How Timothy Dexter Turned Ridiculous Ventures Into Riches

19. An Eccentric Businessman

American businessman Timothy Dexter (1747 – 1806) was born in a working class family of modest means in Colonial Massachusetts. He became a tanner’s apprentice at age sixteen, and got pretty good at leatherworking. His life and career revolved around the contrasts between his humble origins, and his desire to join the colony’s elites. Massachusetts’ blue bloods were not receptive to the uncouth and low brow leatherworker’s attempts to join their ranks. So they went out of their way to try and thwart his ambitions and steer him wrong. However, sheer dumb luck allowed Dexter to foil their schemes, and instead succeed time after time.  

18. Humble Beginnings

Timothy Dexter was born in 1747 in Malden, Massachusetts, into a family of Irish descent and modest means. Young Timothy received little education as he grew up. His education ended at age eight, and he was indentured as a servant in a nearby farm. When he turned fourteen, he headed to Charlestown to become apprenticed as a leatherworker. At the end of his apprenticeship, when he was twenty, he met and married a widow, nine years older than himself and with four children. She was rich. Dexter moved into her home in one of the posher parts of Charlestown, and she helped him set up shop in her basement, where he sold leather trousers, gloves, and hides.

17. An Uncouth Upstart

Dexter’s new neighbors included the likes of Thomas Russel, one of Colonial America’s richest men, and John Hancock, then governor of Massachusetts. Such elites did not take kindly to an uneducated and barely literate man who’d married into money. They treated Dexter as an uncouth upstart, which infuriated him. He determined to prove that he was their equal. He noticed that upper class gentlemen often held public office, and decided to secure one for himself. So he badgered nearby Malden for an office. Eventually, after dozens of petitions, they made up a BS position of “Informer of Deer” to get him off their backs. Like the title said, the job was to inform the authorities if deer were spotted in Malden – even though town records indicate that no deer had been seen in a generation.

16. An “Idiot” and a “Fool”?

Timothy Dexter toiled for years, and built up a nest egg of thousands of dollars in savings – a respectable amount back then. His first major break towards financial independence, and it is unclear whether it was a shrewd investment or just dumb luck, came at the end of the American Revolution. He spent his life savings to buy a lot of depreciated Continental currency, both federal and state, which was worthless at the time. Everybody thought he was an idiot and a fool.

15. Beginner’s Luck

Dexter the investor benefited from beginner’s luck, when Congress decided to redeem its wartime notes at 1% of face value. 1% might not seem like much, but it was still a whole lot more than Dexter had paid for those notes. Better yet, Massachusetts redeemed its wartime notes for their full face value. Seemingly overnight, Dexter went from hubby of a rich widow to rich in his own right. Until then, he was an unremarkable businessman, but as seen below, the sudden wealth transformed him into an eccentric dingbat. 

14. A Rich Jerk

Timothy Dexter thought his wealth would finally earn him the respect of his posh neighbors. It did not. Try as he might to break into Boston’s upper crust, his efforts met with repeated failure. Part of it was that those he tried to hobnob with were snobs. A bigger part was that Dexter was, in many ways, a jerk. He had what was described as a “distasteful nature”, was given to “crude rhetoric”, and often blurted the wrong things at inopportune moments.

13. Ditching Boston

Dexter decided that his failure to make it into Boston’s upper society was not because he was a jackass. Instead, he decided it was because the city was too stodgy. So he upped stakes, told his posh neighbors where to shove it, and moved with his wife and family up the coast to Newburyport. There, a series of dumb luck breaks, each stranger than the one before, ensured that he became even richer than he already was.

12. A New Start in Newburyport

Once established in Newburyport, Timothy Dexter decided to become an international businessman, and bought some ships. He also bought a lavish carriage with his initials embossed, and filled a stable with handsome cream-colored horses to pull it. To round it off, he built himself an eighteenth century version of a McMansion, with a great sea view. Dexter’s tastes weren’t classy, and he went for the garish and tacky to furnish and bling it out. However, it was the most expensive garish and tacky stuff that money could buy. It included what passed in those days for the height of comfort in outhouses. On the grounds of his luxury pad, Dexter set up rows of columns, fifteen feet tall or more, and commissioned dozens of wooden statues of famous people to place on top of them.

11. “Lord Timothy Dexter”

A wooden George Washington was prominently displayed in front of Dexter’s door. To his right was John Adams, and to his left, stood Thomas Jefferson. Other columns throughout the grounds were topped with assorted generals, philosophers, politicians, statesmen, Indian chiefs, and the occasional goddess. A statue of Dexter was included in the mix, with an inscription in which he labeled himself “Lord Timothy Dexter“. It added: “I am the first in the East, the first in the West, and the greatest philosopher in the Western world“. Not bad, for a man whose education stopped at age eight, and who had never read a philosophy book. Whatever his faults, the eccentric entrepreneur was not plagued with low self esteem.

10. The Town’s Seediest Mansion

Dexter’s new neighbors in Newburyport disliked him as much as his old ones in Charlestown had. The tacky McMansion with its garish columns topped by wooden statues was bad enough. Worse, Dexter turned his residence into a seedy pleasure dome that locals likened to a brothel. Prostitutes came and went at all hours, long nights of loud and drunken parties became a norm, and the fine interiors, including curtains once owned by a French queen, were soon covered in “unseemly stains, offensive to sight and smell“. His wife bailed out, and moved elsewhere. When Dexter bought ships and announced his intent to get into international trade, fed up neighbors offered him terribly dumb advice, in the hope that he’d bankrupt himself and be forced to move.

