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Lord Timothy Dexter

And his Strange and Unfortunate Life

Article by Cody PenningtonMay 1, 2020

Lord Timothy Dexter was an uneducated man born in the 1700s that embodied luck and fortune. But wealth can only take you so far, which Dexter never quite seemed to learn.

Article by Cody PenningtonMay 1, 2020

Lord Timothy Dexter was an uneducated man born in the 1700s that embodied luck and fortune. But wealth can only take you so far, which Dexter never quite seemed to learn.

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Lord Timothy Dexter was born in 1743 in Malden, near Boston. He was born into a family of farm labourers, effectively birthing him into the lower class. A fact which haunted Timothy to his dying day.


In his late teens, Timothy undertook an apprenticeship with a leather dresser in his hometown. Interestingly, this occupation, though still considered a lower class job, was quite profitable for Dexter’s station. Further, luckily for Timothy, the leather dressers in the Boston area, including his teachers, had become very proficient in the art of crafting Moroccan Leather, which was very in vogue with the colonial fashionistas at the time. Effectively, the Bostonian leather dressers had monopolised the market for this Moroccan Leather and their skills were passed directly to Timothy, placing him in one of his earliest lucky moments; of which he would have many throughout his life.


Following the completion of his apprenticeship at the age of 21, Dexter decided to go into business for himself making use of his in-demand leather dressing abilities. However, the situation in Boston at this time was very unstable. For a bit of context, at this moment in World History, America and Great Britain’s relationship was becoming very strained. Britain was suffering financially due to the recent French and Indian War (a war to decide who would rule North America) and Britain felt that America should help foot the bill. This brought in many legislative acts from Britain to America implementing taxes on many different goods.




America felt that this was unfair due to the fact that no representatives in America were allowed to represent America in Parliament to argue these taxes. This led to America’s fight against “taxation without representation”, which further led to the Boston Tea Party, which in turn led to the American Revolution.


Boston Tea Party

British legislation was enacted to allow the British East India Company to sell tea from China in America effectively tax-free (pay tax and receive a refund), while simultaneously charging the American colonists a hidden tax on each pound of tea, which would be paid to Britain. American colonists discovered the tax and stormed the East India Company ships and threw 92,000 pounds of tea into the ocean. This event along with other unfortunate events lead to the Revolutionary War.


As the country fell into the Revolutionary War, Timothy decided to take his marketable skills of leather dressing to the nearby hub of Charlestown (which was 4 miles from his home). Making full use of the skills he developed during his apprenticeship, Timothy quickly found a decent amount of success. As luck would have it, his skills were somewhat recession-proof, so he continued to see a rise in profits.


Timothy Dexter was undoubtedly one of the most fortunate (and eventually unfortunate) people from all of history. We will be using the terms “luck”, “lucky”, and other similar terms a lot throughout this article, because those were the most descriptive words to use for Lord Timothy Dexter. He was obviously lucky that his career continued to grow throughout one of history’s most important wars, but he was also very lucky with his move to Charlestown. Not just due to his rising profits, but also due to the fact that he met and somehow wooed his wife, Elizabeth Frothingham.




Marrying Elizabeth

Elizabeth Frothingham was a wealthy widow of one of Dexter’s former leather associates. However, she is not just wealthy. She was incredibly wealthy, especially in comparison to Timothy. Elizabeth had developed her fortune as a huckster, selling goods door to door. (Before I say this point, I have to say that I believe wholeheartedly in equality between the sexes.) But in a time where there were certain expectations on women inside a household, this feat is unbelievably impressive. Obviously, women were expected to raise the children and care for the home (again, not my view on how things should be). But Elizabeth’s industrious aptitude must be described at least to give her the credit she deserves. But Timothy did not necessarily see in Elizabeth a strong wife. Timothy’s choice to marry Elizabeth has been argued as simply a financial one.


Following their marriage, Dexter set out to ingratiate himself into the upper class of Charlestown. Having come from somewhat humble beginnings, and then coming into money, albeit mostly by marriage, Timothy felt a constant need to progress in his professional life and to be seen as one of America’s nobility, or, in other words, to be accepted by them. His neighbours in Charlestown included incredibly influential people of American history, such as John Hancock and Thomas Russel (one of the richest men in the country at the time). Being typically upper class, these men were well-versed in etiquette and business affairs; to which Dexter was not. He was severely uneducated and had left school at the age of 8. He was described as a loud-mouth person, eccentric, crude and distasteful. And as he had come from a lower-class family and merely married into money, he was not accepted whatsoever. This infuriated him and only made him crave acceptance more.


