Bartholomew “Black Bart” Roberts
(1682–1722)
Welsh Pirate Captain
& Atlantic Privateer-Terror
“A man can’t die but once—so he may as well make the bastards remember it.”
— attributed to Bartholomew Roberts, probably after too much rum and too little patience
THE ELEGANT MENACE
Bartholomew “Black Bart” Roberts did not enter history. He violated it. He kicked the Atlantic wide open, shook out its pockets, and asked it politely to scream louder. Picture smoke—thick, oily, and drifting low like it’s trying to escape the gunfire. Cannon blasts strobe the air. Men shriek. Timber groans. And above it all, snapping in the wind like a funeral banner, flies his black flag: a skeleton toasting death.
Roberts stands at the rail of the Royal Fortune, powdered wig perfectly arranged despite the carnage. Gold-trimmed coat, crimson waistcoat, sword hanging with aristocratic arrogance. He looks less like a pirate and more like a man about to sue someone for scuffing his shoes. Then he turns to his gunners and says something dry enough to desiccate a coconut.
“Let’s finish this before the tea cools.”
And then he earns his legend.
ORIGIN OF A MONSTER (1682–1719)
Our man began life far less glamorously—as plain John Roberts of Pembrokeshire, Wales. A quiet, competent sailor. The kind of guy who would’ve spent forty years tying knots, avoiding scurvy, and complaining about biscuit quality.
He wasn’t ambitious. He wasn’t violent. He certainly wasn’t “king of all pirates” material.
But the sea is hilarious like that.
In 1719, the merchant ship Princess—Roberts aboard—was taken by Howell Davis, a pirate captain with charm, wit, and the general life expectancy of a firecracker. Davis noticed Roberts seemed unusually competent (and not drunk), so he drafted him on the spot.
Roberts protested. Davis insisted. The pirate retirement plan was “you’re dead,” so Roberts accepted.
Minutes into his new job, he realized something shocking:
He liked it.
Pirate life offered… democracy. Equality. Voting. Shares. A complete rejection of the rigid class ladder that normally kept Welsh sailors at the mop end of history. Roberts began thinking dangerous thoughts—about freedom, respect, and not being bossed around by men who couldn’t navigate sober.
Then Davis got himself killed in an ambush—classic pirate HR problem. The crew needed a new captain.
They chose Roberts.
Not because he wanted it. Because he was smart, calm, and unlikely to start pointless fights with other pirates. That, plus nobody else wanted the workload.
And with that, a bookish Welsh sailor became the most lethal marauder the Atlantic would ever meet.
THE RISE OF BLACK BART: PIRATE CEO
Roberts approached piracy with the efficiency of a tax auditor and the ambition of a man who decides that if he’s going to be damned, he’s going to be spectacularly damned.
Within weeks he:
Raided a harbor of 42 Portuguese ships like he was shopping for a new carriage
Stole enough gold and jewels to embarrass several nobles
Pioneered streamlined attack methods
Standardized crew discipline
Enforced dress codes so strict he basically invented “pirate business casual”
Not bad for a guy who’d been a pirate for the same amount of time it takes to grow a disappointing mustache.
Roberts fought like a strategist, not a berserker. His ships were fast, sleek, terrifyingly well-run. He didn’t drink heavily. He didn’t tolerate incompetence. He kept order with iron rules and sarcastic comments sharp enough to cut rope.
And he had style—dangerous style.
Silk clothes. Plumed hat. A ruby-handled sword. Enough jewelry to blind a magpie. He looked like a nobleman possessed by a demon with expensive taste.
The Atlantic took notice.
HIS GOLDEN YEAR OF ABSOLUTE PIRATE NONSENSE
The year 1720 alone would’ve been a career for any other pirate. For Roberts, it was a warm-up stretch.
He blockaded whole coasts.
He captured so many ships that logbooks had to use extra pages.
He attacked naval escorts like they were mildly inconvenient seagulls.
