Timothy Dexter: The Insane Story of the World’s Luckiest Man
A thoroughly researched account of the life and eccentricities of Lord Timothy Dexter
The life of Timothy Dexter is the ultimate rags to riches story.
Despite his very questionable business ventures, Dexter managed to become wildly successful. He began as a poor child laborer and worked his way up to a stupid rich, mansion-owning businessman.
This article details the life and eccentricities of one of the most legendary people in human history.
Part 1: The Early Life of an Illiterate Tanning Apprentice
Our account of Timothy Dexter’s life begins on January 22nd, 1747. It was on this day that Dexter was born the son of poor farm laborers in the city of Malden, Massachusetts.¹ ²
He received little education and dropped out of school before learning how to spell. At 8 years old, Dexter began work as a farm laborer. Luckily, at the age of 16, he secured an apprenticeship in Boston, tanning animal hides to make leather.³ Tanning (or leather dressing) was a popular and profitable occupation at the time, bestowing Timothy Dexter with the skills necessary for future success.⁴
At age 21, Dexter had completed his apprenticeship and decided to stay in Boston, moving to the neighborhood of Charlestown.⁵ Charlestown was the leather dressing capital of Massachusetts, where the vast majority of the industry was concentrated.⁶ It was in this neighborhood where Dexter would begin his very own leather dressing business.
During his apprenticeship, Dexter had learned how to make “Moroccan leather.” This was a unique fashion of leather that came from the Levant. The leather tanners in Charlestown had a monopoly in the production of Moroccan leather, which was in high demand due to its use in women’s shoes.⁷
In due time, Timothy Dexter met Elizabeth Frothingham, a widow whose deceased husband had also worked in the leather dressing business and left her a considerable amount of money. The two got married and Dexter continued work as a leather dresser while Elizabeth made a decent amount of money selling a small stock of goods to people door-to-door.⁸ ⁹
By around 1786, Dexter was worth several thousands of dollars and ready to undertake various fantastical business ventures.¹⁰ ¹¹
Part 2: Timothy Dexter Gets Filthy Rich
At the beginning of the Revolutionary War, the Continental Congress created the Continental Dollar (aka “Continentals”). This was the United States’ first paper money and it was used to finance the war.
As economist Farley Grubb explains:
[U]nlike most colonial paper money, Continental Dollars were written to be an explicit contractual obligation to redeem a specific sum of specie — with such being printed on the face of the bill.¹²
When the war began in 1775, $2 million in Continentals was issued. By the end of 1779, $192 million had been issued and was in circulation. Since the Continental Congress printed such large amounts of the currency, inflation skyrocketed. The value of the Continental tanked, prices soared, people started hoarding hard money (e.g. gold and silver coins), and the economy was in shambles.
The Colonies were hurting really badly financially. So much so that Alexander Hamilton said without a loan from France, they would have to capitulate to Great Britain. France did eventually provide them with funds and they pulled through.¹³
In the aftermath of the Revolutionary War, the Continental Dollar was virtually worthless. “Not worth a Continental” was a popular phrase reflecting that fact. All of this set the stage for Timothy Dexter’s first stupidly genius business venture. As Samuel L. Knapp recounts in his Life of Lord Timothy Dexter:
The old continental money was depreciated to almost nothing, and the securities issued by the state of Massachusetts, which had for a while kept public confidence in that quarter alive, had now sunk to about two shillings and sixpence on the pound. The patriotic holders were greatly distressed; many of them, possessing nothing for seven years’ services but this trash, were forced to part with it for any thing they could get.¹⁴
Dexter saw that John Hancock (then governor of Massachusetts) and a wealthy merchant named Thomas Russell were buying up Continental Dollars at fractions of their face value. Naturally, Dexter copied them, spending his entire life savings on these worthless IOUs.¹⁵ What’s more, he probably got even better deals than them. This is because he bought the Continentals in small quantities from poor people who sold them for whatever they could get.¹⁶
Luckily for Dexter, Alexander Hamilton had his back. Hamilton was the Secretary of the Treasury at the time and decided to pay back the owners of government securities.¹⁷ This included the Continental Dollar. While the holders of Continentals were not reimbursed at the money’s full face value, they were still given a pretty decent price.¹⁸ ¹⁹
Writer John P. Marquand notes in Timothy Dexter Revisited that while some aspects of Dexter’s life may have been exaggerated, his claim that he got $47,000 from the speculation of Continental Dollars could very well have been correct.²⁰ Dexter was perhaps the biggest victor of this ordeal, as $47,000 back then is around $1.6 million in today’s currency.
