Diego Grillo: The First Cuban Pirate

The Cuban archipelago was a strategic location for the pirate action. However, not only Cuba was victim of the vandalism of those foreigners that used to plunder the wealth of this young Spanish colony. This land also had its own killers. Diego Grillo was the first pirate to be born in this island who was very well known worldwide.

The story tells that for a long time it was widely believed that Diego Grillo was missing, but, he appears in England as a wealthy business person.

Accompanied in the taverns with his old fellow sailors, he recalls the adventures that led him to become a legendary personage: the first and most notorious of all pirates born in Cuba.
Seeing the horizon line on the sea, he evoked the bloody battles, the damages caused in the American waters during the last quarter of the 16th century and a good deal of the 17th century too.

The beginnings

It looks that everything began when a Spanish conqueror in his voyage to "terra firma" met a young and sensual African slave woman. Diego Grillo was born from that union in Havana by 1555. Considered one of the most controversial figures of piracy's history, born slave like his mother, Diego which was also known as "El Mulato," escaped when he was 13 years old and found shelter in the mangrove swamps. There, he waited for a scope to flee from captivity once and for all. Afterwards, he joined a band of Spanish buccaneers that trafficked in the Caribbean Sea.

Francis Drake: His protector

After four years sailing through the waters of the Mexican Gulf and the Caribbean Sea, when he had gotten certain experience as sailor, Diego is captured by pirate Francis Drake near the Isle of Pines, Cuba in 1572.
His adventurous fearless spirit, his bold resolution and his defiant attitude expressed in the way he looked at people, inspiring respect among those who faced him, seemed to have convinced the terrible "thief of the seas" on how valuable would be to have such a man in his crew. So Drake took Diego Grillo under his protection and brought the youngster to England.

Already in Europe, the Cuban pirate fights under the commands of the Count of Essex and other English gentlemen. When he was 22 year old, Diego Grillo became the court's favorite man, being welcomed by the Monarchs themselves who confer him various honors for his duties to the British crown.
After five years in England, he returns to the Caribbean in an expedition organized by Drake. On that trip he was the second in charge.

Time did not pass too much when Diego Grillo became the boss of that mission. In 1595, when his protector died, the Cuban pirate came back to England, with gold and fame traveling with him.

The last raid

After a break from Sea adventures, Diego appears in the Antilles accompanied by Cornelio Jols, nicknamed "Wooden Leg". This was considered one of the bloodiest unions in the piracy history. Some many Spanish ships felt their strength; they took almost the whole crewmembers prisoners.
In his adventures, Diego Grillo makes one of the greatest exploits in piracy history by capturing an 11 ships convoy.

For any one else this could have been enough to take it off amassing a tremendous wealth and fame, but not for Diego Grillo. The infamous pirate wanted to make his "last raid".
Nuevitas' harbor, north Camagüey province, was the haven of the ships that sailed to Spain loaded with plenty of treasure.

It is said that he and his men attacked Spanish ships from a fifteen-gun ship and sold the booty in Tortuga. Three ships were sent to capture him, but he defeated them all and slaughtered every sailor aboard who had been born in Spain.
In 1619, after having meticulously planned the assault, Grillo took a six frigate convoy by surprise in the entrance of that harbor. The filibusters won that battle and most of the Spanish crew died.

The spoils of that assault seemed to have been very substantial because he was not longer seen in the Caribbean Sea and there were people who believed he disappeared some miles off Nuevitas' coasts.
Up to now the final history of the first Cuban pirate remains uncertain as some sources refers that he was captured in 1673 and hanged meanwhile some others believe that Diego Grillo settled down in England, enjoying forever his condition of being the "first Cuban pirate". (Translation: Gualveris Rosales).


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