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Pirates - Part 2

The Golden Age of Piracy: 1650-1740


Ahoy! Last time on Epik Fails of History, in The Golden Age of Piracy (Part One)I dispelled some persistent piratical myths, explained how piracy began in t’ Caribbean with legally sanctioned privateers like good ole’ Capn’ Morgan and his merry buccaneers, and told the two-sided tale o’ the infamous Long Ben’s exploits which smartly inspired an entire generation of me scurvy scoundrels…

So grab yer grog ye landlubbers as we dive back in ta Davy Jones’ Lockarrrr!

Pirate food pyramid


Nassau, the Capitol of Piracy in the Caribbean, was located on New Providence Island, in the Bahamas for those of you who failed geography. Prior to becoming a pirate haven, the island had been completely deserted after a relentless raid against English privateers by the Spanish in 1684, just because. Located near the Straits of Florida, New Providence was a perfect location for pirates to launch interception operations against treasure-stocked vessels bound for Spain.

In the words of Obi-Wan Kenobi, it became ‘a wretched hive of scum and villainy’.

The Pirate Bay (logo)

Henry Jennings was a former privateer and veteran of Queen Anne’s War who turned to piracy and later became the unofficial ‘mayor’ of Nassau, where he would eventually retire to a life of luxury, that is after going turncoat and hunting down his former brothers-in-arms. Long story short, Jennings was one of the first privateers to follow in Henry ‘Long Ben’ Avery’s legendary foot steps (see Part One for Avery’s adventures in the Indian Ocean).

In July of 1715, a treasure fleet of 12 Spanish galleons shipped out from Havana, Cuba.

evacuation plan

Welcome to Florida

11 of them never arrived at their destination, because on July 30th, 1715, the entire fleet of fully stocked treasure ships sailed head first into A GOD DAMN HURRICANE! The massive storm made quick work of the heavy wooden ships, drowning a thousand crewmen, and scattering their shinny plunder across the Floridian coast.

As word spread of the wreckage and wealth washing up on the shores of (Vero Beach) Florida, Jennings and his cohorts were the first on the scene to scavenge through the remains of the Spanish treasure trove. With the help of his pupil, Charles Vane, Jennings brought home £87,000 in gold and silver from an assault on a Spanish salvage operation. He later joined forces with ‘Black’ Sam Bellamy who would ultimately double cross him and steal all his gold…

Meanwhile, Jennings’ arch enemy, Benjamin Hornigold (Blackbeard’s mentor) started up a little club of his own, “The Flying Gang” – a rag tag group of total badasses that would go on to number more than 200 by 1716. After betraying Jennings, Bellamy also signed up just to piss him off.

Then on the 5th of September, 1717, King George (the First) sent out a proclamation and everything changed.

In an attempt to curb the growing threat of piracy against England, King George offered a full pardon to any pirates who turned themselves in and turned away from the pirate life for good. It was a limited time offer (while supplies last, at participating locations, no refunds), after which any pirates who remained outside the law would be hunted to the ends of the Earth and beyond. Nassau (the capitol of piracy) almost unanimously accepted the King’s pardon as hundreds renounced piracy. The ones who didn’t, became dead men walking.

These are their stories…

Pirates from


Black Bart

In 1719, Bartholomew Roberts was a British sailor, newly promoted to Second Mate, aboard the Princess of London when the ship was attacked by… you guessed it: Pirates! Howell Davis and his pirate gang were looking to fill their recruitment quotas, but Roberts was not even remotely interested. But given the choice between tuna chum and ship’s navigator, he chose the latter with a half-assed ‘Shiver me timbers’.

Although becoming a pirate wasn’t exactly on his to do list, he decided if he was going to be a pirate, he was going to be the best goddamn pirate the world had ever seen. Roberts quickly fit in with his cold demeanor, Hulk-like temper, and lack of empathy, but most of all he didn’t take shit from anyone. So six weeks in, when their idiot Captain got himself shot attempting to kidnap the governor of Portugal, no one was surprised when Roberts took his place at the wheel.

Bart’s first order as Captain: VENGEANCE!

meme (baby with fist) - REVENGE - shall be mine!The cut throat pirates came out of nowhere muskets blazing, slicing and dicing their way through the fort, dumping the cannons over the fort walls and setting the town ablaze. After ransacking the island, on their way out of the harbor, just for the hell of it, Roberts used some Portuguese trading vessels for target practice.

