10 Most Successful Pirate Captains

Pirate top list

Famous pirate captains managed over their plundering careers to change the seas, driving fear into the hearts of not only merchants and sailors but also people living in large coastal cities that were often under the target of raiders. The golden age of piracy which lasted between the middle of 17th and early 18th century saw several waves of new pirate fleets, and during that time numerous pirate captains managed to distinguish themselves by the amount of money they amassed, their battle ferocity, personalities, and even their theatricality.

All the names on this list deserve to be remembered in history as the leaders of the vilest pirate crews of all time which managed to successfully raid ships on the seas of Carrie bean, West Africa, and India. No two pirate captains were the same, and they commanded anywhere between a single small ship to large pirate fleets. While they managed to capture a lot of wealth, the fates of almost all of these pirate captains were sealed by authorities, leaving precious few to live to old age and enjoy their captured wealth in full.

10. William Kidd (Scottish, 1645 – 1701)

Picture Of William Kidd
Public domain

A 18th century portrait of pirate William Kidd by Sir James Thornhill.

William Kidd was famous Scottish privateer who has crossed the line into piracy. Most of the pirate captain's achievements came in his "legitimate days" while he was battling pirates and the French army in the West Indies. Captain Kidd moved to the colony of New York when he was five-years-old, and when he was around 40s, Captain Kidd became an elite citizen and one of the best privateers in his time. His remarkable success was the conquest of Mariegalante where Captain Kidd captured booty worth more than £2000.

William Kidd's also started well when his new crew turned him into the pirate captain. Kidd captured famous ship called the "Quedah Merchant," but later he failed miserably.

9. Francois L'Ollonais (French, 1635 - 1668)

Picture Of François l'Olonnais
Public domain

François l'Olonnais the Bucaneer.

Outrageous French buccaneer who was best known for his cruelties was also very successful as he captured many ships and raided numerous towns. This pirate was probably one of the most successful captains who ordered land attacks. He raided cities Maracaibo and Gibraltar in the Gulf of Venezuela and later with great sea-power and with over 700 buccaneers he quickly captured the port of Puerto Cabello. Captain L'Ollonais died while attempting a raid on another rich town, San Pedro.

8. Blackbeard (English, 1680 - 1718)

Picture Of Blackbeard
Public domain

Blackbeard in the General History of the Pyrates.

Maybe Edward Teach aka Blackbeard was not as successful as other pirate captains on this list but his post-fame and his villain figure in today's fiction made every one of his deeds look even more fascinating. Blackbeard's notable successes were capturing many ships including the "Concorde" that became his flagship "Queen Anne's Revenge" and this vessel is perhaps most famous pirate ship ever.

This pirate captain also captured sloop "Adventure" and acquired sloop "Revenge" from pirate Stede Bonnet. When his fleet was most potent, with four ships and up to 300 pirates, Captain Blackbeard defeated famous warship, HMS "Scarborough" in sea-battle as well as many other British ships throughout 1718.

7. Henry Every (English, 1653 - ?)

Picture Of Henry Every

An 18th-century depiction of pirate Henry Every.

Captain Henry Every was a very successful pirate, in his time he was one of the most feared pirates of the Red Sea. With his fleet of 5 ships and crew of very experienced pirates, he captured many ships including famous Grand Moghul's "Gang-i-Sawai". However, the fact that he was very famous pirate captain and that he has managed to stay alive and retire peacefully is very rare achievement amongst pirates.

6. Cheung Po Tsai (Chinese, Early 1800s - Mid 1800s)

Picture Of Cheung Po Tsai Pirate
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Picture of Cheung Po Tsai a 19th-century Chinese pirate.

Cheung Po Tsai, a fisherman's son and a later pirate captain was best known and prosperous Chinese pirate during the 19th century. In the height of Cheung's power, his fleet counted an army of 20,000 men and several hundred ships. Cheung Po Tsai collected enormous treasure that was later found in a small cave. Today, that cave is named after him.

5. Peter Easton (English, 1570 – 1620)

Interesting fact about Peter Easton is that he is not well-known as other pirate captains on this list, despite all of his success. Captain Easton was a servant of the English Crown, who turned to piracy. He was best known as pirate captain who was never defeated by anyone commissioned to hunt him down.

His vast and powerful fleet counted 40 ships and over 1500 men in the height of his power. Peter's most significant victory came in 1610 in Newfoundland against Sir Richard Whitbourne's fleet as he defeated 30 ships. He also captured many prize ships including famous Spanish ship "San Sebastian".

4. Sir Henry Morgan (Welsh, 1635 - 1688)

Picture Of Henry Morgan
Public domain

Henry Morgan Welsh buccaneer.

Famous fearsome captain, Henry Morgan was a pride of Great Britain. Morgan success came when he arrived on Jamaica as England’s naval soldier. He made the first right step by joining a famous buccaneer, Captain Christopher Myngs in the conquest of Spanish colonies Vildemos, Trujillo, and Granada. With his success and good connections on Jamaica, he quickly became the leader of Jamaican fleet.

With his new ranks Captain Morgan first successfully raided coast od Yutacan Peninsula and the wealthy town Granada in Central America. In 1677, he captured Puerto Principe in Cuba and straight after a well-guarded town Puerto Bello. In 1669, with he conquered the city of Maracaibo in Venezuela. However, his biggest achievement was the capture of Panama City, one of the richest city of that time, with 1200 Buccaneers and 30 ships in truly epic battle.

3. Bartholomew Roberts (Welsh, 1682 - 1722)

Picture Of Bartholomew Roberts
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Bartholomew Roberts with his sword.

Welsh pirate, Bartholomew "Black Bart" Roberts was probably last great pirate captain of Golden Age of Pirates but also the most successful one. This cold-blooded pirate was best known for plundering more than 400 ships which is absolute record amongst pirates.

Captain Roberts burned or sold most of these vessels and only exceptions were superior ships such as two warships, both named "Royal Fortune" with 26 and 52 cannons and Royal Africa Company's prize ship, the "Onslow". He died in legendary battle against British Government's Captain Challoner Ogle.

2. Sir Francis Drake (English, 1540 – 1596)

Picture Of Sir Francis Drake
Public domain

SirFrancis Drake English, an sea captain, privateer, navigator, slaver, and politician of the Elizabethan era.

Sir Francis Drake was the most famous privateer and one of the most notable sailors in the history of the world. Captain Drake played the most significant role in creating a role-model for pirates in the Golden Age of Pirates. He was an English hero because of his achievements, however to Spaniards he was nothing but the most hated pirate captain as he devastated Spanish army on many occasions.

Drake’s most famous conquest was on the port of Nombre de Dios in 1572 and ports of Santo Domingo and Cartagena in 1585. Captain Drake is probably even more famous for sailing around the world, and when he landed on Pacific coast of North America, he Claimed the land for the English Queen and called it Nova Albion or the "New England."

1. Cheng I Sao (Chinese, 1785 – 1844)

Ching Shih
Public domain

Now merge all ships and vessels of previous nine pirate captains in this list, then gather all pirates and sailors they had, and you couldn't have nearly enough power to beat a mighty fleet of beautiful captain, Cheng I Sao.

In the height of her power, former prostitute controlled more than 1,500 ships and had the manpower of 80,000 sailors which was one of the biggest naval armies in the history of the world. This female pirate captain used her super large army for robbing and taxing towns and plundering ships throughout the coast of the South China Sea.

Picture Of Sir Francis Drake Privateer