9. Exporting Bed-Warming Pans to the Tropics

A neighbor recommended that Dexter export bed-warming pans to the Caribbean – a hot tropical region that did not need bed warmers. Dexter bit, bought 42,000 pans, and shipped them to the Caribbean. The traders laughed themselves to tears at the idiot who’d shipped bed warmers to the tropics. Then their laughter turned to astonishment. Of course, nobody in the Caribbean was interested in the least in bed warmers. However, Dexter’s agent redesignated them as “ladles”, and suddenly sugar and molasses plantation owners could not get enough of them. It would not be the last time that dumb luck allowed Dexter to prosper despite terrible advice.  

8. Sending Coal to Newcastle

On another occasion, rival merchants convinced Timothy Dexter to send coal to Newcastle, England – a city so known for its abundant coal that the term “sending coal to Newcastle” became a byword for futility and stupidity. Once again, however, luck rescued Dexter. His ships, laden with anthracite coal, arrived in Newcastle in the middle of a miners’ strike that had crippled local production. It was one of the few times when Newcastle did not have any coal. Dexter unloaded his sooty cargo at a huge markup, and returned to Massachusetts with “one barrel and a half of silver“.

7. Selling Cats in the Caribbean

Another example was when Newburyport was plagued with stray cats, and a proposal to destroy them all was put to a local vote. It failed, and somebody convinced Dexter that the cats could be sold in the Caribbean. It was a ludicrously dumb idea, but Dexter bit. He advertised in local newspapers that he would pay for stray cats, and promised to treat them well. He shipped them to the Caribbean, where a recent infestation of mice plagued plantations and warehouses. The cats were sold at a premium to eager buyers, and Dexter earned another fortune from a seemingly bonkers idea that nonetheless panned out.

6. Cornering the Market on Corsets

On another occasion, rival merchants talked Timothy Dexter into another seemingly dumb idea in the hopes of ruining him, and got him to invest heavily in whalebones. So he bought 340 tons of whalebones. As it turned out, the dumb investment turned out to not be so dumb. In those days, whalebones were a key ingredient in corsets, and Dexter bought so many of them that he cornered the market. He got to set his own price on whalebones, and unloaded them at a handsome profit.

5. Selling the Good Book

Another dumb investment that rivals talked Dexter into that turned out not to be so dumb and earned him a good return was bibles. Somebody convinced him that the West Indies were in desperate need of The Good Book. So Dexter bought thousands of them in New England for pennies on the dollar, and shipped them to the Caribbean. The demand was low at first, until Dexter began to preach that the locals would go to hell, unless they had a Holy Bible at home. It resonated, and he made a huge profit as a result.

4. A Horrible Husband

Despite the seemingly dumb investments, Dexter’s business career prospered. Not so his marriage. His wife, Elizabeth Dexter, came from a prominent New Hampshire family that included a governor, and they looked down on him. If his frequent womanizing was not enough to wreck his marriage – on one occasion a cuckolded lawyer beat the daylights out of Dexter on the street – his pretending that his wife was dead would have done it. Late in life, Dexter began to refer to Elizabeth as a ghost, and refused to acknowledge that she was alive.

3. A Faked Death

An exception to Dexter’s refusal to acknowledge his wife’s existence was when he faked his death to see how many people would show up for his funeral. The turnout was good, and about 3000 people attended the mock wake. Odds are it was not because of love and respect for the deceased, but because the funeral featured plenty of free food and booze. However, Elizabeth Dexter did not seem sufficiently sad to suit her hubby. So he fell upon her with his cane, until funeral attendees rescued her.

2. Desperation for Recognition

Timothy Dexter grew increasingly desperate for recognition and acceptance. To emulate his rich neighbors, he set up a well-stocked library at home, but hardly ever picked up a book. On the few times he did, he never read for more than ten minutes. When public praise was not forthcoming, he paid a poet to praise him in verse. He also wrote a bizarre book about his life, that featured atrocious spelling and no punctuation. A representative excerpt: “Ime the first Lord in the younited States of A mercary Now of Newburyport it is the voise of the peopel and I cant Help it and so Let it gone Now as I must be Lord there will foller many more Lords pretty soune for it Dont hurt A Cat Nor the mouse Nor the son Nor the water Nor the Eare then goue on all is Easey…”

1.     Just How Dumb Was Timothy Dexter?

Dexter complained about politicians, men of the cloth, and his wife in his book. He self-published the first edition, but incredibly, the book did well. So eight more editions – and paid ones at that – followed. In response to complaints about the lack of punctuation, Dexter added a page to the second edition, with eleven lines of punctuation marks. He instructed readers to help themselves, and insert the punctuations wherever they thought they were needed. Or as he put it, that “thay may peper and solt it as they plese”. When he died in 1806, Dexter’s obituary judged “his intellectual endowments not being of the most exalted stamp”. Still, despite all the dumb moves, he lived the American dream, went from rags to riches, and died in a mansion a very wealthy man. So just how dumb was he, really?

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Where Did We Find This Stuff? Some Sources and Further Reading

Dexter, Timothy – A Pickle for the Knowing Ones (1805)

History Collection – Remarkable Historic Blunders These People Should be Embarrassed About

Historic Ipswich – Lord Timothy Dexter

Knapp, Samuel Lorenzo – Life of Lord Timothy Dexter, With Sketches of the Eccentric Characters that Composed His Associates, Including His Own Writings (1858)

New England Historical Society – Timothy Dexter, the Ridiculous Millionaire Who Sold Coals to Newcastle

Priceonomics – The Strange Life of ‘Lord’ Timothy Dexter