Venezuela and New Granada
In December 1811, Maria MacGregor died. By this time, MacGregor had heard about the independence movements in South America and the Captaincy General of Venezuela in particular. He sold his small Scottish estate and sailed for South America, arriving in Caracas in the spring of 1812. He talked General Francisco de Miranda, the Commander in Chief of the new Venezuelan Republic's army, into appointing him a colonel in the army, and almost immediately he was involved in a series of skirmishes that resulted in his promotion to brigadier-general. A month or so later, when General Miranda was captured and handed over to the royalist forces by Simon Bolívar, MacGregor fled to Curaçao on a British brig with his new wife.
During his brief stay in Caracas, MacGregor had met Josefa Antonia Andrea Aristeguieta y Lovera, the daughter of a prominent local family and a cousin of Simon Bolívar. They were married on 10 June 1812. They eventually had three children, Gregorio (b. ca. 1817), Constantino, (b. ca. 1819) and Josefa Anna Gregoria (b. ca. 1821), and their marriage endured twenty-six years, until Josefa's death in 1838.
From Curaçao, MacGregor decided to go to New Granada (present-day Colombia) and join the liberation forces of General Antonio Nariño. For Josefa's safety, he first took her to the British island of Jamaica and then sailed for Cartagena on the northern coast of New Granada. From there he made his way south to Tunja, where General Nariño put him in command of the military district of Socorro, near the Venezuelan border. During the year or so he spent here, he earned what became a lifelong reputation as an unreliable braggart. One local official wrote of him: "I am sick and tired of this bluffer, or Quixote, or the devil knows what. This man can hardly serve us in New Granada without heaping ten thousand embarassments upon us."
In 1814, the Spanish royalist forces routed General Nariño's army and MacGregor took refuge in Cartagena de Indias, where he played a role in organizing the city's defenses. In August 1815, the Spanish troops of General Pablo Morillo attacked the city and began a siege that lasted until December, when disease and starvation forced the city to surrender. On the night of 5 December, MacGregor helped to organize a mass escape aboard gunboats that blasted their way through the Spanish blockade and sailed for Jamaica.
In Jamaica, MacGregor was treated as a hero, but by the spring of 1816 he had moved on with Josefa to the neighboring island of Haiti, where Simon Bolívar was raising a new army. In April, MacGregor sailed with Bolívar's fleet as a brigadier-general to Venezuela, landing on the island of Margarita before crossing to Carupano on the mainland. Both Bolívar and MacGregor ran into trouble after their forces split up, and MacGregor's troops were eventually forced to retreat towards the town of Barcelona, fighting all the way. This difficult, month-long campaign earned MacGregor deserved acclaim and is probably the high point of his military adventures, which were otherwise marred by varying amounts of error, incompetency, and exaggeration on his part.
Read more about this topic: Gregor MacGregor