Most pirates lived from voyage to voyage, plundering a ship before heading back to port to spend their share of the booty on booze, gambling, and wenches. There were a few, however, who either saved and invested their shares or made a huge haul or two and then retired to live off their wealth. While those who used piracy to go from rags to riches are the exceptions to the rule, they did exist and some of them lived out their lives in the lap of luxury. Buccaneer Henry Morgan and Red Legs Greaves are two of the more famous pirate success stories, but other pirates including Robert Surcouf, Henry Jennings, and Nathaniel North also found prosperity in their piratical careers.

Robert Surcouf

Robert Surcouf was a French privateer operating in the late 1700s and early 1800s. After beginning his career as captain of a French slave ship, he moved on to piracy, capturing several ships in the West Indies but losing his share of booty to the government because he didn't have a letter of marque. After securing one from France, Surcouf continued disrupting British shipping in the Indian Ocean. He captured nearly fifty vessels during his career, and later acted as advisor to Napoleon Bonaparte on matters of naval strategy. Surcouf died wealthy and well-respected among his peers, and was even escorted to his burial at sea by a flotilla of fifty sailboats.

Henry Jennings

Henry Jennings spent two years, from 1715 to 1717, as a British privateer operating under a license from the Jamaican government. In July 1715, Jennings led 300 men and three ships in a raid against a salvage crew working the wreckage of a Spanish treasure fleet that went down during a hurricane. Jennings and his crew defeated the salvagers and liberated the 350,000 pesos' worth of treasure recovered from the wreck. On their way back to Jamaica, they attacked and captured another Spanish ship and its cargo, which was worth another 60,000 pesos. Jennings continued to capture rich prizes for another two years, then accepted a pardon from the British government in 1717 and comfortably lived out his life in Bermuda.

Nathaniel North

In contrast to Henry Jennings, Nathaniel North was a seaman who spent his pirate years working on other captains' ships. His ability to swim (which was unusual at the time — even for pirates) saved his life on more than one occasion. North earned enough wealth during his years on the sea to retire to Madagascar, where he acquired an estate and “several wives and children,” staying there until he was killed while trying to settle a dispute among native tribesmen.

Others who made their fortune from piracy include:

John (James) Plantain: A Jamaican-born pirate who sailed the Indian Sea in the 1720s, then built a fortress at Ranter Bay, Madagascar. Plantain declared himself the “King of Ranter Bay” and lived a lavish life.

John Taylor: After beginning his piratical career sailing with Edward England, Taylor went on to captain the Victory and capture the Virgim de Cabo and her treasure, which was worth over £100 million plus enough small diamonds for each crewmember to receive his share of forty-two stones.

Rene Duguay-Trouin: A French corsair who sailed in the early 1700s, Duguay-Trouin captured over 300 British ships during his career, and was made an admiral in the French navy after capturing and ransoming the governor of Rio de Janeiro for an amount that doubled all of his investors' money.

Thomas Dover: After sailing as ship's surgeon with Woodes Rogers, Dover was given command of the Bachelor in 1709. A year later he attacked the Acapulco and captured a prize worth £1 million. He retired to London and spent the next thirty years creating and selling medical powders.

Thomas Pound: In Boston in 1689, Pound began his pirating career with a small fishing boat. He went on to capture larger and larger ships, and by the time he retired to a life as a gentleman in London in 1699, he was worth over £200,000.