History is full of incredible people whose lives often overshadow fictional characters. From pirates to eccentric dukes, their journeys are packed with drama, love, and unbelievable twists worthy of the silver screen.
“Lord” Timothy Dexter
Sometimes, luck trumps intelligence, and no one embodies this more than Timothy Dexter, an 18th-century Massachusetts businessman. Born into a working-class family with little education, Dexter yearned for high society. He married a wealthy widow while working as a leather craftsman apprentice, setting him on the path to riches.
Dexter’s biggest break came after the Revolutionary War. Continental currency had plummeted in value, leading wealthy Americans to buy it from struggling soldiers as a sign of goodwill. Dexter invested his entire fortune in Continental dollars. When Alexander Hamilton implemented his financial plan, Dexter traded his Continentals for treasury bonds, amassing a considerable fortune.
Legend says Dexter made bizarre yet profitable financial decisions. One tale claims he exported wool mittens to the tropical Indies, where merchants bought them for Siberia. Another time, he supposedly shipped coal to Newcastle during a miners’ strike, selling his cargo at a premium.
Yearning to display his intellect, Lord Dexter (as he called himself) wrote a 9,000-word book filled with eccentricities like random capitalization, spelling errors, and no punctuation. The title? A Pickle for the Knowing Ones or Plain Truth in a Homespun Dress.
Howard Blackburn
Howard Blackburn, a fisherman from Nova Scotia and Massachusetts, became a local hero in 1883 at just 24 years old. A winter storm blew his schooner off course, forcing him to row back in frigid conditions without mittens. To keep rowing, Blackburn kept his hands curved, even as they froze. After five days without food, water, or sleep, he returned, though his mate died, and Blackburn lost all his fingers and a toe.
Blackburn’s fishing career ended, but his bravery earned him fame. He opened a tavern, which still stands today. In 1899, he returned to the sea, solo-crossing the Atlantic (his first of two) aboard the Great Western in 62 days. While others had done this before, they still had the use of their fingers. Even at 72, Blackburn planned another transatlantic voyage.
Henry Every
Henry Every, known as the “King of Pirates,” rivaled even the most famous buccaneers. In 1695, he executed one of the greatest plunders in pirate history.
Every learned of a Mughal Empire fleet returning to India with vast treasures of gold and silver, heavily guarded by cannons and riflemen. He allied with other pirates to ambush the 25-ship Mughal flotilla.
His partner, Captain Thomas Tew, died in battle, allowing Every’s ship, the Fancy, to overtake the Mughal flagship, Ganj-i-Sawai. After a fierce fight and some luck, Every seized the Ganj-i-Sawai, plundering up to £600,000 in valuables. This made him the richest pirate in the world.
The attack strained Anglo-Indian relations, placing a huge bounty on Every’s head, making him the most wanted man. Surprisingly, he retired from piracy to enjoy his spoils. Unlike most pirates, Every was never captured, disappearing from history books, along with his treasure.
William John Cavendish-Scott-Bentinck, 5th Duke of Portland
William John Cavendish-Scott-Bentinck, the Duke of Portland, was a Member of Parliament who lived at Welbeck Abbey. However, he was better known for his eccentricities and a strange paternity suit that emerged nearly two decades after his death.
Lord Cavendish valued his privacy immensely. Rumors suggest he was extremely introverted, with only his valet allowed to see him. He communicated with others through his valet or in writing, instructing servants to ignore him, even if they passed him in the hallway.
His introversion led him underground where he built halls and tunnels under Welbeck Abbey, including a private passage to the station for his carriage. He also constructed a giant ballroom, though he never hosted parties.
Eighteen years after his death, Anna Maria Druce claimed that Cavendish lived a double life as her father-in-law, Thomas Charles Druce, before faking his death. The case dragged on for years, involving an exhumation, perjury charges, and two people committed to an asylum.
General Gregor MacGregor
Gregor MacGregor, of the famous Rob Roy MacGregor clan, lived a life of stark contrasts. He served as an officer in the British Army, fighting in the Napoleonic Wars and rising to the rank of general. Later, he joined Venezuelan forces in their war for independence against Spain, becoming a national hero.
