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Timothy Dexter and the Luck of the Irish

I've spent half a century writing for radio and print (mostly print). I hope to still be tapping the keys as I take my last breath.

Born to an Irish immigrant family in New England in 1747, Timothy Dexter is usually described first as a businessman, but he was more than that, a lot more.

An engraving of Timothy Dexter shortly before he died.

An engraving of Timothy Dexter shortly before he died.

The Rags to Riches Story

By the time he was eight years old, Timothy Dexter was out of school and working as a farm labourer. After a few years, he went into the tanning trade as an apprentice.

Fully qualified, he turned up in Charlestown, the centre of Boston’s leather industry. The town was enjoying a boom and it was just the place for a man with Dexter’s feral skills to prosper.

At the age of 23, he married Elizabeth Frothingham, who was a 32-year-old widow. She had a couple of attributes that Dexter found appealing―wealth and a house. He opened a business in the basement selling leather goods.

He prospered mightily and put thousands of dollars into Continental Currency that was used to fund the Revolutionary War. He paid fractions of a penny for each dollar of this “money.”

Continental Currency was issued by the Continental Congress in 1775 to pay for the war of independence from Britain. It was not backed by any assets and became almost valueless. In 1792, under Alexander Hamilton, the federal government exchanged continentals for U.S. dollars at one percent of face value.

When Dexter’s worthless scrip turned into real money he became a wealthy man. This was one example of the man’s incredible good luck, or did he, as has been suggested, have inside information?

Continental Currency.

Continental Currency.

Timothy Dexter: the Lucky Entrepreneur

The Phrase Finder tells us that “To carry coals to Newcastle is to undertake something which is both unnecessary and pointless.” Not in the case of Timothy Dexter.

He did not make friends easily; in fact, through crass behaviour he alienated just about everybody he came across. Members of the business community disliked him intensely and tried to bankrupt him by getting him to undertake ventures they were sure would fail.

Acting on the advice of a rival, Dexter sent a shipload of coal to Newcastle. He was unaware that the British city had a large coal mine of its own. But such was Dexter’s good fortune that his ship arrived when Newcastle’s coal mine was shut down due to a strike and he was able to sell his cargo at a handsome profit.

Next he was persuaded that selling warming pans to the Caribbean was a money-making venture. He bought 42,000 of these pans attached to long handles that were used to warm the beds of people living in cold climes; not something you’d expect to be in high demand in the Tropics.

But, good grief, the folks in the West Indies found the pans to be perfect ladles for use in the molasses industry. More profit for the hayseed who was completely ignorant of geography and climate.

The pan filled with hot coals was not in high demand in the Caribbean for its original purpose.

The pan filled with hot coals was not in high demand in the Caribbean for its original purpose.

The New England Historical Society notes some of his other unexpected trading successes: “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.”

Man of Letters: Just Not the Right Ones

With only three or so years of education, Dexter deemed he was well qualified to be a writer. In 1797, he published A Pickle for the Knowing Ones. Basically, it was a grumble of almost 9,000 words, with his wife, the clergy, and politicians as the objects of his scorn.

He troubled himself not at all with spelling, grammar, capitalization, or punctuation. He gave the book away free but it became strangely popular and went into eight printings.

There were complaints about his butchery of the English language so in a subsequent edition he included a page with nothing on it but punctuation marks. He advised readers they were free to insert commas, periods, etc., wherever they felt them necessary.

Let’s have a sample of Dexter’s prose; this is the opening of his book so you have fair warning what you are in for if you wish to proceed (link below): “Ime the first lord in the younited States of A mercary Now of Newburyport it is the voise of the people and I cant Help it . . .”

Failed Social Climber

Timothy Dexter’s big weakness was that he craved acceptance by society’s elites. But, the upper crust was just as keen to make sure he didn’t join their ranks.

He may have hoped that his wealth would buy him a place among the crème de la crème. He bought a mansion as a signal that he belonged on millionaire’s row, but his taste in decoration was deemed to be tacky.

He had 40 wooden statues erected in his garden―the likes of John Hancock, Indian chiefs, Adam and Eve, and Louis XVI were displayed in garish paint schemes.

Dexter's mansion surrounded by his tasteless statuary.

Dexter's mansion surrounded by his tasteless statuary.

He even bestowed upon himself the title of “Lord.”

In a biography of Dexter written several decades after his death, William Cleaves Todd listed some of the character flaws that made the man unacceptable in polite society: He was “vain, uneducated, weak, coarse, drunken, cunning man, low in his tastes and habits, constantly striving for foolish display and attention, but, with all his folly, having business shrewdness, to which, and not to luck, he owed his success.”

He was not able to elbow his was into the upper class before his death in 1806 at the age of 69.

Bonus Factoids

  • One of the things that Timothy Dexter did to emulate those in high society was to build and stock a library in his house though he could barely read.
  • Learning that the king of England had a poet laureate, Dexter hired one for himself. A 20 year-old was elevated from selling halibut to writing fawning verses about his employer.
  • The bulk of Dexter’s fortune came from his reckless gamble on Continental Currency. In its time, “Not worth a Continental” was a phrase used to describe anything that was of no value.
  • Dexter had two children of whom the New England Historical Society wrote, “The son became a half-mad drunk, the daughter became a completely mad drunk.”
  • Pickle for the Knowing Ones.


  • “The ‘Literary’ Legacy of Lord Timothy Dexter.” Paul Collins, National Public Radio, January 22, 2005.
  • “Continentals.” James Chen, Investopedia, October 3, 2019.
  • “The Strange Life of ‘Lord’ Timothy Dexter.” Zachary Crockett,, January 9, 2015.
  • “Lord Timothy Dexter.” William Cleaves Todd, Press of David Clapp and Son, 1886.

This content is accurate and true to the best of the author’s knowledge and is not meant to substitute for formal and individualized advice from a qualified professional.

© 2021 Rupert Taylor

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