The Pirate Republic - Halloween on the High Seas – The Flying Dutchman Rises!
- Captain Blackquill
- 5 days ago
- 5 min read
On Halloween night, the legends come alive — if ye dare to read them. Issue #28 –Oct 31st, 2025
Ahoy, Matey
It’s Halloween on the high seas, me hearties —
when the veil between the living and the damned grows thin, and the ghosts of the ocean rise to tell their tales.
Tonight, we sail through haunted waters: Blackbeard dumps his cocoa to spite the world, Bartholomew Roberts conquers fifteen ships in three days, and the Flying Dutchman returns from the mist to claim lost souls once more.
So trim the lanterns, pour a shot o’ rum, and read by candlelight — for on this night, even the bravest sailor listens for the creak of phantom sails.
⚓ This Week in Pirate History
Oct 30, 1717 – Blackbeard’s Cocoa Raid
As the year turned toward winter, Edward Thatch — “Blackbeard” — seized a merchant sloop bound for New York from Curaçao, commanded by Captain Goelet. The cargo hold brimmed with cocoa, a valuable colonial treasure.
But Blackbeard, ever the unpredictable devil, had no interest in sweets. He dumped the entire cargo overboard, watching the floating beans stain the sea like spilled blood. Then, with the calm calculation of a man rearranging furniture, he transferred all supplies and arms from one of his own sloops onto the captured vessel — a sleeker, faster prize.
When the work was done, Thatch did something few pirates would ever consider mercy: he handed his old sloop, the Sea Nymph, over to Captain Goelet and allowed him to sail home to New York.
The gesture wasn’t born of kindness. It was theater — a display of power from a man who could give and take fortune at will. Blackbeard needed no prisoners, only legend. And legend, that day, he earned again.
1721 – Bartholomew Roberts Captures 15 Ships in 3 Days
In the tropical waters off St. Lucia, the infamous Bartholomew “Black Bart” Roberts unleashed a storm of piracy so fierce that even seasoned captains whispered his name with dread.
Over the course of just three days, Roberts and his black-flagged fleet captured fifteen ships, one after another, like a hawk picking prey from a flock. Merchantmen, sloops, and coastal traders — none escaped the Welshman’s precision and ferocity.
Roberts was no drunken brute; he was a strategist of the sea. Known for his discipline and boldness, he turned piracy into a kind of deadly art. At his height, Roberts commanded more than 400 men and a flotilla of war-ready ships, taking over 470 prizes in just three years — more than any other pirate of the Golden Age.
He dressed like a nobleman in crimson and lace, sipped wine from stolen crystal, and demanded that his crew maintain order aboard even while waging chaos upon the waves.
It was said that when his sails appeared on the horizon, entire convoys struck their colors without a shot fired. For in the age of pirates, none were as feared — nor as successful — as Bartholomew Roberts.
🎃 Haunted Seas of October and a ghostly legend that continues to haunt sailor’s dreams to this day.
The Curse of the Flying Dutchman
There are whispers among sailors that somewhere beyond the horizon sails a ship that no man can hail and no storm can sink — the Flying Dutchman, the ghost of the sea herself.
They say she first appeared off the Cape of Good Hope, where a Dutch captain, Willem van der Decken, defied heaven’s wrath and swore he would round the cape “if it took till Judgment Day.” The wind answered with fury. His crew begged him to turn back, but the captain cursed God and drove the ship straight into the black heart of the storm.
Lightning split the sky — and when it cleared, the ship was gone. All hands lost. Or so it seemed.
From that night onward, sailors began to see her: a phantom galleon with tattered gray sails that never fill with wind, lanterns glowing an unholy green, and a captain standing motionless at the helm, his eyes like dead stars. Those who cross her path are doomed — the sea itself claims them within the year.
Witnesses swear the Dutchman brings bad omens: ships run aground on clear nights, crews vanish without a sound, and messages in bottles drift ashore marked only with a single word — “Condemned.”
And so the old superstition endures:If the mist thickens suddenly, and the air grows cold though no storm is near — keep your heading and do not look astern. For if ye see her, the Flying Dutchman will follow until your ship joins her eternal voyage through the damned seas.
“No compass points where she sails. No soul returns who boards her.”
💰 Plunder Pick of the Week
Museum-Quality Flying Dutchman Ship Model
Dare ye bring the legend home? This museum-quality Flying Dutchman model captures the dread beauty of the world’s most infamous ghost ship.
Painstakingly handcrafted from wood, this 60-inch fully assembled masterpiece features ghostly sails, weathered timbers, and the eerie presence of something long dead but not forgotten. Each detail evokes the cursed grandeur of the Dutchman herself — a perfect showpiece for collectors and sea-dogs with a taste for the macabre.
While she’s currently out of stock (perhaps lost again in the mists), this phantom vessel is worth the gaze of any soul who dares. Should she return, best claim her before the curse does.
But be warned — stare too long into her ghostly hull, and ye might just hear a whisper on the wind calling ye by name.
🏴☠️ Joke to Tell the Cabin Boy on Halloween
Q: Why did the ghost pirate quit his crew?A: He couldn’t handle the booooo-ty! 👻💰
🎪 Festival Forecast
🏴☠️ Pirate Weekend at the Louisiana Renaissance Festival – Hammond, LA (Nov 8–9, 2025)
The village of Albright transforms into a pirate haven during Pirate Weekend, part of the grand Louisiana Renaissance Festival. Pirates, privateers, and swashbucklers take over the streets for two glorious days of rum-soaked revelry.
Expect:
Pirate encampments, costume contests, and lively duels ⚔️
Sea shanties, tavern singalongs, and artisan markets
Merriment, mischief, and more grog than sense
If ye can make port in Hammond, Louisiana, this is one festival worth the voyage.
☠️ Captain’s Log
As October fades, the sea grows quieter — but never still. From Blackbeard’s cocoa raid to Bartholomew Roberts’ reign, and the cursed legend of the Flying Dutchman, this month proved that even centuries later, pirates still haunt the tides.
So keep yer wits sharp, yer rum close, and yer compass true — for though the ghosts may rest, their stories never sleep.
Fair winds and haunted waters,– Captain Blackquill
🗣️ Share the Spoils, Matey!
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Fair winds and full inboxes!
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🎖️ 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.
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