Yet, MacGregor also attempted one of history’s most audacious cons. He claimed to be the Cazique (prince) of Poyais, a country near the Black River. He described the eight-million-acre area as rich and fertile, needing investors and settlers. With Latin American investments popular, MacGregor offered a £200,000 Poyais bond at a six percent return rate.
MacGregor made £1.3 million off Poyais bonds. The problem? Poyais didn’t exist. Many Scottish settlers died in their new “home,” and when word reached London, MacGregor fled to Paris where he tried the con again and was arrested.
Sidney Weinberg
Sidney Weinberg’s story is the epitome of a rags-to-riches saga. Born into a large family of Jewish immigrants, he dropped out of school at 15 to find work.
In 1907, at 16, Weinberg sought work on Wall Street. He entered every office in a tall building at 43 Exchange Place, seeking odd jobs. He landed a position as a janitor’s assistant at Goldman Sachs.
Weinberg impressed Paul Sachs while delivering a flagpole to his residence, earning a promotion to the mailroom. He excelled, attending business school at company expense. By 1927, he became a partner. In 1930, he was named CEO, saving the company from bankruptcy earning the title “Mr. Wall Street,” a position he held for 39 years.
“Red Legs” Greaves
“Red Legs” Greaves’s life unfolds like a swashbuckling adventure. Born in the mid-17th century to Scottish parents exiled to Barbados by Oliver Cromwell, Greaves was sold into slavery. He escaped by stowing away on a ship which unknowingly was a pirate ship commanded by Captain Hawkins.
Discovered, Greaves joined the crew despite despising Hawkins’s cruelty. Eventually, Greaves challenged Hawkins, winning a duel and becoming the new captain.
Greaves was a merciful leader and tried to retire as a plantation farmer after a few successful voyages. However, his past caught up, and he was arrested for piracy in Port Royal in 1692, the year of the massive earthquake that devastated the city.
Greaves survived the earthquake and joined a whaling ship. Later, he became a pirate hunter, earning a royal pardon. He retired to his plantation in Nevis, living happily ever after.
Henry Cyril Paget, 5th Marquess of Anglesey
Henry Cyril Paget, the 5th Marquess of Anglesey, lived a life of extravagance. At 23, he inherited a title, Plas Newydd estate, and a fortune. By 27, it was all gone, and by 29, he died with millions in debt.
Paget spent his wealth on jewelry and luxury clothing. He favored French tailor Charvet and his typical outfit included a lavish dressing gown, numerous jewels, and a headdress. Many items he only wore once.
A theater enthusiast, Paget turned his home chapel into a theater, hiring actors, and starring in lead roles. His snake-like dance earned him the moniker “the Dancing Marquess.”
His lifestyle led to rumors about his sexuality, which his ex-wife dismissed, saying the only person Henry loved was himself.
Julie d’Aubigny, Mademoiselle de Maupin
Julie d’Aubigny, known as Mademoiselle de Maupin, led an adventurous life as a 17th-century opera singer. Her youth involved duels and love affairs throughout the French countryside.
In 1687, at 14, Maupin fled Paris with a fencing master named Sérannes, giving singing and dueling exhibitions. Bored, Maupin began a love affair with a young woman who was then sent to a convent. Maupin followed her, entering the convent as a postulant. She faked her lover’s death by burning a deceased nun’s body in her room, continuing the romance for a few months before moving on.
Maupin returned to Paris and became an opera singer, but she didn’t change her ways. Dressed in men’s clothes, she flirted with a woman at a royal palace party. Three offended suitors challenged her to a duel, and she defeated all three, fleeing the city because duels were banned.
Adrian Carton de Wiart
Adrian Carton de Wiart began his military career in 1899, dropping out of college to fight in the Second Boer War. He was sent home after being shot in the stomach and groin.
At the outbreak of World War I, Carton de Wiart joined the Somaliland Camel Corps where he lost an eye and part of his ear. After his recovery, he acquired a black eye-patch and returned to the European front.
At the Second Battle of Ypres, artillery mangled his left hand, which was then amputated. He then led the 8th Battalion, Gloucestershire Regiment, at the Battle of the Somme, earning the Victoria Cross.
Between wars, he survived a plane crash in Poland. During World War II, in his 60s, he served again, surviving another plane crash in Libya in 1941 and was a POW for two years. Carton de Wiart quipped in his autobiography, “Frankly, I enjoyed the war.”
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