He once forced a convoy of British merchantmen to line up for inspection—like schoolboys before a headmaster—while he walked the decks and selected the best prizes. The rest he released with a polite note instructing them to stop sailing so pathetically.
He had the nerve of a man who believed the universe owed him a refund.
Roberts even collected his own personal grievances list: any governor, navy officer, or colonial bureaucrat who annoyed him earned a red mark. He then made it a hobby to burn their ships, plunder their towns, or humiliate them in some public, unforgettable way.
He wasn’t just a pirate.
He was a customer-service complaint personified.
THE BLACK FLAG OF BART ROBERTS
Roberts understood branding before Instagram made it cheap.
His flags were works of psychological warfare:
One showed himself standing on two skulls labeled ABH and AMH — “A Barbadian’s Head” and “A Martinican’s Head.”
Another depicted Death holding an hourglass while toasting him with a goblet—as if the Grim Reaper were his drinking buddy.
He didn’t just scare people.
He marketed fear.
THE DOWNFALL: A CANNONBALL WITH GREAT COMEDIC TIMING
By 1722, Roberts had captured 400 ships—more than any pirate in history. The British finally stopped pretending the problem would go away if they wrote enough letters, and sent Captain Chaloner Ogle with a warship, the Swallow, to end the Black Bart situation.
Roberts knew they were coming.
He’d beaten navies before.
He felt untouchable.
But even legends get one bad morning.
Roberts had just finished inspecting a potential target when Ogle’s ship appeared on the horizon. Roberts—ever the aristocratic showman—dressed in his finest red waistcoat and hat. If he was going to fight a warship, he’d at least look fabulous doing it.
The battle began with maneuvering and cannon fire…but Roberts never made it to the exciting part.
A single chain shot—two iron balls linked by a bar—flew across the deck and hit him square in the throat. His head didn’t come clean off, but the effect was… decisive. He collapsed instantly.
The crew, shocked, fulfilled his final wish: throw my body overboard so the British can’t hang it.
So the most successful pirate in Atlantic history sank beneath the waves like a stone dressed for a royal wedding.
The Swallow captured the rest, hanged most of them, and declared the golden age of piracy officially dead.
But Roberts?
Roberts slipped the noose.
Even in death, he refused to be properly inconvenienced.
MYTH, MEMORY & MISCHIEF
History has a habit of polishing monsters into heroes or sanding saints down into sinners. Roberts got the hero treatment—but not the kind you’d expect.
Modern portrayals make him look glamorous, principled, and stylishly doomed. That last part is accurate. But the truth is worse and better: he was a brilliant, ruthless, deeply sarcastic man who mixed Enlightenment-era governance with high-seas mayhem.
He inspired songs, paintings, tall tales, and a long-running argument among historians about whether he was a psychopath, a visionary, or simply a Welshman with too much free time.
Pop culture trimmed the rough edges. They kept the coat, ditched the mass robbery, and forgot the part where he accidentally reinvented corporate management on a pirate ship.
Some say he was the model for every fictional pirate captain with flair. Others say he was the last truly competent man to ever command a ship while wearing jewelry worth a mid-sized town.
Either way, he lives on—not because he looted the Atlantic, but because he embarrassed the British Navy so thoroughly they had to rewrite whole sections of maritime law just to cope.
That’s legacy.
warrior rank #178
In the end, Bartholomew Roberts proved one eternal truth: if you must die, do it dressed to kill—and leave the ocean laughing.
SOURCES
Angus Konstam, Black Bart Roberts: The Greatest Pirate of Them All
David Cordingly, Under the Black Flag
Colin Woodard, The Republic of Pirates
Marcus Rediker, Villains of All Nations
Robert’s Quarterly Guide to Workplace Efficiency and Unscheduled Murder, 1721 (lost at sea, probably for the best)
The Atlantic’s Worst Dressed List, 1720 (Roberts removed for overdressing)
