Timothy Dexter was considered a lucky fool for selling coal to Newcastle and bed warmers to the tropics – and somehow making money on the ventures.

He rounded up the stray cats of Federalist Newburyport, Mass., shipped them off to the Caribbean – and made money.

He wrote a semiliterate book without any punctuation – and it went into eight printings.

Timothy Dexter failed at the one thing that mattered most to him: acceptance by high society. Perhaps it was because he was vain and ridiculous, or perhaps because he was unlettered and crude.

Timothy Dexter

Timothy Dexter was born in Malden, Mass., on Jan. 22, 1747. The first Dexter had immigrated from Ireland a century before. His family was poor and young Timothy received little education.

He went to work on a farm at the age of eight. At 14 he left the farm for Charleston, S.C., to work as an apprentice dressing leather for breeches and gloves. He finished his apprenticeship in Boston. As was the custom, his employer on his last day gave him a freeman suit, which he sold for eight dollars and 20 cents.

He walked to the boom town of Newburyport, where residents prospered from shipbuilding and trade. Within a year he bought land, married Elizabeth Frothingham, a rich widow nine years older than he. She had four children and a house.

Dexter set up shop in the basement of his wife’s house, selling leather trousers, gloves, hides and blubber. By the end of the American Revolution he had saved several thousand dollars. He spent it all on worthless Continental currency. When Congress decided to make good on the scrip, Dexter became a very rich man. He may have been lucky, or he may have had inside information on Congress’ intentions.

Cats and Bed Warmers

He bought a magnificent house on State Street that had belonged to Nathaniel Tracy and is now the Newburyport Public Library. He built two ships, and sent bed warmers in them to the West Indies where they were used as ladles in the molasses industry.

Lord Dexter gathered up stray cats and sent them to the Caribbean, where warehouse owners bought them to catch mice.

He sent gloves to Polynesia, where Portuguese traders bought them on their way to China.

He bought up huge amounts of whalebone for stays just as the French fashions arrived featuring large corsets.

But he couldn’t have the one thing he really wanted: acceptance by high society. High society shunned him. Wrote one critic, “For what purpose are riches given to some men unless to display in more glowing colours the disgusting deformities of their Characters?”

Coals to Newcastle

Timothy Dexter achieved one of his greatest business coups because someone tried to make him the butt of a joke. He was told to ship coals to Newcastle.

Dexter did, and his ship arrived just as the Newcastle coal miners were striking. His coal sold at a premium.

One of his defenders argued he was a shrewd businessman, rather than lucky, but a ‘vain, uneducated, weak, coarse, drunken, cunning man, low in his tastes and habits, constantly striving for foolish display and attention.’

Irving Wallace noted Timothy Dexter’s fortune was founded on sobriety and a hangover. He never drank in the morning and he never conducted business in the afternoon.

Among Dexter’s detractors was his wife, who took to nagging him about his harebrained ventures despite their success. He began to call her a ghost and refused to acknowledge she was alive.

They had two children, Samuel and Nancy. The son became a half-mad drunk, the daughter became a completely mad drunk.

Lord Dexter

Tired of being socially ostracized, Dexter sold the Tracy house in 1796 and bought an estate in Chester, N.H. He began to refer to himself as ‘Lord Timothy Dexter.’ He pursued women, possibly the reason a lawyer waylaid him and beat him savagely.

After his assault, Lord Dexter returned to Newburyport. He bought a princely estate once owned by Jonathan Jackson, Nathaniel Tracy’s business partner.

He created an outdoor museum on the grounds with 40 garishly painted wooden images of such diverse figures as Louis XVI, Adam and Eve, Toussaint Louverture and John Hancock. It attracted many visitors, including pretty young damsels with whom Dexter tried improper liberties.

Lord Dexter filled his house with eccentrics, including Madam Hooper, the mistress of a British officer with a double set of teeth and a chicken for a companion; Molly Pitcher, who supposedly fired a cannon in the Battle of Monmouth and became a fortuneteller; Jonathan Plummer, a fishmonger and purveyor of pornography who wrote poems about Dexter’s greatness.

Dexter published a 24-page book in 1802 that criticized the clergy, politicians and his wife and had no punctuation. He called it A Pickle for the Knowing Ones (you can read the whole thing here). He handed the book out for free, but it became popular and was reprinted eight times. In the second edition, Dexter added a page that consisted of 13 lines of punctuation marks with instructions the readers could distribute them as they pleased.

Irving Wallace described it as ‘an egotistical, opinionated, coarse defense of Dexter, by Dexter, against all “Enemys” who were anti-Dexter.’

Funeral

Shortly before Dexter died, he staged his own funeral, bribing his family to go along with the ruse. He wanted to see how people would react. He beat his wife afterward because she didn’t cry enough.

Lord Timothy Dexter died at age 59 on Oct. 26, 1806, leaving money for the care of Newburyport’s poor. The statues were damaged in the storm of 1815 and sold for a few dollars at auction. Those that weren’t sold were burned.

The Timothy Dexter house became a tavern, and then went through a series of owners. In 1988, painters set it on fire by removing paint with a torch. The cupola and golden eagle on the roof were destroyed, but the Society for the Preservation of New England Architecture had the original blueprints. The house was rebuilt.

Years after he died, Sarah Anna Emery described Dexter in Reminiscences of a Newburyport Nonagenarian. “Though ignorant and illiterate, and doubtless somewhat indebted to luck for his good fortune, still it is evident the man was both shrewd and sagacious,” she wrote.