Black Bart's boatRoberts was a strict Captain and even laid out some ground rules, which included: No brawling on the ship (only formal duels to the death on shore leave), no stealing (from each other that is), and no drinking after 8pm. I guess you could say – he ran a tight ship…

In his three years as a pirate from 1719 to 1722, Roberts captured and looted over 400 ships from Brazil to the coast of Africa!

Roberts went out in a blaze of glory when his frigate, The Royal Fortune, was outgunned by The Swallow, a top of the line British Man of War. During the gun fight, Black Bart took a cannon blast of grape shot to the neck. His crew gave him an impromptu burial at sea, before hoisting a white flag in surrender. They knew they were screwed without Black Bart Roberts at the helm.

The Dread Pirate Roberts -

“Have you ever considered piracy?” – The Dread Pirate Roberts


Stede Bonnet

Stede Bonnet is fairly unique among pirates in that he was already a wealthy plantation owner in Barbados when he randomly turned to piracy, on a whim. Some say he went crazy or had a mid life crisis, others say his nagging wife led him to a life of crime.

Where most pirates began their career by capturing a vessel, Bonnet started his criminal career by legally financing his own ship, which he dubbed ‘The Revenge’, just because it sounded cool and… well, piratey. So in 1717, Bonnet (who had no previous maritime experience) gathered up a crew (which he paid in wages rather than plunder) and sailed off on his custom-made sloop in search of adventure.

seems legit

Unlike the reluctant Black Bart, Stede was pretty gung ho from the get go, but lacked a suitable resume for a career in piracy, but it’s said he had quite the fashion sense, so I guess he had that going for him. So Bonnet began his pirate career, with no knowledge of sea faring, by sailing up to the Chesapeake Bay (in style) where he somehow managed to capture / plunder four vessels off the coast of Virginia… or at least his experienced crew did. The really odd thing about his method of piracy was that when he plundered a vessel of its goods, he’d pay its crew for their troubles and drop them off at the nearest island.

After making a name for himself in the Carolinas, the well dressed ‘Gentleman Pirate’ immediately ran into some trouble with a Spanish Man-O-War. His first encounter with a fully armed ship went the way of the Kobayashi Maru. They barely made it out alive and probably looked as though they’d had a fight with a Kraken and lost.

After this rather unfortunate encounter, Bonnet and his restless crew limped south to Nassau to lay low from the heat while they made repairs to their severely damaged ship. It was there in the Bahamas that Stede Bonnet met a man by the name of Edward Teach, a man better known in international waters as his rather notorious nick name: Black Beard!

Black Beard quote:

Yes… THAT Black Beard…

Black Beard took one look at Bonnet’s ship, sized up its owner, and walked over to introduce himself. Needless to say, Bonnet was quite the fan boy. Seeing as he was still recovering from his injuries, when Mr. Beard asked if he’d like to team up, Bonnet couldn’t refuse the opportunity to sail alongside his hero. Besides, you don’t really say no to Black Beard.

Pirate buddies


Together, Blackbeard and his new pal made a fortune in the West Indies. What Stede didn’t count on was Blackbeard practically stealing his crew, supplies, and ship from under him. Bonnet soon realized he was essentially a captive on Blackbeard’s flag ship, while one of Beard’s first mates commanded ‘the Revenge’. When they got word of the King’s pardon, Bonnet decided to go straight and become a legitimate privateer. Blackbeard tricked him into thinking he too was seeking royal amnesty.

When Bonnet returned to the inlet where they had anchored, Blackbeard was gone without a trace… and so was his loot. The Revenge had been stripped bare and he found two dozen crew members stranded on a nearby island, abandoned by Blackbeard. The marooned men were more than happy to join Bonnet’s company and were on board with his plans to go straight.

Stede Bonnet took on the alias of Captain Thomas, refit his ship, changed its name to the Royal James and set sail for the New England coast. On the way he and his crew ransacked multiple ships for food and supplies, but each time Bonnet – er, I mean “Thomas”, traded them random items for their stolen goods and sometimes even outright paid for them, saying he was sorry as he pillaged their cargo.

Black Beards Party

Black Beard’s parrrrrty… Spring Break 1718

En route, their ship came alongside another vessel selling cider. The drunk men aboard told them that Blackbeard was throwing a massive kegger at Ocracoke Inlet. Bonnet was furious he wasn’t invited.

Still pissed about his bro stealing his doe, Bonnet changed his mind about going legit and altered course to have a word with Blackbeard. After four days of searching for Blackbeard without any luck, Bonnet and his crew encountered a sloop full of liquor off Cape Henry. He sent 8 guys over, presumably to get directions to Blackbeard’s next pirate party. Much to his dismay, his men abandoned him to join the other crew and sailed off with all their rum.