To put himself on the same tier as his neighbours, Dexter noticed quite quickly that they all seemed to have a common attribute. Many of his neighbours had either held, were holding, or worked in some way related to public offices. So, he decided to dive right into politics. He did so by quite literally bombarding his previous hometown’s (Malden) governing body with dozens of petitions until they finally relented and created a post for him. He was then known as the “Informer of Deer”. This required Dexter to keep track of the town’s fawn populations. However, the town’s government records show that the “last deer had disappeared from the Malden woods nineteen years before.” This fact seems to have been lost on Timothy, as he was quite satisfied with his new duty, obviously only seeking the position to gain clout.


With his political position satisfied, Dexter then decided to try to multiply his wealth, which he did in very odd ways.




Continental Dollar (First Stroke of Luck)

As we mentioned earlier, America and Great Britain had been on the verge and at the beginning of the Revolutionary War. During the onset of the war, Congress issued America’s first form of paper currency, as it had been coins of silver and similar up to this point. This paper currency was referred to as the “Continental dollar” which ranged widely in value from ⅙ of a dollar to $80. During the revolution, the currency’s value fell drastically, and even though Congress had issued millions of dollars worth of these bills, many vendors refused to accept them. This cycle of printing the bills and them not being accepted continued until the currency’s value fell to an all-time low. Due to this the phrase “Not worth a Continental” became a common phrase used to describe an utter lack of value in goods.


Soon, veterans of the war began to return home, and can you guess which currency the government decided to pay them for their service? The Continental Dollar. Because of this, the veterans were destitute, and, interestingly, this could have possibly begun the situation of veteran homelessness that perpetuates in America to this day. To boost public confidence and to do a good deed, Dexter’s aforementioned neighbours, Hancock and Russel, took it upon themselves to actually buy back some of these bills.


Dexter decided to emulate them, but he decided to take it further. Since he saw how willing Americans were to part with the currency for literally any amount, he took all of his savings, as well as all of his wife’s savings, and purchased an enormous amount of the currency for literal pennies on the dollar. This move was very...very...dumb. There was no possible evidence showing that this currency would actually be reinstated. He gambled his entire livelihood, and his family’s, simply because he yearned for the respect of his peers.


However, as we said earlier, he was ridiculously lucky, and his gamble proved fruitful. Once the US Constitution was ratified, it was stipulated that Continental dollars could be traded in for treasury bonds at 1% of their face value. Because he had purchased an insane amount of the Continentals, Dexter had instantly and astronomically increased his fortune.


Even further to that, he was given advice by a neighbour (who, I must add, did not like him) to purchase large quantities of European currencies. Which now, due to the new Constitution, he was able to flip for a further profit.




Moving to Newburyport

With this incredible envious fortune, Dexter believed he would finally gain credibility within the elite circles of Boston. However, this is the one area of his life where he lacked luck. Ultimately, Dexter, likely very hurt, decided that his rejection had more to do with the Bostonians’ stodgy nature, and not his own eccentricity. So, he gathered his family and moved north to the coastal town of Newburyport, where his luck only grew, at least in matters of business.


Records say that Newburyport was an idyllic town, where rich and poor intermingled and where the population was not so large as to hide any individual, however odd or humble. Even with this knowledge, Dexter aimed to make a spectacle from the moment he arrived.


He purchased a fleet of shipping vessels, a stable of cream-coloured horses, and a lavish coach complete with his initials on the side. He then built a chateau fit for a prince overlooking the sea, which was filled with the most lavish furnishings money could buy, including tasteful and commodious outhouses.


Historian Samuell L. Knapp recounted that Dexter also commissioned the carving and mounting of more than 40 giant, wooden statues on his property, each depicting a great character of American lore. Knapp describes the estate as follows:


“...The tasteless owner, in his rage for notoriety, created rows of columns, fifteen high feet at least, on which to place colossal [statues] carved in wood. Directly in front of the door of the house, on a Roman arch of great beauty and taste, stood general Washington in his military garb. On his left was Jefferson; on his right, Adams. On the columns in the garden there were figures of indian chiefs, military generals, philosophers, politicians, statesmen...and the goddesses of Fame and Liberty.”


Finally, Dexter erected a final statue of himself. He then painted an inscription beneath it that read, “I am the first in the East, the first in the West, and the greatest philosopher in the Western world”, although he had never done or contributed anything to do with Philosophy in any way.


