The Day the Wickedest Pirate City Sank Beneath the SeaPort Royal sinks, the Dutchman rises, and the richest rogues reveal their golden secrets. Issue #7 – June 6th, 2025

Ahoy, Matey

The sea’s whisperin’ dark tales this week, matey—of cursed cities, ghost ships, and gold-laden plunder.Fill yer cup, grip yer cutlass—adventure’s knockin’ like a cannon blast at midnight.

⚓ This Week in Pirate History

⚓ June 7, 1692 – The Wickedest City Sinks Beneath the Waves

At exactly 11:43 AM on a sunny June morning, the earth beneath Port Royal, Jamaica—the very heart of Caribbean piracy—began to heave and crack. In mere moments, the “wickedest city in the world” became a watery grave.

Once the crown jewel of piracy, Port Royal was known as the “storehouse and treasury of the West Indies,” a den of debauchery where pirates, privateers, and profiteers ruled the rum-soaked streets. But on June 7, 1692, the city paid the ultimate price for its sins.

A massive earthquake struck, followed swiftly by a towering tsunami that swallowed buildings whole and dragged ships from their moorings. Streets split apart. Entire wharves plunged into the sea. A pocket watch, discovered in 1959 by underwater archaeologists, stopped forever at the exact moment the city fell: 11:43 AM.

Nearly 2,000 souls perished in the disaster, and another 3,000 died in the days that followed from wounds and disease. Half the city disappeared beneath the waves, including the infamous dens of vice and taverns where pirates once toasted their bloody victories.

Today, the sunken ruins of Port Royal lie preserved under the sea—a ghostly Atlantis of the pirate age, where time stands still and the sins of the past linger just below the surface.

⚓ Legacy: Port Royal was swallowed by the sea, but its legend endures—a stark reminder that the wages of wickedness may be paid in saltwater and sorrow.

Read more about Port Royal’s watery fate →

🪙 The Five Richest Pirates from 1650–1725

These rogues didn’t just sail the seas—they owned ‘em! From the Caribbean to the Indian Ocean, these black-hearted buccaneers carved their names into legend with fortunes that’d make a king green with envy. Here be their haul in today’s money:

🪙 5. Black Bart Roberts – 32 MillionA Welsh devil with a dashing smile and a cutlass sharper than a governor’s tongue, Bartholomew Roberts—better known as Black Bart—took over 400 ships in his day. They say he wrote the first Pirate Code, the very laws that kept pirate crews from killin’ each other on sight. His nickname, “The Dread Pirate Roberts,” echoes to this day—aye, even in The Princess Bride.

🪙 4. John Bowen – 40 Million“Johnny Boy” Bowen was a Creole pirate with a lucky streak longer than a sea serpent. Captured by French pirates, he turned coat and became a pirate himself—sailin’ for just four years, yet plunderin’ enough to fill a dozen treasure chests. He made it back to Madagascar to enjoy his spoils... but poor Johnny only lived six months into retirement before dyin’ of a cursed gut illness.

🪙 3. Thomas Tew – 103 MillionA true pioneer, Thomas Tew charted the infamous “Pirate Round”—a route round the Cape of Good Hope to the riches of the Indian Ocean. His bold raids made him a legend, and other pirates followed his wake for years. Alas, Tew met his end in battle at the age of 46, and most of his loot never touched dry land.

🪙 2. Sir Francis Drake – 115 MillionThe Spaniards called him El Draque, and with good reason—Sir Francis Drake was the first pirate to circumnavigate the globe, leaving a trail of plunder and burnt Spanish ships in his wake. The Spanish Crown hated him so much they put a million-dollar bounty on his head. He out-sailed whole armadas and built a fortune fit for a king.

🪙 1. Black Sam Bellamy – 120 MillionBarely a year in the Caribbean, yet Black Sam Bellamy pulled off one of the richest scores in pirate history—the capture of the Whydah Gally, laden with five tons of treasure. But fate be a cruel mistress: Bellamy and his crew sank off the coast of New England, takin’ their golden haul to Davy Jones’ Locker. He died young, tryin’ to reunite with his one true love ashore.

⚓ Legacy: Riches, fame, and tragedy—all in a pirate’s life. These men lived fast, plundered hard, and left behind tales that still echo across the seven seas.

Read more on Pirate Lore →

⚓ Tales from the Depths – The Legend of the Flying Dutchman

She’s the most infamous ghost ship to ever haunt the seas—a spectral vessel cursed to sail the oceans for all eternity, unable to make port, her tattered sails billowin’ in storms that’d sink any mortal ship.

This be the tale of the Flying Dutchman.

The legend first set sail in the 17th century, born in the Golden Age of Dutch maritime power. Tales tell of a captain—often named Hendrik van der Decken—who swore to round the Cape of Good Hope during a brutal storm, defying the wrath of the seas and perhaps even the Almighty himself. For his arrogance, he and his crew were cursed to sail forevermore, their ship doomed to wander the oceans as a ghostly omen of bad luck.

The legend of the Flying Dutchman has been told and retold in many forms:

• Richard Wagner’s opera cast her tale in music and myth.

• The Pirates of the Caribbean films wove her into the story of Davy Jones and his cursed crew.

• And in art, song, and lore, the Dutchman sails on, forever cursed, forever feared.

⚓ Legacy: The Flying Dutchman is a symbol of hubris, doom, and the price of defying the gods—a tale every sailor whispers and every pirate secretly fears.

🏴‍☠️ Plunder Pick o’ the Week

⚓ JM Bricklayer Flying Dutchman Pirate Ship – A Ghostly Build for Bold Buccaneers

Relive legendary tales and sail the enigmatic pirate seas with this stunning Flying Dutchman building set by JM Bricklayer.

With over 1,000 ghostly pieces, ye can recreate the fabled ship that can never dock, its phantom sails forever cursed to wander the waves. Whether ye be a modelin’ enthusiast or a pirate aficionado, this build be a treasure for yer shelf and a bold challenge for yer hands.

Craft the legendary ghost ship, feel the mist of the high seas in yer bones, and know that with every brick, ye’re relivin’ a tale whispered across the ages.

🛒 Snag yer Flying Dutchman here →

🏴‍☠️ Upcoming Events for Scallywags & Salty Dogs

📍 Put-in-Bay Pyrate Fest XVII – Ohio

📅 June 27–29, 2025A weekend of island mayhem with pirate skits, battles, treasure hunts, and grog aplenty.Event Link →

📍 Kingston Pirate Festival – Mike Wallace Park, Kingston WA

📅 July 5–6, 2025Family-friendly pirate fun with live music, kids’ activities, pirate vendors, and plenty o’ swagger.Event Link →

🗣️ Share the Spoils, Matey!

Know a landlubber who’d love tales of treasure, ghost ships, and real pirate history? Don’t keep the gold to yerself—send ‘em our way!

📜 Sign up here → https://www.piratefanclub.com/weeklynewsletter-thepiraterepublic

Fair winds and full inboxes!

Sail with us across the digital seas:📜 TikTok: @thepiraterepublic▶️ YouTube: The Pirate Republic

🎖️ Thanks for Embarkin’ on the Voyage

We set sail every Friday, storm or shine. Keep yer spyglass pointed at the horizon...and may yer week be full o’ plunder, parlay, and just the right amount o’ mutiny.

Share this letter with yer crewmates, an if ye find treasure or tales worth tell’n, send them to captainblackquill@gmail.com.

 Disclosure: Some links in this newsletter are affiliate links, which means we may earn doubloons (aka a small commission) if you make a purchase—at no extra cost to you. Thanks for supporting The Pirate Republic, ya savvy sea dog!