This piece was originally posted on Talk Like A Pirate Day 2008.
From Forbes:
High seas piracy was the colonial era’s version of investment banking. Through good positioning, aggressive go-getters could make millions from global trade and commerce in diverse sectors. They were frequently chased off shore to the Caribbean by angry governments. And in the end, they were sometimes sunk without a trace.*From gCaptain June 3: "Tanker Hijacking Part of Broader Pattern, Experts Warn"
Soon after government-hired pillagers like Hernando Cortes started plundering the new world in 1503, an entire class of sailor realized he could profit by stalking the ships carrying the spoils.
Those riches couldn’t be sent using wire transfers. So when Cortes wanted to send a bounty of Aztec gold to Charles V, he had to load it onto ships and sail it across the sea, where men like Jean Fleury were waiting. In 1523, the French privateer fell upon a Spanish treasure fleet–a score that helped him net $31.5 million in present-value dollars over his career, making him the sixth highest-earning pirate of all time.
The highest-earning pirate ever was Samuel “Black Sam” Bellamy, an Englishman who made his bones patrolling the New England coast in the 18th century. By our calculations, “Black Sam” plundered an estimated $120 million over the course of his career. His greatest windfall occurred in February of 1717, when he captured a slave ship called the Whydah, which reportedly held more than four and a half tons of gold and silver. Bellamy, known for his relative generosity, took the Whydah as his new flagship and gave one of his old vessels to the defeated crew.
In second place, with lifetime earnings of $115 million: Sir Francis Drake, a 16th century British privateer who saved England from the Spanish Armada and went on to a profitable life of plunder at the behest of Her Majesty’s Government. Fellow Englishman Thomas Tew places third with earnings of $102 million. His biggest score came in 1693, when he pilfered a ship full of gold en route to the Ottoman Empire from India.
Our wealth estimates are based on information gathered from historical records and accounts from 17th and 18th century sources like Daniel Defoe, as well as contemporary historians like David Cordingly. Whenever possible, we used official records of pirate’s claims. So when a 1718 North Carolina ledger says wares seized from Edward “Blackbeard” Teach sold at market for 2,500 pounds following his death, that source was trusted above Blackbeard’s claims to a magistrate that a great treasure lay in a location known only to him and the devil. By our count, he amassed a total of $12.5 million in loot over his career.
Depletion of fortune due to rum and wenches was not assessed, nor were divisions of treasure among the crew. Plunders were often split in equal shares, with the captain receiving double–not much of a premium for leadership. A good lesson to modern shareholders: The best way to achieve fair compensation and rule out golden parachutes is to have your leaders expecting murderous revolts if they hoard profits....MORE