Having bet big on Continentals, Dexter became rich beyond his wildest dreams.
Part 3: Dexter Moves to Newburyport and Despite All Odds, Gets Even Richer
Timothy Dexter had always wanted to be a member of the upper class. Now that he was rich, he believed he could finally join high society. He was completely rejected by the local aristocracy, so he moved to the town of Newburyport.²¹
Newburyport was, unsurprisingly, a port city. It was here that Dexter would make a good deal of his fortune. He had two ships built and began an export business.
One time, some of Timothy Dexter’s clerks decided to mess with him by convincing him to sell warming pans to the West Indies. Seeing as warming pans were used to heat up beds in places with very cold weather, a tropical area like the West Indies had no use for them. When the shipment arrived to the West Indies, the captain of the ship convinced people in the molasses industry to buy them and use them as ladles. Dexter’s mischievous clerks had failed and he turned a profit.²²
Those clerks weren’t the only ones hoping for Dexter’s financial ruin. Some other merchants in Newburyport had convinced Dexter to buy up coal and send it to Newcastle. To “carry coals to Newcastle” is a popular idiom describing a useless task, seeing as Newcastle was a coal mining town in no need of external sources of coal. As luck would have it, by the time Dexter’s shipment of coal reached Newcastle, a mining strike was underway. As a result, Newcastle had a shortage of coal and Dexter successfully sold coal to Newcastle.²³
As another example of Dexter’s amazing luck, he once bought up large amounts of whalebone due to a misunderstanding and still made a profit off them. A refitter working on his ships had asked Dexter to buy a large quantity of “stay stuff”, he reportedly said that it’s almost impossible to have too much. So Dexter went to Boston, Salem, and New York to buy up a whole lot of whalebones.²⁴ He thought that the refitter was referring to corset stays (some of which were made out of whalebone), but really he was talking about ship’s rigging. It turns out that around that time, it became fashionable in France to wear long corsets made of whalebone. So Dexter again made a huge profit, selling whalebones to the French.²⁵
In addition to selling warming pans to the West Indies, coal to Newcastle, and whalebones to the French, Dexter is purported to have made many other fanciful investments, such as:
- Sending thousands of Bibles to the West Indies with a letter that said if they didn’t have a Bible, they would go to hell. According to Dexter, he sold them all, making “one hundred per sent & [a] Littel over.”²⁶
- Solving Newburyport’s stray cat problem by offering to pay people for stray cats and promising to treat them well. After amassing a bunch of stray cats, he sent them to the Caribbean where warehouse owners happily bought them to deal with their mouse infestation.²⁷
Part 4: Dexter Spends an Exorbitant Amount of Money, Lives Lavishly
Having become an extremely successful businessman, Dexter decided it was now time to buy a mansion. Since this is Dexter we’re talking about, this would be no ordinary mansion.
The three-story mansion was built on a nine-acre plot of land.²⁸ If there was any doubt regarding Dexter’s patriotism, on top of the dome that capped off the mansion there stood a large statue of a bald eagle.²⁹
The mansion was surrounded by over 40 statues depicting prominent men. Presidents, scholars, emperors, military leaders, and even a statue of Dexter himself stood outside the house, carved from wood.³⁰ Each statute had a plaque on the bottom describing the figure above it. Dexter’s plaque read: “I am the first in the East, the first in the West and the greatest philosopher in the Western World.”³¹
The statue of Thomas Jefferson was holding a scroll meant to represent the Declaration of Independence which he penned. Despite Dexter’s insistence that Jefferson actually wrote the Constitution, the painter he hired was confident this wasn’t the case and began to paint “Declaration of Independence.” He only got as far as the first three letters before Dexter ran into his house and grabbed his pistol. He came back out and shot at the painter, again ordering him to write “Constitution.” Timothy’s bullets missed, but his message hit its target. From that day on, Jefferson firmly held the Constitution and not the Declaration of Independence.³²
There exists no complete list of all the statues surrounding Dexter’s house. Luckily for us, Dexter once published a partial list in the Newburyport Herald.