Each statute cost $2,000, and the combined total added up to twice the amount Dexter had paid for the entire estate, but the statutes did garner the public’s attention which was Timothy’s only goal.


Unfortunately, likely tired of Dexter’s eccentricity, constant fighting for fame and acceptance, and living in an eyesore of a home, Elizabeth grew tired of the embarrassment and moved to another estate in the neighbourhood, leaving behind Dexter’s son.


Similar to Dexter, his son had no interest in learning. And soon, what was previously the family home had been turned into somewhat of a brothel: which included long nights of drinking, in which women came and went, and the previously fine interiors (including curtains that were once owned by the Queen of France) became covered in “unseemly stains, offensive to sight and smell.”




Shipping Business

As we mentioned earlier, Dexter had purchased a fleet of ships for seemingly no reason. But he soon announced that he had intentions to launch a business in international trade. His neighbours, likely tired of his new bachelor ways and his old eccentricities, decided to use this as an opportunity to bankrupt him, in the hopes that he would then be forced to move.


The plan was to provide Dexter with terrible investment opportunities. In one particular interest, a neighbour suggested that Dexter should sell warming pans in the West Indies. Warming pans were flat pans placed under mattresses to warm beds, and the West Indies is an area of islands known for their year-round hot weather. Dexter, obviously not affluent enough to research this opportunity, quickly decided to try his hand and purchased 42,000 of the pans. For this, he needed nine shipping vessels to carry them. He quickly set off to sell the pans, all while the experienced traders were laughing behind his back.


When he arrived in the West Indies, he quickly found that there was no use for bed warmers. However, somewhat ingeniously, he decided to rebrand the pans as ladles. He then sold them to sugar and molasses plantation owners in the area. He found that the demand was so great that the owners would buy three or four at a time. Dexter marked up the pans by 79%, sold them all, and returned home with an even greater fortune.


In another unfortunate trick on Dexter, a trader maliciously convinced him that there was a great demand for coal in Newcastle. However, Dexter again did not have the foresight to research this further. If he had, he would have known that there was already a very well-established coal mine in Newcastle, meaning that any foreign shipment was completely useless. When Dexter arrived, however, he found that the coalmine, miraculously, was on strike. There was an enormous need for his coal. He sold the coal for another huge mark-up and, once again, returned home with an even larger fortune.


It was around this time that some historians believe Dexter actually developed a business intellect and knowledge of trading techniques. It is argued that his choices from this moment on were not simply based on stupidity or ignorance but rather ploys to dupe his doubters. He began to notice that he could simply find a good that was scarce in a market, purchase it, then double the price and sell it. Although he had gained this insight into the business world, he still decided to carry on in a typical Dexterous fashion, performing his business strategy with incredibly odd goods.


At one point, he decided to purchase 340 tons of whalebone. Because of this, Dexter effectively monopolised the entire whalebone market. And, in yet another ridiculous stroke of good luck, whalebone went on to be used in multitudes of goods, including corsets, toys, and typewriters. It was such a popular commodity that it is still, to this day, known as the “plastic of the 1800s.”




Call Me “Lord”

Although Dexter had amassed a ridiculous fortune, he still yearned to be accepted by the elite upper-class. He had not just made a name for himself in Newburyport, he was also well known for his eccentricities far beyond his coastal town. Although his goal was to be considered a noble gentleman, his actions constantly kept him from that moniker.


He would continue to emulate his wealthy neighbours. He purchased an incredibly lavish library of books, which he never read more than ten minutes at any given time. When he learned English nobility enjoyed paintings, he ordered a servant to purchase a brilliant collection. None of these attempts worked in Dexter’s favour. And since he had not yet gained noble friends, he surrounded himself with the most eccentric characters he could find.


Of these were: John P., a failed headmaster who opened his own school and taught science, although he had no knowledge of the subject whatsoever; Madam Hooper, a rich local widow who was now a fortune-teller who would give Dexter astrology advice in exchange for tea; and a 20-year-old halibut salesman whom Dexter decided to hire as his personal poet laureate.


Soon, Dexter also declared himself as Lord and instructed his servants, guardsmen, and friends to refer to him as such. Thus, he became Lord Timothy Dexter.


