CubaPLUS Magazine

Diego Grillo, the “Cuban” pirate

By: Alina Veranes
Mar 07, 2023
Diego Grillo, the “Cuban” pirate

It is attributed that he was born in Havana around the year 1556 to become  the most famous pirate born in this land, a demoniac nicknamed Diego Grillo, although his real name could be Diego Martín.

He was also known as Dieguillo or the Mulatto Lucifer, which illustrates very well the nature of his adventures. They say he was the son of an Iberian man with a black slave woman, who at least was lucky enough to be baptized. But this did not save him in his childhood from the horrors of slavery in the service of the cruel governor of Campeche, where he ended up, who frequently whipped and imposed cruel punishments on him. The injustices forged a rebellious character in him and as soon as he could, he escaped from the place and managed to be accepted at the age of 13 as a cabin boy on a small-time Spanish frigate.

He was a sailor when two years later while working on a Spanish galleon, it was assaulted by the famous privateer Francis Drake, who passed it on to his crew of outlaws and made him his student of misdeeds. Dieguillo very soon felt that this life of adventures, attacks and wild looting was his thing. He admired Drake who, apparently, also took a liking to him.

The first thing the corsair did at the beginning was to take him on an assault on Nombre de Dios, Campeche and Veracruz, and that kind of revenge pleased the boy very much.For a few years he learned all he could from Drake and was a very gifted student.He spoke English perfectly and was very skillful and brave in battle, but unlike many pirates he developed a gentlemanly relationship with the women or ladies he took prisoners, not allowing mistreatment, having his own ship and commanding thatdangerous profession of vandalism and adventure.

When Drake was later appointed Admiral in England, The  Mulatto Lucifer bought his own ship and hired French, English and Dutch cronies.Several Caribbean and Cuban enclaves became frequent victims of his attacks and the Spanish found it difficult to repel the daring pirate.

They say that Diego ventured into the Caribbean again with Francis Drake around 1585, when he no longer held the position of Admiral.They tried to sack Puerto Cabello and Cartagena de Indias together, but they failed, as an epidemic of yellow fever decimated their formidable warriors or sea wolves.

Diego tried to attack Havana from Cabo de San Antonio but, apparently, they could not recover and he abandoned the plan. Nothing is heard of him again until February 18, 1603, when, to everyone's surprise, Captain Diego Grillo revives the picture of him having become almost a respectable man.

However, this coincides with the time when they begin to call him Mulatto Lucifer.At that time, he is linked to the Dutch privateer Cornelius Corneliszoon Jol, the famous Peg Leg, of whom he became second in command.He continues to champion the world of vandalism and piracy, attacking Santiago de Cuba and important enclaves on the island.

There are different versions about the death of the legendary pirate born on this island, when its inhabitants were not yet called Cubans, but Creoles in any case. One of these legends refers to the fact that he was captured and hanged by the Spanish in 1673, as he was closely persecuted by two governors of the Island. This was impossible, due to the age he must have been at that time, even though he was Lucifer himself among humans.

This is how certain legends are, made with myths and realities.

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