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The Isle of Pines and the pirate Pepe el Mallorcan

Until the mid-19th century, the Isle of Pines, a small island sitting in the mouth of Batabano Bay on the south side of Cuba, had a long yet mysterious history as a base for sea-raiders of all nations. Unlike its more famous pirate base cousin of Tortuga, ownership of the little island never fluctuated. It had belonged to Spain from the time it was first discovered by Christopher Columbus. However, even though it had superior colonisation prospects to other islands in the area, for 250 years it lay forgotten by the nation that laid claim to it.


The absence of any authority on the Isle of Pines, combined with its geographic location along the sailing route of the Spanish gold fleets, made the little island an excellent re-supply station for sea-raiders and pirates in need of timber and fresh water. Throughout the Caribbean era of piracy, the island was privately owned by Captain Hernando de Pedroso and his descendants. For at least a hundred years, the family did little with the land itself until the late 18th century when one of Pedroso’s relatives attempted to colonise it. By 1782, a 300-strong population supported itself making salted beef, yet the island never appeared in Spanish census records. By the early 19th century, the demise of the gold fleets and the shifting of sailing routes north of Cuba meant the significance of the Isle of Pines as an international sea-raiding outpost diminished. Nevertheless, it remained a refuge for those escaping the law, including a pirate who operated from there in the 1820s: Antonio “Pepe” el Mallorquin.


To the British and American merchants during the 1820s, Cuban-based sea-raiding was a significant problem. Unlike most of its neighbours, Cuba was not agitating for independence from Spain and considered Cuban raiders as Spanish patriots, not pirates. Cuba rejected any accusations of piracy from the British and Americans and refused to cooperate with their piracy suppression initiatives. Except when it came to Pepe.


From his base at the mouth of the Santa Fe river on the north-eastern coast of the island, Pepe commanded around 40 men and operated from La Barca, a schooner armed with one solitary cannon. Pepe focused his successful operation on targeting the small boats of the inhabitants of neighbouring islands and remote settlements in southern Cuba. For an unknown number of years, he was too small fry for the British and Americans because he did not attack their ships and of little concern to Cuba because all its neighbours were anti-Spain nationalists and therefore Spain's enemies. He operated with impunity until March 1824, when he was unexpectedly discovered by a handful of English vessels en route to Jamaica.


It is not entirely clear who attacked first. The English were actively interdicting pirates and slavers in the West Indies so its quite possible they recognised the nature of his operation and pre-emptively attacked. On the other hand, Pepe may have been unable to resist the allure of the more robust prize of English ships right in his territory, rather than the small, open boats he usually targeted. Whoever went first, in the ensuing melee, several pirates and six Englishmen died. According to the English language press, they suffered the indignity of being cold-bloodedly murdered on land rather than killed in action. The English sloop Icarus managed to destroy some of the pirate vessels before escaping to Port Royal to report the incident. From there, the British sought and received permission from the Cuban governor in Havana to destroy Pepe’s operation.


The British and Cubans, in an unprecedented collaboration for the time, sent a party of 300 to 400 men to pursue Pepe and his men. A pirate captured in the earlier raid helped guide them to the villages in return for a reprieve on a death sentence. The forces unleashed a firestorm that destroyed all the pirates’ boats and huts, yet the pirates themselves managed to escape into the island’s wild interior. A hundred men were detached up the Sante Fe river to hunt and kill them. According to one Spanish website, the pirates fought the English with tenacity and courage and with such a fierceness that it took a year to eliminate them. Pepe el Mallorquin’s hand was apparently destroyed when his blunderbuss (a type of gun) burst from ‘shooting so much at the English’. Out of firepower, he was forced deep into the bush to avoid capture where, ‘they say’, he founded a family and died after many years.


Of course, in true pirate tradition, the story sometimes goes that he was hanged from the main mast of the British captain’s ship. Another account swears he died from his wounds at the hands of the English and his head was removed and triumphantly returned to England. This one aligns more with the English version of events reported in The Times. According to them, Pepe’s body was quickly found in the bushes on the Isle of Pines, where he had apparently died of starvation. Given the British fascination with the study of phrenology to explain criminal behaviour at the time, the removal of the head part of the story is not outside the realms of possibility. The Times did not mention what became of his head.


Here the story of Pepe comes to an end. A few of his men were convicted of piracy in Jamaica but several of them escaped to regroup. An American lieutenant called Thomas W Freelons discovered about 20 of them re-settled on Cayo Romana, near the remote island of Guanaja (off the coast of modern Honduras). He attempted to capture them but was quickly thwarted by their willingness to open fire on him.


Pepe’s legacy was to force Havana into making a concerted effort to exert more authoritative control over the Isle of Pines. Spain appointed a succession of governors to the island until Cuba’s independence in 1898. By the 1920s, the island housed a brutal prison for political dissidents. Today, it is known as Isla de la Juventud (Isle of Youth), has a population of around 85,000 and is gearing towards the growing Cuban tourism industry.

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