The Idiot Millionaire

There have been aplenty words said about great men and lords. There have been a plethora of words said about wise men and philosophers. Timothy Dexter can’t be described by any of these words. Dexter’s case was a curious one. He was an 18th-century entrepreneur who made consistent ill-advised investments and was handsomely rewarded for each of them.

While he emerged successful in his business endeavors, he couldn’t breach the social elite circles of Boston. To put it in his own words, he was a “Classic Progressive ‘Libperel’” and overlooking the spelling, he was a published author and self-proclaimed philosopher.

Even though his beginnings were humble, Timothy Dexter was an ambitious man. He was born in 1748, miles away from Boston, to a family of farm laborers. During the era of British colonialism, his family didn’t see much financial stability. Despite these odds, Dexter believed he was to be a ‘grat’ (great) man. Among other labels, he was also a craftsman.

By the age of 16, he secured himself an apprenticeship with a Boston leather dresser and began his journey as a craftsman. At 21, he had finished his role as an apprentice and delved into the business of producing leather gloves and moosehide breeches. However, his situation deteriorated when the British imposed ‘taxation without representation’ which consequently resulted in the Boston Tea Party and the subsequent closing of the city’s ports after that.

Yet, Timothy Dexter chose to stay local. With nothing but a bundle of clothes on his back, he moved to Charlestown, Boston’s leather capital. It was here that Dexter’s tides began to change. He met the wealthy and recent widow of one of his former leather associates, Elizabeth Frothingham. She was an industrious and penny-pinching woman who had made an unignorable profit by selling goods door-to-door. Dexter dug his way into her frugal heart and married her.

After his marriage, Timothy Dexter was a misfit in his new neighborhood and among his neighbors. He was now in close proximity with men of significance, including John Hancock, the then Governor of Commonwealth, and Thomas Russel, the then richest man in the country. As an uneducated, boorish individual, he was naturally considered as an unequal neighbor. For obvious reasons, this infuriated Dexter.

Trying to walk in the footsteps of his gentlemen neighbors, Dexter secured a seat in the public office. To the extent of what a man who stopped schooling at the age of eight could do, Dexter flooded the neighboring Malden, MA governing body with petitions. Wearing them down, they agreed to create a post for him: Informer of Deer. His job was to keep a track of the fawn’s populations. Of course, the last deer had run off into the forest of Malden 19 years prior to that.

Satisfied with his position in public office, Timothy Dexter had now set out to earn more money and true to his nature, he found an odd way to do so. At the onset of the Revolutionary War, the Continental Congress issued America’s first form of paper currency. The soldiers were paid in Continental Dollars. It’s value ranged from ¹/₆th of a dollar to 80 dollars. During the war, the value of the currency plummeted.

Though Congress issued 250 million dollars worth of bills, shopkeepers and other locals refused to accept it, despite beaucoup efforts by Congress to punish the deniers of the currency. In reality, the Continental Dollar was now worth nothing. As a result of which the soldiers who fought in the war were now destitute.

In an effort to keep morale up, Hancock and Russel, Dexter’s neighbors started buying back the Continental Dollar. In his element, Timothy Dexter decided to imitate them to an extreme. In an idiotically brave move, he bought boatloads of the currency for fractions of pennies on the dollar. He was practically gambling his entire livelihood on pieces of paper.

But as fate would have it, in 1790 the United States Constitution validated the Continental Currency to be traded in for 1% of its face value. While this may not seem like much, Dexter had bought oodles of this currency. Hence, making him instantly and astronomically wealthy.

Even as his new wealth kept pouring in, Dexter still couldn’t gain credibility in his social circles. His efforts to penetrate the social circles were often seen as crude where it seemed like he had his foot in his mouth. He was known to speak the most inappropriate words at the most unfortunate moments.

Dexter paid no heed to his neighbors anymore. He was exhausted by his neighbor’s refusal to let him join the club. He gathered his wife and children and moved to Newburyport, Massachusetts, the most idyllic town where no matter how rich or poor, how odd or humble, all were welcome. Unquestionably, Timothy Dexter would fit in perfectly here.

Dexter decided to build his palace in this humble, accepting neighborhood. His princely abode consisted of the most lavish furnishings in the market. He hired tasteful architects from Europe and continued to erect 40 giant, wooden statues of great characters from American lore, with his statue in the middle. Beneath his statue, the inscription read, “I am the first in the East, the first in the West, and the greatest philosopher in the Western world.”

The once accepting neighborhood of Newburyport had turned on Dexter and kept devising plans for him to lose his wealth and move away. His neighbors would suggest absurd investments to him which Dexter would sincerely follow up on.

When his neighbors suggested Dexter to send out bed warming pans to the Caribbean, he obliged and sent 40,000 of them. In the hot, tropical weather of the Caribbean, these pans were obsolete. However, the people noticed these pans were perfect to mix the large containers of molasses, and thus, Dexter’s harebrained investment had paid off.

Similarly, when Dexter’s neighbors suggested he sell coal to Newcastle, the location with the largest coal mine at the time. Dexter did his due diligence and when he arrived in Newcastle, the coal miners were miraculously on strike, proving another one of his investments fruitful.

Besides his odd business sense, Timothy Dexter was eccentric. Tired of his wife’s constant nagging, he would often tell his guests at home that he wasn’t married and was simply haunted by an old lady.

In another instance of madness, Dexter staged his own funeral. He was curious to know how his loved ones would grieve and how many people would show up at his funeral. Surprisingly, 3000 people attended his funeral. However, when he felt like his wife wasn’t grieving enough, he jumped from the casket and proceeded to hit Frothingham over the head with an umbrella. While his wife eventually moved out of his home, his children moved in with him. His two sons are often described as ‘the drunk one’ and ‘the drunker one’.

With his unconventional family on one side, Dexter kept his unconventional friends on the other. Like the King of England, Dexter hired his own poet. The hapless 20 year old would write poems for Dexter and crowned him with parsley. When even the poems could not satisfy Dexter’s need for adoration and adulation, he had all his guards and servants call him ‘Lord’. He was now, ‘Lord Timothy Dexter.’

Still unsatisfied with his royal titles, Dexter dreamt of being immortal. While his method to seek immortality was sane, his execution was yet again, a spectacle. He published his memoir, “A Pickle For The Knowing Ones” complete with atrocious spelling and devoid of any punctuation. When his editor pointed out these errors to the Lord, Dexter decided to write another book. He dedicated one entire page of the book solely to punctuation marks and no words in between them.

A few years after publishing his books, Lord Timothy Dexter passed away peacefully in his sleep, in reality, this time on October 26, 1806. In a final act by society to omit all traces of Dexter from history, the Newbury Board of Health rejected his plea to be buried in the tomb he made years prior claiming it was ‘unsanitary’. He was buried in a quaint ceremony in the hills.

While his efforts to be adored and respected could be described as acts of insanity and absurdity, Lord Timothy Dexter has been described as a genius by many as well.

He was an idiot millionaire who walked blindly into the forests with nothing but a sheer cloak of luck on his back.