However, even with this forced adulation from his servants and peers, Dexter knew that there was still a lack of respect for him. So, as most level-headed people would do, he decided to fake his own death, in an attempt to throw a fake funeral to see how the public really felt about him. But it must be said that we are not sure of his mental capacity at this time. Some believe that Dexter began to truly lose his mind, but this is difficult to determine when you compare this decision to his usual eccentricities.


But nonetheless, Dexter began his funeral preparations by building a grandiose tomb that occupied the entire basement of a summer home. He then hired the best cabinet maker to craft a coffin of the finest mahogany available, which was found to be so well-made that Dexter actually slept in it for several weeks.


For his ruse to work, Dexter entrusted a few of his men to plan the mock funeral and to hand out small cards showing the news of Dexter’s death to everyone in the community. Dexter also let his wife and children in on the hoax but demanded that they “act the part.” Specifically, he wanted them to appear completely distraught over his parting.


As far as funerals go, Dexter’s was actually somewhat of a success. 3,000 people showed up and it was a grand affair, with exotic liquors and the finest wines. I suppose it can’t be known whether the whole 3,000 attended to mourn or to celebrate, but either way, Dexter felt the day was a success.


That is until he saw his wife. Dexter’s children were playing their part successfully, with his son drunk enough to weep and his daughter burying her head in her hands. But Dexter’s wife was completely tear-less and smiling ear to ear.


Dexter approached his wife secretly in the kitchen, confronted her and callously “caned” her for her apparent lack of effort, which caused a great commotion. Guests entered the kitchen to investigate the scene and found the supposedly-dead Dexter, smiling like a child who’d just been caught doing a bad deed. He then proceeded to go about his own funeral speaking to the mourners as if the entire thing had never happened.




A Pickle for the Knowing Ones

The years following Dexter’s first funeral were filled with similar eccentric activities. He decided that his next big pursuit would be to achieve immortality, and to do so, he would follow in the footsteps of many of those he admired and publish a memoir.


As we said earlier, Dexter was severely uneducated, having left school at the age of 8. He had no knowledge of writing or penmanship, but still set up to produce a written work to rival Shakespeare. He titled his book “A Pickle for the Knowing Ones, or Plain Truths in a Homespun Dress”.


The book was grossly misspelled, and completely lacking any sort of punctuation. This made the entire work a completely incomprehensible mess. As an example, here are a few lines from the beginning of the book:


To mankind at Large the time is Com at Last the grat day of Regoising what is that why I will tell you thous three kings is Rased Rased you meane should know Rased on the first Royal Arch in the world olmost Not quite but very hiw up upon so thay are good mark to be scene so the womans Lik to see the frount and all people Loves to see them as the quakers will Com and peape slyly


Instead of selling his work, Dexter decided to hand out the book to people on the street. To the surprise of many, it became very popular and demanded a second printing. In response to the criticism that he had not added enough punctuation, Dexter included in the second publishing a full page of punctuation as the final page of the book. On the this page he instructed the reader to salt and pepper the marks as they wish.


Almost a century after the books release, Dexter still received praise (if not somewhat satirical) for his memoir. His book still received reviews in monthly printings, possibly making it more of a success than Dexter had even thought.



On October 26, 1806, just a few years after publishing his book, Lord Timothy Dexter passed away for the final time.


In his final days, he sought to right his wrongs and atone for his errors through the use of his will. His estate was divvied up equally between his children, wife, and friends, and all were said to be very happy with the outcome. His wooden statues were unfortunately knocked lose by a strong gale of wind, and only fetched 50 cents to $5, although having been commissioned at $2,000 each.


Perhaps the saddest moment in Dexter’s life was the end. It could have been an attempt to truly erase Dexter from the town’s history, but Newburyport’s Board of Health rejected Dexter’s final request to be buried in the tomb he’d built years earlier for his fake funeral. Their reasoning was due to it be unsanitary. The Lord was instead laid to rest in a small cemetery in the hills, where his headstone was quickly covered in wheatgrass, symbolically erasing his name from history.


I suppose you have to admire Dexter’s appreciation for his own eccentricity. Biographer Samuel Knapp wrote, “Dexter had a way of his own, which he disdained to copy or suffer to be copied...In short, he was a living exception to all general rules, and a living contradiction to all maxims of human wisdom.”


Lord Timothy Dexter died unceremoniously and was mostly forgotten by history. Never having achieved the acceptance of the elite circles of society he had so desperately craved, as well as alienating those closest to him. He died a lonely man, known as an eccentric; a person one would rather know about than know personally, and that is what’s truly unfortunate.


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