Timothy Dexter, the Ridiculous Millionaire Who Sold Coals to Newcastle

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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. He did, after all, call himself a lord and stage his own mock funeral and surround his High Street mansion with painted wooden statues of the great men of history.

But the question still lingers even to this day: Was he incredibly lucky or incredibly shrewd?

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 had little money and young Timothy received little education.

He went to work as an indentured servant on a farm at the age of eight. At 14 he left the farm for Charlestown, Mass., to work as an apprentice dressing leather for breeches and gloves. When he finished his apprenticeship, his employer gave him a new suit of clothes, called a freedom suit.

Novelist John P. Marquand, another son of Newburyport, wrote two books about Timothy Dexter. The first repeated the legend, the second, Timothy Dexter Revisited, offered a more sympathetic view of the man.  In Dexter’s case, noted Marquand, he received a good freedom suit. That “proves that Dexter had been sober and diligent,” Marquand wrote. “In fact, all evidence indicates that he was quiet and industrious for many years after his arrival in Newburyport, and not conspicuous until he suddenly made a fortune.”

Newburyport

Dexter sold his freedom suit for eight dollars and 20 cents, which helped pay for his relocation to Newburyport sometime around 1767. At that time the seaport town attracted many artisans and tradesmen. Business boomed and Newburyport rivaled Boston in commercial importance. In 1767, Newburyport’s shipbuilders built 70 vessels.

Within a year Dexter bought land and married Elizabeth Frothingham, a modestly well-off widow nine years older than he. She had four children and a house.

He set up shop in the basement of his wife’s house, selling moosehide trousers, gloves, hides and blubber.  Elizabeth also opened a shop selling notions.

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. Lucky or shrewd?

Sudden Wealth

When Dexter suddenly came into his fortune in 1791 or 1792, he lost his moorings, according to Marquand. He and his wife had toiled steadily for more than 20 years. He had risen by his own efforts in a competitive marketplace and won respect as a businessmen. But now as a man of considerable means, the Timothy Dexter of legend and lore came into view.

Something, wrote Marquand, encouraged the fantastic side of Timothy Dexter’s temperament.

Cats and Bed Warmers

He bought a magnificent house on State Street that had belonged to Nathaniel Tracy and now serves the Newburyport Public Library. He built two ships, the Mehitabel and the Congress.  Stories are still told of the improbable — and lucky — trades he made.

He famously shipped coals to Newcastle, where they sold at a premium during a coal miner’s strike.

He once sent bed warmers to the tropical West Indies, where they found a use as tools in the molasses industry.

One year, Newburyport had a problem with stray cats. Town Meeting voted on an article to destroy them all. The motion failed by a vote of 50-50. The next day, Dexter put an ad in the paper offering to pay for stray cats and promising to treat them well. He sent them to the Caribbean, where warehouse owners paid a premium for them. Dexter may or may not have known about the infestation of mice bedeviling the plantations.

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

He claimed he cornered the whalebone market just as the French fashion for large corsets — or was it hoop skirts? — arrived.

But like many wealthy people, Dexter may have wanted to bend the truth just a bit about how he made his money.

Trouble at Home

Life at home in the Tracy mansion did not match Timothy Dexter’s business success. His hot-tempered wife scolded him often, not without cause. He had a roving eye and drank far too much.

Elizabeth Dexter probably contributed to his need for acceptance. She came from the New Hampshire Gilman family, which had produced a governor, John Taylor Gilman. Timothy Dexter had had real estate dealings with his wife’s family, and they probably looked down on him. He began to call her a ghost and refused to acknowledge she was alive.

They had two children, Samuel and Nancy. Dexter hoped Samuel would turn into an educated gentleman. Instead, he turned into a reckless drunk. Sam convinced his father to let him take one of his ships to England to sell the cargo. Instead, he blew it all at the gambling table.

Nancy had beauty but no brains. She married Abraham Bishop, a Yale scholar with little money, and moved to New Haven with him. The marriage failed, he beat her and she took to drinking heavily. Alcohol did not improve her already feeble wits, so Nancy returned home where her family shut her away.

Amidst these troubles, Timothy Dexter claimed he grew increasingly “nervous.” And so he sold the Tracy house in 1796 and decamped to Chester, N.H.

Earl of Chester

Despite his drinking, Dexter still had business sense. Irving Wallace noted Timothy Dexter founded his fortune on sobriety and a hangover. He never drank in the morning and he never conducted business in the afternoon.

Marquand speculated he moved to Chester, a thriving mercantile town, to invest in real estate. Whatever the case, he took to calling himself the Earl of Chester. A child who called him “Lord Dexter” could expect a quarter, an adult, perhaps dinner and drinks.

He continued to pursue women, possibly the reason a lawyer waylaid him and beat him savagely.

Lord Dexter

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 statues of such diverse figures as Louis XVI, Adam and Eve, Toussaint Louverture and John Hancock. The first three U.S. presidents stood astride a giant arch. Dexter had at least one statue of himself, with the motto, “I am the first in the East, I am the first in the West, and the greatest philosopher in the western world.”

Marquand believed Dexter’s madness had a method. He had invested in the Essex-Merrimack Bridge, and traffic was falling off. Dexter, thought Marquand, was trying to increase traffic across the bridge with his “outdoor museum.” It did attract many visitors, including pretty young damsels with whom Dexter tried improper liberties.

As his drinking and tempter worsened, Lord Dexter turned to eccentrics and sycophants for praise and comfort. Madame Hooper, for example, had a double set of teeth and a chicken for a companion. She told his fortune. Jonathan Plummer, a fishmonger and purveyor of pornography, wrote poems about Dexter’s greatness. He also had a little dog, probably a Mexican hairless, who never left his side when he was drunk.

In 1802, Dexter published a 24-page book that criticized the clergy, politicians and his wife. Full of misspellngs, it 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 grew popular and went through eight reprintings. 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.

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 storm of 1815 damaged the statues, and they 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. Marquand noted that several wealthy families lived in it and added Victorian embellishments. It was hard, he wrote, to tell where Dexter left off and the Victorians started.

In 1988, painters set it on fire by removing paint with a torch. The fire destroyed the cupola and golden eagle on the roof, but the Society for the Preservation of New England Architecture (now Historic new England) had the original blueprints. The house was rebuilt, and is now privately owned.

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.

Watch the author of this story discuss Timothy Dexter here.

This story was updated in 2024.