These days, it seems like the only rich and famous pirates and buccaneers are big-contract professional athletes. The trade of a traditional seafaring pirate was a potentially lucrative endeavor between the 17th and 18th centuries. However, it was only lucrative for the hardened few who could withstand scurvy, sword fights and the cannon fire of various navies. Not only were some of these men brave, cunning and ruthless enough to lead crews of cutthroats through the high seas, but they were shrewd businessmen as well. While most pirates died young and penniless, some of the more successful buccaneers looted enough booty to amass impressive personal fortunes.
Samuel Bellamy: $129 million
"Black Sam" was the wealthiest pirate of all time, boasting a personal fortune that was estimated to have been worth almost $129 million in 2012 dollars. In the early 1700s, Samuel Bellamy was just a struggling sailor when he decided to become a treasure hunter in the hopes of recovering lost fortunes from shipwrecks. Unfortunately, most of the treasures were already recovered by navies that were better manned and equipped. In 1716, Bellamy joined forces with friend Palgrave Williams and they became buccaneers. Bellamy was elected as commander of a pirate fleet later that year.
Bellamy led his crew in raiding more than 50 ships in the Caribbean and the Atlantic between 1716 and 1717. In February 1717, his crew captured the Whydah, which was a British slave ship. They seized over 20,000 pounds of sterling and a fortune in gold and other goods for trading. Bellamy made the Whydah his flagship. Only two months later, Black Sam Bellamy drowned, sinking with his prized ship. Ultimately, it was not a navy that defeated Black Sam but rather a violent storm. Bellamy was only 28 when he died, but he plundered enough ships to become the richest pirate ever, and he did it all in little more than a year.
Sir Francis Drake: $123.6 million
As his knighthood suggests, Sir Francis Drake was a highly-respected public figure in England. He served as a sea captain, navigator, politician and even a human trafficker. To the English, Drake was a privateer, which is a civilian licensed by a government to attack and capture enemy cargo ships in exchange for prize money. To the Spanish, however, Drake was one of the most notorious buccaneers on the high seas. Drake's first major foray into piracy came in 1572 when he and his men captured the town of Nombre de Dios, Panama. The Spanish-held town had just received a large shipment of gold and silver from Peru, and Drake and his men helped themselves to the treasures. He spent the better part of a year plaguing Spanish shipping in that region.
In 1573, Drake attacked a mule train and seized roughly 20 tons of silver and gold. However, since Drake and his men were unable to transport all that treasure safely, they opted to bury it. This likely inspired all the famed tales of "buried pirate treasure." Unlike Bellamy, Drake managed to retire from piracy with a vast, if slightly smaller, fortune. Drake was knighted by Queen Elizabeth I in 1581 and was second-in-command of the English fleet that battled the Spanish Armada in 1588. Drake later served as the mayor of Plymouth, England. He died of dysentery in 1596 at the then-old age of 55.
Thomas Tew: $111 million
The "Rhode Island Pirate" was not only one of the wealthiest pirates in history but also one of the most influential. Thomas Tew is perhaps best known for being one of the first pirates to sail the "pirate round," which was a popular route for pirate ships that stretched from the North Atlantic to Madagascar.
In December 1692, while operating as a privateer in Bermuda, Tew was able to secure a 70-ton ship with eight guns and a crew of 46 people. His backers, including officials in Bermuda, believed that Tew was going to use the ship and crew to defend French holdings in Gambia, West Africa. Shortly after leaving, however, Tew made it known to his crew that he had no intention of sailing to Gambia. Instead, he wanted to use the ship for piracy. His crew supported his decision and agreed to become pirates as well.
In late 1693, Tew plundered a massive ship from India with a garrison of 300 soldiers. Surprisingly, the Indian ship's crew easily surrendered and Tew's men suffered zero casualties. From that ship, Tew and his men looted 100,000 pounds in gold and silver and a small fortune in ivory, spices, jewels and silk. Tew personally kept 8,000 pounds, while the men shared between 1,200 and 3,000 pounds each.
In September 1695, Thomas Tew joined up with some other large pirate ships on the Red Sea to pursue a 25-ship convoy belonging to the Mughal Empire. The unified pirate forces managed to capture at least one of the Mughals' ships, but Tew was killed in the battle. It is believed he was disemboweled by a cannon shot. Much like Bellamy, Tew's career as a pirate was lucrative and very short, as he only operated as a pirate for about three years.
The Bottom Line
The golden age of piracy saw some intrepid pirates loot and plunder their way to astonishing personal fortunes. All three of these men flourished during this era and earned unsurpassed fortunes in their illicit trade. Although Drake made powerful friends and managed to live a long, wealthy and prosperous life, Bellamy and Tew's lives were cut short as a result of their life-threatening careers. Seafaring piracy still exists, but it's less lucrative than in years past, and many of today's wealthiest criminals are of the white collar variety.