Here’s a fun pirate fact for you: If you took the exceptionally-infamous pirates Blackbeard, Anne Bonny, and Edward Low, combined them all into a Power Rangers MegaZord Godzilla of cutlass-swinging mayhem like some kind of murder-riffic All-Star Piracy Dream Team, and heaped their dozens and dozens of captured, plundered, burned, and mutilated enemy ships into one gigantic towering scrap heap inferno of twisted timber and shattered femurs, that super-skyscraper of carnage still wouldn’t even come close to the number of vessels that fell victim to the single most successful pirate to ever sail the seven seas – the infamous Captain Bartholomew Roberts. A booty-snatching terror of the Spanish Main, “Black Bart” was the undisputed king of swashbuckling scurvy cutthroats, a brutal murderer who decorated his ship with the hanged corpses of his mortal enemies, and a hardcore sea-reaver who terrorized merchant shipping and painted the Atlantic Ocean blood-red from Canada to Madagascar.
Between the years 1719 and 1722 – an astoundingly-long career considering that most pirates were lucky to go twelve months without being hanged from the neck until dead, Black Bart and his veritable armada of heavily-armed pirate warships is credited with single-handedly plundering and destroying over four hundred vessels ranging from friendly little merchantmen to badass gunslinging Royal Navy war frigates. He took on Portuguese treasure fleets, attacked Dutch colonies, and even assimilated a vanquished French warship into his pirate fleet. No other crew in European history even comes close to a record like that.
Despite sporting a super sweet, dastardly-sounding nickname like “Black Bart,” Bartholomew Roberts honestly wasn’t what you expect when you think about the most dangerous ball-crushing oceanic marauder to ever hoist a mainsail made out of the flayed skins of his foes. This Welsh gentleman was tall, attractive, good with women, drank a nice warm cup of English breakfast tea every morning, and enjoying walking the deck wearing an expensive red silk coat and a super fancy hat that was so awesome that several contemporary sources make a specific point of talking about how fucking dapper it looked. Even his nickname, Black Bart, is believed to have come from his dark, swarthy complexion rather than his murderous tendencies and unquenchable desire for endless vengeance and plunder.
Hell, Black Bart didn’t even really wanna be a pirate in the first place. This hard-working guy originally tried to be a legitimate sailor, working as Second Mate on a slave ship called the Princess of London that operated out of West Africa. When his ship was overtaken and captured off the coast of Ghana by the already-infamous dread pirate Howell Davis in 1719, Bartholomew Roberts gave everyone the finger and refused to join the pirate crew despite their none-too-polite invitation. It was only really when some dude with a hook for a hand threatened to cut Roberts’ balls off and use them to chum the waters for Great Whites that Roberts changed his mind and decided to join Davis’s pirate crew as a navigator.
Roberts’ skill at running a ship, experience as a formerly-legit nautical officer, and red-hot temper that exploded with the fury of a thousand gallons of liquid-hot magma quickly earned him a place of respect among his newfound pirate friends, and thanks in part to Roberts’ sailing chops the crew was able to launch a successful attack on a Dutch merchant ship that just so happened to be carrying the goddamn Governor of Accra and his personal cache of 15,000 pounds worth of silver coinage. It would be one of the biggest hauls in the history of European piracy, and Roberts had only been on the job for like a week and a half.
Not long after that, Captain Davis got the brilliant idea to start shit with the Portuguese island of Principe, a small port just off the southern coast of Nigeria, and it didn’t work out all that well for him. Davis put on a disguise, sailed into shore, and walked right up to the island’s Governor, pretending to be a pirate hunter looking for Portuguese help. Davis’ plan was to trick the Governor into coming aboard his ship, capture him, and hold him for a huge ransom, but some asshole tipped the Governor off about the plan and instead of pulling off a sweet kidnapping/extortion plot Captain Davis was unceremoniously gunned down by Portuguese infantry right in the middle of the Governor’s Palace.
Black Bart had been a pirate for a mere six weeks. He was already so popular with his men that they voted him in to replace Davis as Captain.
Captain Bartholomew Roberts’ first official order was to avenge Captain Davis’ death. Charles Bronson style.
Screaming into battle with two flintlock pistols and a terrifying-looking cutlass Black Bart led his men storming into town, destroyed the garrison, threw all the fort’s cannons into the ocean, shelled the town with a couple broadsides of raking cannon fire, and set three Portuguese trading ships ablaze in the harbor on his way out of town. From that point on, Black Bart Roberts was officially at war with every single person on Earth – including, at times, members of his own crew.
