Which are the most successful pirates in history?
The life of pirates is idolatrized these days – they got to sail the seas, say “argh” a lot, they wear eye patches and have glamorous lives seeking adventure. In recent years, it has been the fault of movies such as “Pirates of the Caribbean” for this and Johnny Depp’s allure, but reality is far from what this type of movies portray it. The likes of “Black Sails” actually put the life of the pirates in a more accurate light, although there’s still plenty of Hollywood in that series too.
The era of the high seas piracy was ruthless, and many buccaneers lost their lives during the many plunders they took part in. It was part of the job description, of course, but the number of ocean graves was still extremely high. Whether it was the Caribbean seas or the Chinese ones, pirates made sure to go after everything they could, be it gold, silver or various goods like tea and jewels.
If you are more interest in the modern type of criminal, don’t miss our article on countries with most hackers and cyber criminals.
Back on the main topic – in order to determine which of the world’s many pirates were the most successful we took a look around the Internet, checking out multiple lists, on sites such as The Way of the Pirates and History Lists to name a few. Each pirate got a mention for each site they were on, with a maximum of 7. The lists we checked out were related to success, because being successful doesn’t just mean getting the biggest plunders, but also being feared and famous.
Then, we checked out one of Forbes’ lists where the wealth of the pirates was translated to into today’s money, with as much accuracy as possible, given the fact that these buccaneers were alive between 1500 and 1700. Depending on how much wealth they gathered, the pirates then received extra points, leading to our final list of most successful pirates in history. It should also be mentioned that in the case of a tie, the pirate with the larger wealth got the better spot, since, after all, the financial success of their pirating ways does tell a lot more than how many times they were mentioned on various lists. Without further ado, here are the 10 most successful pirates in history.
10. Henry Avery
Mentions – 5
Wealth – 0 points (unknown)
Total – 5
Henry Avery (also Evory, or Every) lived somewhere in late 1600. Since data keeping at the time is rusty at best, we’re just going to take the ones we’re being offered by various online sources. The English-born pirate operated in the Atlantic and the Indian oceans, looting left and right under various nicknames, including Benjamin Bridgeman and Long Ben.
What made Avery stand out? Well, it must be the fact that he managed to retire without getting killed or imprisoned, which means he left his fleet behind with quite some money in his pockets. It is also said that he only activated as a pirate for a couple of years, but his skills brought him quite a bit of fame.
9. Thomas White
Mentions – 1
Wealth – 4 points ($16 million)
Total – 5 points
During the first half of the 18th century lived Thomas White, the number 9 in our list of most successful pirates in history, born in Plymouth. Starting out in life with a great education didn’t seem to steer this young fellow to better jobs. The fact that he was attracted to the sea ultimately led him to life as a pirate. Starting out aboard a warship, he ended up in the Barbados where he eventually set roots, marrying.
After several years he ended up a pirate on a ship under Thomas Howard, a pirate active in the Indian Ocean and the Red Sea, before moving on to Thomas Halsey’s ship. Their preferred targets were ships full of spices, fruits, and animals that were uncommon in the European area.
8. Jean Fleury
Mentions – 1
Wealth – 5 ($31.5 million)
Total – 6 points
While Jean Fleury isn’t that well known of a name, his feat surely is. Back in the 1500s, when Cortes reached Mexico managing to decimate the Aztecs in the process by bringing smallpox on his ships, Fleury was at sea, looking for loot. Lo and behold, came Cortes’ ships full of Aztec gold, ready for the taking. Well, not that “ready” per se, since there were fights, but you get the point. Fleury managed to steal 2 out of 3 treasure ship from the fleet, making tens of millions of dollars in gold.
Along with the gold came heaps of jade, jewelry, emeralds, pearls, work of art and more, which were taken to King Francis I.
7. Blackbeard
Mentions – 6
Wealth – 1 ($12.5 million)
Total – 7 points
We are continuing our list of most successful pirates in history with Edward Teach, who is an English pirate born around 1680. While this name may sound a bell or two, it’s his alias that made him famous – Blackbeard. His favorite areas to plunder were the waters around the West Indies and the eastern coast of the American colonies. He started out as a sailor before ending up under Captain Benjamin Hornigold’s command whom he sailed with until 1717 when Hornigold is said to have retired. Teach continued on the piracy journey, taking ship after ship and becoming one of the most feared names of the time.
His plunders were definitely fruitful since his wealth reached an estimated $12.5 million by the time of his death.