The 3 presidents, Doctor franklin, John hen Cock, and Mr Hamilton, and Rouffous King and John Jea, and 2 granedears on the top of the hous, 4 Lions below, 1 Eagel, is on Coupulow, one Lamb to lay down with one of the Lions, — One Yonnecorne, one Dogg, Addam and Eave in the garden, — one horse.³³
While the mansion’s exterior was glorious, the interior was impressive in its own right. Dexter wanted his house to be on the same level as the other prominent figures in the area. So just like John Hancock and Thomas Russell, he had expensive furniture and artwork imported from France. On top of that, he bought a bunch of costly books to be showcased in his home library.³⁴
Of course, Dexter wasn’t going to put all this work into his mansion without having people over to enjoy it. He was known to throw huge parties at the house, “[turning it] into what was essentially a brothel.”³⁵
Dexter was now a big deal, at least he thought of himself that way.
The previous year, he had spent several months in the small town of Chester, New Hampshire. The locals there jokingly called him “Lord Timothy Dexter, King of Chester.” He liked how that sounded and gladly took on the title of “Lord Timothy Dexter.” After coming back to Newburyport, he made his new title known, built the aforementioned mansion, and even hired a personal poet.³⁶
The poet’s name was Jonathan Plummer and his previous vocations included being a fishmonger, teacher, physician, and dealer of pornographic literature.³⁷ Here’s a poem written by Plummer about Dexter’s mansion:
His house is filled with sweet perfumes,
Rich furniture doth fill his rooms,
Inside and out it is adorn’d
And on the top an eagle’s form’d.³⁸
Part 5: Lord Dexter Has Familial Troubles
It was around this time that Lord Dexter’s relationship with his wife fell apart completely. There had been issues for years but now Dexter refused to even acknowledge her presence in the house they shared. He began referring to her as “the gost.”³⁹ In fact, when guests came over to his house and asked about his wife, Dexter told them she was a ghost and should be paid no attention to.⁴⁰
Timothy Dexter had two children with his wife, a son and daughter. His son, Samuel Dexter, did not do too well in school. He wasn’t very bright and the other kids didn’t like him. In fact, biographer Samuel L. Knapp had some very harsh words for him:
[Samuel Dexter] was capricious in his appetite, petulant in his temper, and cowardly in the extreme, and, in fact, rotten to the core.⁴¹
The only redeeming quality about Samuel (in his peers’ eyes) was that his father was rich. Samuel used this to his advantage. He bribed his classmates with cakes and other sugary foods so they would stop insulting him, all paid for with his father’s money of course.⁴²
When Samuel got a bit older, he convinced his father to let him take a cargo ship to Europe so he could try his hand at commerce. After arriving in Europe, he bet all the cargo on the gambling table and lost it all.
In due time, Samuel returned from Europe. Having lost all the cargo, his relationship with his father would never recover. The two were now embittered in constant arguments with each other. On top of that, Samuel ended up losing all of his own money and became an alcoholic. Knapp gracefully informs us that “a more useless or profligate young man could not be found.”⁴³ ⁴⁴
Samuel’s sister was named Nancy. Not to be outdone, Nancy’s life was similarly disastrous and her education was just as fruitless as her brother’s. Naturally, Timothy Dexter’s enormous wealth attracted many suitors for Nancy. The only problem was that they would always give up on their pursuits after meeting her and finding her very unrefined.
Nancy did eventually find a husband. The man’s name was Abraham Bishop and he was a scholar in the realm of philosophy. Timothy was very suspicious of him, suspicions that proved to be well-founded.
After having a daughter together, Bishop began physically abusing Nancy. This led her to become an alcoholic and they got a divorce. Now lacking a husband, Nancy moved back in with her father who supported her financially.⁴⁵ This bit seemed to be particularly tragic to Knapp, who wrote:
She lived for many years a sad object of fatuity and wretchedness. There are none of the creatures of God that make so pitiful a spectacle as a feeble mind sunk in vice.⁴⁶
Part 6: Dexter Fakes His Death
As if there wasn’t enough already going on in his life, Dexter decided to fake his death and have a mock funeral.
Dexter already had a tomb built in his garden and an elegant mahogany coffin. So when his ‘death’ was announced, invitations were quickly sent out for people to come to the mansion for the funeral.
Around 100–200 people showed up for said funeral. As historian John J. Currier recounts, Dexter watched the funeral procession from an upper-story window as it moved from the house to the tomb in the garden.
