreme commander of the Republican forces. This backfired and provoked the defection of 30 officers, including Rafael Urdaneta and Antonio José de Sucre, to Bolívar. On 30 June, Bolívar granted Piar leave of absence at his request, and then issued an arrest warrant on 23 July after Piar began fomenting rebellion, alleging that Bolívar had dismissed him because of his mulatto heritage. Piar was captured on 27 September as he fled to join Mariño and was brought to Angostura, where he was executed by firing squad on 16 October. Bolívar then sent Sucre to reconcile with Mariño, who pledged loyalty to Bolívar on 26 January 1818.

On 17 July 1817, Angostura fell to Bolívar's forces, which gained control of the Orinoco River in early August. Angostura became the provisional Republican capital and in September, Bolívar began creating formal political and military structures for the republic. Following a meeting at San Juan de Payara on 30 January 1818, Páez recognized Bolívar as supreme leader. In February 1818, the Republicans moved north and took Calabozo, where they defeated Morillo, who had returned to Venezuela a year earlier after conquering Republican New Granada. Bolívar next advanced towards Caracas, but was defeated while en route at the Third Battle of La Puerta on 16 March. He escaped assassination by Spanish infiltrators in April. Illness and additional Republican defeats obliged Bolívar to return to Angostura in May. For the rest of the year, he focused on administering the republic, rebuilding its armed forces, and organizing elections for a national congress that would meet in 1819.