As an entrepreneur, Timothy Dexter was either extremely shrewd or extremely fortunate. Born in Malden, Massachusetts, Unites States on 22 January 1747, his first acquisition was definitely shrewd, if somewhat unromantic. In 1769, aged just 22, he married Elizabeth Frothingham, a wealthy widow ten years his senior, who owned her own house. However, his newly acquired wealth and comfortable home did not endear him to the upper echelons of local society, as he was relatively uneducated and somewhat eccentric. Consequently, he was shunned by the local business community, to such an extent that individuals would go out of their way to offer him bad advice, in the hope of bankrupting him.

However, this was not before Timothy experienced another lucky break, or possibly exhibited a prudent approach to matters of finance, depending on which way you look at it. At the end of the American War of Independence, Dexter purchased large amounts of a virtually worthless currency, known as Continental currency, which had depleted so much during the conflict, that it was regarded as valueless. At the end of the war however, the U.S. government made the decision to pay holders of the currency one percent of its face value. Our young businessman had purchased so much of the stuff, that even one percent of face value, netted him enough profit on his investment to finance the building of two ships. Duly constructed and launched, he thus commenced an export business to the Caribbean and Europe.

Bed warmers, which resembled a frying pan with a long handle and a lid, were popular household items in colder climates, before the advent of central heating. On the advice of one who wished him ill fortune, he took it upon himself to export a large quantity of bed warmers to the West Indies, a region with a tropical climate. Once again, fortune was on his side. The captain of his ship, realising his overlord’s error, marketed them locally as ladles to the molasses industry, which required just such items in the production process, and he was thus able to net his boss a considerable profit.

Timothy Dexter

Another piece of bad advice upon which he acted, was to ship coal to Newcastle, England. In the British Isles, the saying, sending ‘coals to Newcastle’, means to send something to somewhere it is not needed. The case in point being that Newcastle was, at that time, the largest coal distribution centre in Britain. Once again, Timothy’s luck was in, as his ship arrived at a time when miners were taking industrial action by striking, and so his cargo of coal sold for a premium rate.

On another occasion, he was advised to send a large consignment of woollen mittens to the Caribbean, where such items are not required due to the warm nature of the climate. However, as luck would have it, Asian merchants just happened to be in port when the consignment arrived, and they duly bought the lot for export to Siberia, a part of the world where hands need to be kept warm. A similar shipment of gloves he sent to Polynesia, was snapped up by Portuguese traders on their way to China.


Possibly out of jealousy resulting from his extraordinary good fortune, he was snubbed by his social contemporaries, most of whom regarded him as unintelligent and naive. Undeterred by his unpopularity, however, Dexter bought himself an much larger house in Newburyport, Massachusetts and proceeded to decorate it opulently, with minarets and a statue of a golden eagle. More bizarrely, he commissioned 40 wooden statues of famous men, which he placed around the grounds of the house. They included effigies of Thomas Jefferson, George Washington, William Pitt, and Napoleon Bonaparte. He also commissioned a statue of himself with a modest inscription that read “I am the fist in the East, the first in the West, and the greatest philosopher in the Western World.” He also oversaw the construction of his own mausoleum. It was possibly around this time that he also began to refer to himself as Lord Dexter; a title entirely of his own creation.

Timothy Dexter’s House

Another of his strange eccentricities concerned his wife, whom he told visitors had died, despite the fact that she was very much alive and still living in the house. Stunned guests were told that the woman they could see frequenting the property, was actually her ghost. Wondering how people will react to your death, is something most of us will never know the answer to. Not so for Timothy Dexter, who faked his own death in order to find out. About 3,000 people attended his fake wake, but he was not a happy man. Noting that his wife was not crying, Dexter revealed himself to the shocked gathering, and promptly proceeded to beat her for not showing sufficient grief at her loss.

Not content with being a successful, if somewhat odd, businessman, Dexter next turned his attention to writing, and in 1802 published a book entitled A Pickle for the Knowing Ones. In it, he berated politicians, the clergy, and even his long suffering wife. It was terrible. There was no punctuation, and the spelling was unorthodox to put it mildly. As an example, one section begins; “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 goue”. It was so bad that it became popular for its novelty value, and would eventually be reprinted eight times. Responding to criticism surrounding the lack of punctuation, the second edition contained an extra page, purely made up of punctuation marks, which readers were instructed to insert wherever they liked.

Timothy Dexter died for real on 26th October 1806 aged 59, with his will including a bequest for the care of Newburyport’s poor. His obituary contained the comment; “his intellectual endowments not being of the most exalted stamp“, which seems a little ungracious, considering his final act of benevolence. The last word is perhaps best left to nineteenth century author Sarah Anna Emery, who said of Dexter; “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.”

Sources:
https://www.newenglandhistoricalsociety.com/
https://en.wikipedia.org/

Leave a Reply

Your email address will not be published. Required fields are marked *