Attempting to sell coal to Newcastle is not typically considered the shrewdest way for a would-be entrepreneur to make a profit or a name for themselves – but ‘Lord’ Timothy Dexter somehow managed both.

Born into relative poverty to a family of farm hands in 1748 in Massachusetts, Dexter – who was only ever a self-styled ‘lord’ – became an apprentice leather craftsman at the age of 16, before moving to Boston at 21 to make and sell gloves and moosehide breeches.

Not long after, revolutionaries triggered a war and decimated the city’s import and export markets by launching the now-infamous Boston Tea Party. 

Despite the challenges this posed, Dexter chose to stay in Boston, where he met and soon married wealthy widow Elizabeth Frothingham – and seemingly fulfilling his childhood dream of joining high society.

Dexter soon realised his neighbours despised him and his eccentric mannerisms, and he campaigned for a seat in public office in a futile effort to win their respect.

Out of pity, he was granted the newly-appointed title of ‘informer of deer’ and placed in charge of monitoring Boston’s deer population.

Deer had not been seen in the area for close to two decades prior to this appointment, and none were reportedly seen during Dexter’s reign either.

Sheer dumb luck

Dexter eventually gave up trying to win favour with his Boston peers and set out for Newburyport, where he again tried to integrate into high society this time through charity, buying up worthless ‘Continental currency’ issued by the 13 US states warring with the United Kingdom from returned soldiers who’d been paid in the currency.

Despite shop owners refusing to accept the currency during the war, the notes became exceedingly valuable after the declaration of independence was signed and Congress agreed to trade the paper currency in for Treasury bonds worth 1% on face value.

The newly-wealthy Dexter used the money to buy two merchant ships and build a garish manor surrounded by statues of history’s greatest men, with a special statue of himself placed right alongside them.

His neighbours hated the house, and Dexter, and tried to sabotage him by persuading the barely-literate man to try selling bed warmers in the tropical West Indies.

While a less fortunate man might have bankrupted himself on such an endeavour, Dexter managed to sell the bed warmers to the local molasses industry as much-needed ladles.

He sold all 42,000 in his inventory for a 79% mark-up and sailed back to Massachusetts even richer than before.

Following his success, a rival merchant tricked Dexter into taking coal to Newcastle where, fortuitously, the miners were striking.

Once again, he sold his wares at a profit.

Dexter then bought bibles for less than half price and sailed them to the West Indies, where he persuaded locals they would be damned to an eternity in hell if they didn’t purchase the holy books and made a handsome sum.

In one similarly insane instance, Dexter reportedly collected up stray cats that were plaguing his hometown and sold them in the Carribean as a solution to a recent rat infestation.

By this point, Dexter began describing himself a master of ‘spekkelation’ (that’s ‘speculation’, to you or me).

A ghost, a funeral, and a book

His eccentricities and his relationship with his wife had worsened greatly by this point.

Dexter began telling friends his wife had died and the very real, very alive woman living with him in his mansion was in fact, her ghost.

On one occasion Dexter faked his own death to see how his friends would react, and when he discovered his wife – understandably dry-eyed and smiling – mingling among the 3,000 strong crowd, he promptly caned her.

It was around this time Dexter wrote a book, A Pickle for the Knowing Ones, in which he taunted the intelligentsia of the day.

The book was horribly spelled and featured no punctuation, but was nevertheless a hit and was reprinted numerous times – albeit these subsequent editions featured a page of punctuation marks at the back of the book which readers could “salt and pepper” throughout the book as needed.

Then, in 1806, Dexter passed away for the second and final time, drawing to a close one of the strangest chapters in American capitalism’s history.

Sources:

• New England Historical Society, Timothy Dexter, the Ridiculous Millionaire Who Sold Coals to Newcastle
• Priceonomics, The Strange Life of ‘Lord’ Timothy Dexter