Towards the end of the ceremony, people heard a loud noise coming from the kitchen. To their surprise, they found Timothy Dexter hitting his wife with a cane for not crying enough at his fake funeral.⁴⁷ ⁴⁸
Part 7: The Illiterate Dexter Writes a Memoir
Despite being illiterate, Lord Timothy Dexter penned the autobiographical masterpiece titled A Pickle for the Knowing Ones. Published in 1802, this momentous work details his rise to wealth as well as complaints against priests, colleges, his wife, and the Knowing Ones.⁴⁹
The book contains absolutely no punctuation and completely random capitalization (as well as abhorrently misspelled words). Here is an excerpt from the first page:
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 them⁵⁰
Despite looking like complete gibberish, A Pickle for the Knowing Ones actually gives some insight into Dexter’s life and thoughts. Thankfully, a website dedicated to Timothy Dexter contains a translation of the book into readable English. Now Dexter’s ramblings are more clear.
Here’s an example, where Dexter explains how he made his money:
[Original in plain text, translation in bold]
How Did Dexter Make His Money ye says bying whale bone for staing for ships in grosing three houndred & 40 tons — — bort all in boston salum and all in Noue york under Cover
“How did Dexter make his money?” you say. (By) buying whale bone for staying for ships, in grossing three hundred & 40 tons — — bought all in Boston, Salem and all in New York undercover.
I Dreamed of worming pans three nites that thay would doue in the west inges I got no more than fortey two thousand — — put them in nine vessels for difrent ports that tuck good hold I cleared sevinty nine per sent the pans thay made yous of them for Coucking — — very good masser for Coukey — — blessed good in Deade missey got nise handel Now burn my fase the best thing I Ever see in borne days I found I was very luckky in spekkelation.
I Dreamed of warming pans (for) three nights: that they would do (well) in the West Indies. I got no more than forty two thousand — — put them in nine vessels (bound) for different ports. That took a good hold (and) I cleared seventy nine percent. The pans, they made use of them for cooking — — [“Very good, Masser, for Coukey — — blessed good indeed, Missy, got nice handle. No burn my face, the best thing I ever see in born days.”] I found I was very lucky in speculation.⁵¹
Dexter goes on to rebuke the Knowing Ones and their deceitful ways:
mister printers the Igrent or the Nowing wons says I ort to Doue as thay Doue to keep up Cheats or the same thing Desephons to Deseave the Igrent so wee may Cheat and Likewise have wars and plunder
Mister printers, the Ignorant or the Knowing Ones says I ought to do as they do to keep up cheats or the same thing, deceptions. To deceive the ignorant so we may cheat and likewise have wars and plunder.⁵²
Dexter complains about his wife, the ‘ghost’:
To man kind at Large I Never had the honour to be Long I meane to that onerabel mesonek Order I Noked once once twise three times & the gohst Apeared sade thou shall Not enter⁵³
TO MANKIND AT LARGE: I Never had the honor to belong to that honorable Masonic Order. I knocked once, twice, three times & the ghost appeared (and) said “thou shalt not enter.”
Now to all onnest men to pittey me that I have bin in hell : 35 years in this world with the gost A woman I maried and have two Children Now Liveing⁵⁴
NOW TO ALL HONEST MEN, to pity me that I have been in hell 35 years, in this world, with the ghost — — A woman I married, and have two children, now living.⁵⁵
Dexter decides he should be emperor of America:
I Recommend pease A Congress in france and when wee are Ripe for A Emper in this Contrey Call for me to take the helm⁵⁶
I recommend Peace — — A congress in France — — and when we are ripe for an Emperor in this country call for me to take the helm⁵⁷
When A Pickle for the Knowing Ones came out, people complained about its lack of punctuation. Dexter responded in the second edition by adding a page at the end full of punctuation, telling the Knowing Ones that they may add it where they please.⁵⁸
Part 8: Dexter Dies, But Stills Lives On
Lord Timothy Dexter died on October 23rd, 1806.⁵⁹ Although he left this world over 200 years ago, the legend of Timothy Dexter lives on.
I will leave you with a quote from Samuel L. Knapp, author of the biography Life of Lord Timothy Dexter:
Such a man’s motive, it is frequently difficult to discover, and perhaps would be equally difficult for him to honestly avow. There are but few men who are sufficiently attentive to their own thoughts to be able to analyze every motive to action. Among these, Dexter was not one.
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If you would like to read a postscript with additional little-known facts about Timothy Dexter, check out the longer version of this article here.