Roberts set sail from Africa, crossed the Atlantic Ocean, and started wrecking shit in South America. Off the coast of Brazil, he caught a super lucky break and just so happened to run into the Portuguese Treasure Fleet – 42 ships filled to the brim with gold and silver from the New World. Unwilling to take his 26-gun vessel against the two massive 70-gun Portuguese warships that were escorting the fleet, Roberts instead hatched an awesomely-diabolical plan. First, he ran a Portuguese flag up his mast, fell into formation with the fleet, and sailed up to the smallest little ship he could find. He got real close like he was just going to say what’s up, but then at the last second he and his pirates jumped onto their ship and threatened to kill everyone aboard if they didn’t tell him which vessel in the treasure fleet had the most loot to plunder. Once those dudes pointed out the main treasure ship, Black Bart sailed right up to it – in broad fucking daylight because he had ridiculously gigantic Black Bart gonads – boarded the thing at the head of a swarming mass of fucking cutthroat pirates, captured it without firing a shot, looted 90,000 gold coins from the ship’s hold, and then peeled the fuck outta there before the two hulking battleships could get close enough to fire on him. Besides the crap-ton of gold, the crown jewel of the haul was a fucking fist-sized blood diamond hand-cut as a present for the King of Portugal that was probably worth more cash than you’ll make in your entire life. Because he was the big pimpin’ style of pirate, Roberts naturally wore this priceless hunk of gemstone on a chain around his neck for the rest of his life.
Not long after this epic haul, some of Roberts’ crew mutinied and tried to make off with a big portion of his hard-plundered gold. So, in order to keep his men in line moving forward, Black Bart set up a well-defined series of Pirate Rules that still survive to this day. He promised that every man on the crew was guaranteed to have a vote on important subjects and an equal share of the loot, but also said that there would be no women or gambling on the ship, no drinking below decks after eight PM, and if you wanted to fight a fellow crew member to the death you had to do it on land and not on the ship. Roberts, naturally, didn’t always adhere to these rules himself – one time a crew member was pissing him off so he ran the guy through with his sword right then and there. When another crew member mentioned that hey, you know, this kind of goes against your Pirate Rules, Roberts ran that guy through as well. In case you’re curious how badass pirates can be, that second guy responded to being impaled by punching Roberts in the face. Roberts, infuriated that the man would strike a superior officer, ordered the already-stabbed man be flogged in front of the entire crew.
Oh, and as another semi-hilarious side note, if you were an Irishman you didn’t count as a crew member. This is because the guy in charge of the mutiny had been Irish, and nobody on earth could hold a grudge like Bartholomew Roberts.
One of four Jolly Rogers used
by Black Bart Roberts.
Roberts plundered South America and the Caribbean for a while, but eventually headed up to Newfoundland in 1720 after the governors of Barbados and Martinique hired a bunch of asshole pirate-hunters to try and murder him. In Newfoundland, a freezing-cold portion of Canada that really probably wasn’t expecting to be on the receiving end of a fucking pirate raid, Bartholomew Roberts attacked and destroyed something like 30 or 40 ships ranging from fishing boats to French warships. In Trepassy Harbor alone Black Bart sunk and burned 22 ships while they were anchored in port, mostly just to be a dick.
Throughout the rest of 1720, Roberts headed back and laid waste to the Caribbean. Calling himself “The Admiral of the Leeward Islands,” Black Bart commanded four ships and over 500 men in an epic rain of carnage and destruction that left dozens of ships and the port city of St. Kitts in smoldering ruins. From the deck of his flagship Royal Fortune, a 42-gun frigate believed to be the biggest and most well-armed pirate ship in Caribbean history, Roberts wrought havoc on merchant shipping across the New World. He burned 20 ships in Martinique Harbor, captured a brigantine that happened to have the Governor of Martinique on board, and then hung the governor from the yardarm of Royal Fortune. To really drive home that point about holding grudges, Roberts spent the next couple months sailing around with the governor’s dead body suspended above his ship’s deck as a warning to others.
The Dread Pirate Roberts takes
When things got a little too hot Black Bart sailed back across the Atlantic again (no small task in the early 18th century), and went back to work destroying ships off the coast of Senegal, burning and looting with impunity.
Eventually, however, luck caught up with Black Bart. On one rainy, windy morning in February 1722, Black Bart looked through his spyglass and saw the approaching sails of HMS Swallow – a British ship-of-the-line that was a little bigger and better-armed than Royal Fortune. Even though Bart probably had plenty of time to escape with his life, the pirate captain instead flashed his nuts once again, woke up his hungover-or-possibly-still-drunk-from-last-night crew, and ordered them to man their guns and go toe-to-toe with a Royal Navy warship in the battle of their lives.
The Swallow closed in on the Royal Fortune, appearing through the mist, rain, and wind, and quickly pulling even with the notorious pirate vessel. Both ships turned and unleashed devastating broadsides simultaneously, ripping apart the air with the sound of over forty cannons belching out grapeshot, cannonballs, and other horrible things.
No sooner had the smoke cleared than Captain Bartholomew Roberts slumped over the gunwale of the ship, his throat torn in a blaze of glory out by a screaming burst of jagged grapeshot pellets. His men dumped the 40-year-old Captain over the edge into the ocean, following a standing order not to let the enemy capture his body. They surrendered Royal Fortune shortly after, and the British Crown ensured that every man in the crew was executed by hanging.
The last of the great pirates – and by far the most successful – was no more.
Cordingly, David. Under the Black Flag. Random House, 2013.
Farman, John. The Short and Bloody History of Pirates. Millbrook, 2002.
Johnson, Charles. A General History of the Most Notorious Pyrates. Books on Demand, 2009.
Little, Benerson. How History's Greatest Pirates Pillaged, Plundered, and Got Away With It. Fair Winds, 2010.