6. Captain Henry Morgan
Mentions – 5
Wealth – 3 ($13 million)
Total – 8 points
This welsh pirate who ranks 6th in our list of most successful pirates in history sure made a fortune in his lifetime. Reaching some $13 million in today’s money, Captain Morgan earned his place among the best of the best. Once an admiral of the Royal Navy, Morgan raided ships on the side, supplementing his income by taking from the Spanish. Not only is his reputation as of one of the most notorious and successful pirates in history, but he was also known as one of the most ruthless of his time. Nowadays, you might know Captain Morgan better if you’re a fan of drinking rum.
5. John Bowen
Mentions – 1
Wealth – 7 ($40 million)
Total – 8 points
Born in the Bermuda area, John Bowen had a rather short “career” as a pirate, activating as a buccaneer for only four years before his death in 1704.
In the beginning, he was a crew member of Captain Read, but soon joined George Booth’s crew before becoming the Captain of the Speaker, a 450-ton former slave ship with some 50 guns aboard. He attacked many ships, including of English origin, until the Speaker was taken by the Ocean in 1701. Later, he managed to seize another ship and, over the years, changed quite a few of them, choosing to burn them to the ground when they no longer suited his needs. After making a fortune, Bowen decided to retire, but his wealth didn’t get to be enjoyed. The pirate died within a few months, in 1704, of some sort of intestinal disease.
4. Thomas Tew
Mentions – 3
Wealth – 8 ($103 million)
Total – 11 points
Known as the Rhode Island Pirate, Thomas Tew, the next one in our list of most successful pirates in history, is an English privateer that turned pirate. Born in the 1600s, Tew had quite a few successful attempts to take over ships taking trips around the horn of Africa and towards the Indian Ocean. He managed to steal over $100 million in gold and various other treasures throughout his time as a pirate.
As many others on the list, he didn’t really have the chance to enjoy the money he stole. In 1695 he tried to pursue a 25 ship convoy, attacking one of them. Tew was killed in the battle, reports at the time indicating a horrendous death following being shot by a cannon.
3. Black Sam
Mentions – 2
Wealth – 10 ($120 million)
Total – 12 points
Born in the late 1600s, Captain Samuel Bellamy made a name for himself as Black Sam. Although his career as a pirate captain lasted just a little over a year, he was one of the most successful buccaneers to ever set sail, amassing a wealth estimated by Forbes at some $120 million. How was that possible? Well, during his short stint as a pirate of the seas, Black Sam captured at least 53 ships.
Other than his reputation as one of the most successful pirates in history, Black Sam was also often named the “Prince of Pirates” because he always showed mercy and generosity towards those he captured in his raids.
Much like Blackbeard, Black Sam started his journey as a pirate alongside Benjamin Hornigold’s crew and later sailed with Blackbeard himself on the Marianne.
His wealth was not enjoyed, however, as the ship he was on, the Whydah, was a victim of a violent storm off Cape Cod as Black Sam tried to reach his family. All but two of the 145-man crew was washed ashore days later.
2. Black Bart
Mentions – 7
Wealth – 6 ($32 million)
Total – 13 points
Bartholomew Roberts ranks second in our list of most successful pirates in history. He was a Welsh pirate born in 1682 who was known for raiding ship near the Americas the West Africa. While his “career” as a pirate didn’t last very long, he managed to amass a wealth of some $32 million in today’s money, by Forbes’ calculations.
While the moniker of Black Bart is often used to refer to him, it was never actually used during his lifetime, especially since there was another pirate going by that name. Bartholomew Roberts sailed for much of his life, before ending up as a pirate, raiding ships going back and forth between Africa and the Americas. Whether it was in his crew’s pockets or at the bottom of the ocean, his wealth vanished after his death in 1722 during a battle with one of the Royal Navy’s ships.
1. Sir Francis Drake
Mentions – 4
Wealth – 9 ($115 million)
Total – 13 points
Sir Francis Drake was born in 1540 by some records, and he spent his life at sea, as a captain, privateer, navigator, and slaver, while also playing the role of a politician. He is best known for being the second to circumnavigate the world in a single expedition, between 1577 and 1580.
Drake wasn’t the typical pirate, like you see in the movies, mainly because he was fully backed by the English. While the Spanish certainly hated him and called him a pirate after taking over several of their ships and their treasures, he was a hero to the English, with Elizabeth I of England awarding him a knighthood in 1581. In fact, the Spanish hated him so much they put a bounty on his head, one that was never claimed.
As vice-admiral in command of the English fleet, Drake managed to overcome the Spanish Armada trying to invade England back in 1588, going as far as to capture the Spanish galleon Rosario.
Drake’s last big fight ended in defeat as Spanish ships shot a cannonball into his cabin, although he survived that attack. Weeks later, however, he died of dysentery. Drake was feared, famous and successful, putting him at the top of our list of the 10 most successful pirates in history.