At this point, Bonnet was pissed. He basically went postal and began attacking every single ship he came across.

Mail Man:

So much for a clean record.

Then in July of 1718, ‘The Royal James’ docked at Cape Fear for repairs… for two months… It was around this time that the infamous Charles Vane threatened the colony’s governor. In response, Colonel William Rhett dispatched two ships: The Henry and The Sea Nymph to take care of Vane, but he escaped. Then word inevitably reached Rhett that there was another pirate ship in the harbor… The Colonel turned his attention to ‘The Royal James’.

On the morning of September 26, 1718, Bonnet attempted to make a run for it, but as Murphy’s Law would have it, his ship ran aground in the shallow water. A battle ensued that lasted for hours. Between the cannon fire and shit talking, Rhett’s ships also ran aground.

Pirate battle

Eventually the Colonel gained the upper hand and had the pirates surrounded. The trash talking really quieted down at that point and Bonnet surrendered. Much to Colonel Rhett’s surprise, “Captain Thomas” was none other than THE Gentleman Pirate himself, Blackbeard’s “best buddy”.

After pleading his case of misfortune (wrong time, wrong place, etc), Stede Bonnet was tried, convicted as an accomplice of Blackbeard and sentenced to death.

I guess you could say the ‘Pirate Life’ was not for him…

Charlie Brown as a pirate

“Good grief!”


As bad as Stede Bonnet was, William ‘Captain’ Kidd was literally the worst.

'You are without a doubt the worst pirate I've ever heard of.' Jack Sparrow: 'But you have heard of me.' - scene from

William Kidd was not the most successful of pirates nor was he the most feared, in fact he was probably one of the most Epic Fails in the history of piracy. This semi-legendary figure started as a privateer based out of New York, hunting French merchant ships, with little to no success. He was then hired to fend off pirates attacking ships of the East Indian Trading Company, in a creaky old boat that was barely sea worthy. His crew almost mutinied when he chickened out of attacking a Dutch ship, and he killed his gunner, William Moore, for back talking.

Then in 1698, Kidd laid eyes on what he thought was his key to success: The Quedagh Merchant, which he assumed with a name like that, was a French vessel. He was wrong. His first successful raid against another ship turned out to be another English vessel, much to his surprise. As a result, he became a wanted man: public enemy number one.

half buried treasure

No one will ever find it…

Kidd panicked and ditched the captured ship off the island of Hispaniola. He sailed back to New York where he hurriedly buried his stolen treasure on Gardiners Island (the one and only time a pirate actually buried his loot in recorded history), and pleaded his case to the Colonial Governor, the Earl of Bellomont.

Unfortunately his half-buried treasure was easily discovered and used as evidence against him. He was then shipped off to England where he was tried, found guilty, and subsequently hanged at execution dock.

During the proceeding the noose broke twice! The poor sap finally died on the third attempt. Kidd’s body was covered in tar and left out for public display as a warning to other wannabee pirates.

depiction of William Kidd hanging...

Ta be concluded in Part 3 with Black Beard’s Last Stand and more! 

                                                            ERIK SLADER

Hope ya landlubbers enjoyed tis here Pirate Edition of me blog, “Epik Fails of History!” If ye scurvy bilge-rats have any questions, concerns, er suggestions, let yer Cap’n know in the comments below! Alas be sharrr ta ‘Like’ on Facebook, or Follow on Twitter, and smartly SHARE IT with yar mateys! Fair winds me hearties!

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Hook - poster

—– More articles on Historic Failure:








“The Republic of Pirates” by Colin Woodard

“Under the Black Flag: The Romance and the Reality of Life Among Pirates” by David Cordingly

“A General History of the Pyrates” by Daniel Defoe

“Badass” by Ben Thompson

“Assassin’s Creed IV: Black Flag” (PS4 / Xbox One)

“True Caribbean Pirates” – History Channel Documentary (2006)

The Saint Augustine Pirate and Treasure Museum

Erik Slader
Erik Slader
Erik Slader is the creator of “Epik Fails of History” a blog (and podcast) about the most epic fails… of history. With Ben Thompson, Erik is the co-author of the Epic Fails book series. He has a Bachelor’s Degree in Digital Media, once managed a comic book shop, has a weakness for fancy coffee and currently lives in Green Cove Springs, Florida with too many cats.


  1. […] be continued… CLICK HERE for PART 2! – arrr else ya’ll be walkin’ the plank ta Davy Jones’s […]


  3. […] THE GOLDEN AGE OF PIRACY (Part Two) […]

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