Diabolito orLittle Devil (died July 1823) was a 19th-century Cuban pirate. One of the more violent of the era, he engaged theUnited States Navy andRevenue Marine Service several times, being one of the main fugitives hunted and pursued later by American Naval forces during theWest Indies anti-piracy operations of the United States in theCaribbean during the 1820s. He was also known for having a mixed-race crew, which included “English, Frenchmen, Spaniards, Mulattoes, and Negroes.”

The Cuban-born Diabolito became known as a particularly dangerous pirate operating from his home island during the early 19th century. He among others includingCharles Gibbs, andRoberto Cofresí were identified as key figures in piracy when PresidentJames Monroe authorized the formation of an anti-piracy squadron to combat attacks on American shipping and naval forces occurring off the Florida coast. Based inKey West under CommodoreDavid Porter, a veteran of theFirst Barbary War, theSecond Barbary War, and theWar of 1812, the "Mosquito Fleet" soon began patrolling theGulf of Mexico and theCaribbean. Diabolito and other Cuban-based pirates were easily able to escape from American vessels, either escaping into the back country of theFlorida Keys or retreating to Cuba where Porter's forces were unable to pursue. As the years passed, however, Cuban ship owners and other businessmen petitioned for authorities to cooperate with the United States. Spanish officials were unable to continue turning a blind eye to piracy, which often amounted to attacks on lone merchant vessels and fishing boats, and agreed to assist in hunting down Diabolito and others.

In April 1823, Diabolito encountered Porter and was cornered off the northern coast of Cuba. After a brief fight, he and his crew abandoned their ships and fled inland.^[1] Out of his 70-man crew, 30 were either killed during the fighting or drowned while trying to swim to land. He managed to elude authorities and, acquiring another ship, he set sail for theYucatan. He again encountered the Mosquito Fleet when USSGallinipper and USSMosquito, commanded by Lieutenant William H. Watson and Lieutenant William Inman respectively, pursued him upon finding him in Cuba once again. Although the pirates outnumbered the Americans, whose total force numbered 31 men compared to the 70 or 80 pirates, Watson gave the order to attack and sailed towards the pirates, driving them into the sea. The men began abandoning their ship, the 4-gun schoonerCatalina, and the American vessels were "soon in the midst of the swimmers, and, laying about right and left, exterminated dozens of them". All of his men were either killed or were captured by local authorities, Diabolito himself being killed in the water when he refused to surrender.^[2]

• 1823 deaths
• 19th-century Cuban people
• 19th-century pirates
• Spanish pirates
• 19th-century Spanish criminals
• Piracy in the Caribbean

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