Captain Pierre Le Grand(Peter the Great), around 1660-80?
Possibly the first “pirate of the Caribbean”, Pierre Le Grand was known among the English buccaneers as Peter the Great. His real name is not known.
Possibly born in Dieppe, France, Pierre was a privateer turned pirate who set out on the account with a small band of pirates. Stealing a skiff he and his men set out to board a larger ship and work their way up to the grand prize, a Spanish Galleon. After months of failure, Pierre and his men, half starved came upon a flota. Night had fallen and one of the galleons had fallen behind the others. Out of desperation Pierre devised a plan where they would bring the skiff up to the stern of the galleon and slip on board as quietly as possible.
To make sure his men knew that they must succeed, he drilled a hole in the bottom of his skiff so that it would sink. The men quickly scrambled onboard the galleon, killed the sleeping watch and then killed or captured all the officers, seized the gun room, and proceeded to round up the surprised crew.
The attack had been a complete surprise and success. Knowing he could never hold the entire crew, he dumped most of the crew and the officers on a nearby island keeping only enough Spaniards to round out a skeleton crew.
He then sailed the captured galleon and its treasure back to France, where he promptly retired. It is believed that Pierre le Grand was the first pirate of Tortugas and is often consider the first "True Pirate of the Caribbean" This particular act of piracy became the folklore of the islands which prompted many buccaneers to also go "on the account".
* A full account of Pierre le Grand is given by Exquemelin. Like many of Exquemelin's account this one is suspect. While Exquemelin states he only wrote about people he met and nothing is heresay, this account is suspect for three reasons..
What is true is the way in which Pierre le Grand would have started his career as a pirate and the method used to attack a ship.