The Ten Best Pirate Attacks in History

The Greatest Pirate Moments

The life of a pirate was a hard one: they were hanged if caught, they had to fight and torture victims to find their treasure, and discipline could be harsh. Piracy could occasionally pay off, though…sometimes big time! Here are ten defining moments from the age of piracy.

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Howell Davis Captures a Fort

Howell Davis. Artist Unknown

Howell Davis was one of the cleverest pirates in history, preferring tricks to violence. In 1718, Captain Davis decided to sack Gambia Castle, an English fort on the coast of Africa. Rather than attack with cannons, her devised a trick. Posing as a wealthy merchant looking to buy slaves, he gained the trust of the castle commander. Invited to the castle, he positioned his men between the castle guards and their weapons. Suddenly, he pulled a pistol on the commander and his men took the castle without firing a shot. The merry pirates locked up the soldiers, drank all the alcohol in the castle, fired the fort’s cannons for fun and made off with 2,000 pounds of silver.

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Charles Vane Fires on the Governor

Charles Vane. Artist Unknown

In July of 1718, Woodes Rogers, a tough former privateer, was sent by the British government to put an end to the plague of piracy in the Caribbean. Of course, local pirate hothead Charles Vane had to give him a proper welcome, which he did: firing on the governor's ship as it entered Nassau harbor. After stalling for time, later that evening Vane sent a burning fireship after the governor's flagship and fired on him again before making off into the night. Rogers would have the last laugh: Vane was captured within the year and hanged at Port Royal.

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Henry Jennings Loots a Sunken Fleet

Then the Real Fight Began. Painting by Howard Pyle (circa 1900)

On July 19, 1715, a massive Spanish treasure fleet consisting of ten galleons loaded with treasure and their escort of warships was caught by a hurricane off of Florida and utterly destroyed. About half of the Spanish sailors survived, washed up on the shore, and they hurriedly began collecting as much of the scattered treasure as they could. News traveled fast of the Spanish misfortune, and every pirate in the Caribbean soon made a beeline for the Florida coast. First to arrive was Captain Henry Jennings (among whose men was a promising young pirate named Charles Vane), who promptly sacked the Spanish salvage camp, making off with £87,000 worth of silver without firing a shot.

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Calico Jack Steals a Sloop

Calico Jack Rackham. 18th Century Woodcut, Artist Unknown

Things looked grim for Calico Jack Rackham. He and his men had anchored in a secluded bay on Cuba to take on supplies when a massive Spanish gunboat appeared. The Spanish had already captured a small English sloop, which they were keeping as it had been illegally in Spanish waters. The tide was low, so the Spanish couldn’t get at Rackham and his pirates that day, so the warship blocked his exit and waited for morning. In the dead of night Rackham and his men rowed over to the captive English ship and silently overcame the Spanish on board. When morning came, the Spanish began blasting Rackham’s old ship, now empty, while Calico Jack and his crew sailed out from right under their noses!

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Blackbeard Blockades Charleston

Edward "Blackbeard" Teach. Artist Unknown

In April of 1718, Edward "Blackbeard" Teach realized that the wealthy port of Charleston was basically undefended. He parked his massive warship, the Queen Anne's Revenge, just outside of the harbor entrance. He soon captured a handful of ships entering or leaving the harbor. Blackbeard sent word to the town leaders that he was holding the town (as well as the men and women on board the ships he had captured) ransom. A few days later the ransom was paid: a chest of medicines.

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Captain Morgan sacks Portobello

The Sack of Panama by Henry Morgan. Getty Images / Hulton Archive

Captain Henry Morgan, a very clever pirate, is the only one to appear on this list twice. On July 10, 1668, the legendary Captain Morgan and a small army of buccaneers attacked the unsuspecting Spanish port of Portobello. Morgan and his 500 men quickly overwhelmed the defenses and looted the town. Once the town was looted, they sent a message to the Spanish governor of Panama, demanding a ransom for Portobello…or they would burn it to the ground! The Spanish paid, the buccaneers divided the loot and the ransom, and Morgan's reputation as the greatest of the Privateers was cemented.

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Sir Francis Drake Takes Nuestra Señora de la Concepción

Sir Francis Drake. Artist Unknown

Sir Francis Drake had many famous exploits against the Spanish and it's hard to name just one, but his taking of the treasure ship

Nuestra Señora de la Concepción
Golden Hind

, caught up with the Concepción on March 1, 1579. Posing as a merchant, Drake was able to come right up beside the Concepción before opening fire. The Spanish were stunned and the pirates boarded them before they knew what was happening. Drake captured the prize with barely a fight. The amount of treasure on board was mind-boggling: it took six days to unload it all. When he brought the treasure back to England, Queen Elizabeth I made him a knight.

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Long Ben Avery Makes a Big Score

Henry Avery. Artist Unknown

Henry "Long Ben" Avery was destined to have a short pirating career. In July of 1695, only about a year after leading a mutiny which led to his becoming a pirate and acquiring a ship, Avery caught up with the Ganj-i-Sawai, the treasure ship of the Moghul Prince of India, which he promptly attacked and sacked. It was one of the single richest hauls in the history of piracy. The ship was weighed down with wealth beyond the wildest dreams of the pirates, who made their way back to the Caribbean and retired. Tales at the time said that Avery had started his own kingdom with his wealth, but it's more likely that he lost his money and died poor.

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Captain Morgan Makes a Smooth Getaway

Sir Henry Morgan. Artist Unknown

In 1669, Captain Henry Morgan and his buccaneers entered Lake Maracaibo, which is attached to the Atlantic Ocean by a narrow channel. They spent a couple of weeks raiding the Spanish towns around the lake, but they lingered too long. A Spanish admiral showed up with three warships and re-occupied a fortress on the channel. Morgan was cornered. Morgan then outsmarted his Spanish counterpart twice. First, he feigned an attack on the Spanish flagship, but in reality the largest of his ships had been filled with powder and blew the enemy ship to bits. Another one of the Spanish ships was captured and the third ran aground and was destroyed. Then Morgan pretended to send men ashore, and when the Spaniards in the fortress moved the cannons to fight off this threat, Morgan and his ships calmly drifted past it one night with the tide. Morgan got away without a scratch and with all the treasure!

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“Black Bart” Picks his Prize

Bartholomew "Black Bart" Roberts. Engraving by Benjamin Cole (1695-1766)

was the greatest of the Golden Age Pirates, and it's easy to see why. One day he was sailing off the coast of Brazil when he came upon an enormous fleet of 42 ships guarded by two massive men o'war, each packing 70 cannons: it was the annual Portuguese treasure fleet. Roberts casually joined the fleet and that night captured one of the ships without raising any alarm. His captives pointed out the richest ship in the convoy and the next day Roberts sailed up to it and swiftly attacked. Before anyone knew what was happening, Roberts' men had captured the treasure ship and both ships sailed off! The mighty escorts gave chase but were not quick enough: Roberts got away.