A Pickle for the Knowing Ones: The Preposterous Journey of Timothy Dexter

“I am the first in the East, the first in the West, and the greatest Philosopher in the Western World”

In colonial Newburyport, Massachusetts a garden holds dozens of carved statues of some of history’s greatest men. Conquerors and thinkers like Napoleon, Thomas Jefferson, and Alexander the Great all stand shoulder to shoulder. You will not find this inscription on their statues. Rather, it rests below a statue of the owner of the garden-- Lord Timothy Dexter.

Despite his claim, it would be hard to say that Dexter was much of a philosopher. Self-assured within his own ideas, he was a successful businessman with a fiery eccentricity and a large ego. Although fortuitous in life, history has not been kind to his legacy. Unfortunately, time has washed away these statues and more from Dexter's life. Nonetheless, the absurdity of a man like Dexter draws attention. Hence, the peculiar story of his success carries on.

A Common Man

Timothy Dexter was born in 1747 to a common and unaffluent family of the time in rural Massachusetts. In his early life, he worked hard labor and received little to no education. Despite his common upbringing, Dexter would later note that he always believed he was on a path to greatness. 

Dreams like these were rare at the time. Moving above one’s social class was unlikely. Once he finished his apprenticeship, he would use his money to buy a modest plot of land for himself. Dexter’s first of many windfalls would soon come with his marriage to a wealthy widow, Elizabeth Frothingham.

Something of a Businessman

Now endowed with newfound wealth, Dexter began to look towards the business world. Dexter’s first business decision would come after the American Revolution. The young government had paid its soldiers in a currency called Continental Dollars. Inflated to the point of worthlessness, soldiers struggled to sell off their salaries for a usable currency. Some prominent revolutionaries, like Samuel Adams, bought these salaries from soldiers. It would have acted as recognition of faith in the new government and as thanks to the veterans.

Dexter considered himself a prominent figure as well and followed in their footsteps. Except Dexter took it a step further. He would go on to spend a considerable majority of his fortune on the near hopeless currency. 

In the first of an emerging pattern that would follow Dexter throughout his life, his lack of common sense would end up working in his favor. Later that year, the US surprised everyone when they announced they would repurchase all issued continental dollars at 1% of their face value. Even at the low return, his net worth skyrocketed due to the abundance of his collection. With the newfound funds, he would buy two ships and begin his journey into trading.

The Trader

All accounts of his life have little to say about Timothy before his rise to wealth. It seems to be at this point Timothy began to act on his own whim. His eccentric personality began to reflect in his trade decisions.

For one of his great ideas, he chose to ship a boat loaded with bed warmers to the Caribbean. If you aren’t a 300-year old vampire, you likely don’t know what a bedwarmer is, but they looked like this:

They were traditionally used for heating up beds in the cold winter months of colonial New England. The Caribbean is a great deal hotter than New England. A normal person would expect bed-warmers to fail in a climate that is always warm. 

Instead, the people of the Caribbean found that they were great for stirring molasses. Dexter turned a profit once again.

At one point, a cat infestation had come to attention in Newburyport. Dexter solved this by gathering all the cats and shipping them to the Caribbean too. Coincidentally, the islanders of the Caribbean were experiencing a mouse infestation. The buyers couldn't get enough of Dexter's product.

Even a man as genius as Dexter needed advice every now and then. Unfortunately, the wealthy elite of Newburyport disliked his personality and common origins. His compatriots often told him to pursue his bad ideas. On one occasion, a fed-up aristocrat had told him to “ship coal to Newcastle.” 

This was a common idiom as Newcastle was (and still is) the largest coal exporter in the world. The idiom itself meant to do something completely unnecessary. The simplest business knowledge would tell you this was a bad idea, but the phrase went right over Dexter’s head. He
packed his ships with coal and sent them to Newcastle.

As Dexter’s ships sailed for port, the workers in the same city began a massive strike. When his ships arrived, coal production had been completely halted and he sold his coal for a huge profit. By an unprecedented stroke of luck, Dexter once again charged through common sense towards success.

An Eccentric Life

Dexter remained every bit as unusual in privacy as he was in the business world. Always the model citizen, he maintained a position in government as Newburyport’s own “Informer of Deer.” At this he worked diligently, in the end reporting a total count of zero deer.

His loving wife, unfortunately, passed away early on in their marriage. Or at least that is what Dexter would claim. Dexter’s disdain had grown so large for his wife that he would pretend she was a ghost when hosting guests, and almost completely ignored her in private. 

Despite his wild personality, he was not a man without friends. There was Madame Hooper and her chicken companion. There was also Jonathan Plummer, who primarily sold porn but also wrote poetry praising Dexter for extra cash on the side.

A Novelist

Dexter himself saw his story as one of success, and his mind of that of a genius. He decided he should immortalize his knowledge in a book, which he titled “A Pickle for the Knowing Ones.” It would have been a stretch to call Dexter fully literate. The first edition of his book was completely absent of punctuation. Spelling choices were also a liberal decision as shown in this excerpt:

To no one’s surprise, the books flew off the shelf and his writing became respectably
popular. In response to critiques, the second edition has a page of random punctuation at the end and a note that readers may “peper and solt it as they plese”.

Death and Legacy

In the end, there would be two funerals for Timothy Dexter. The first in which he faked his own death to see how his popularity stood with the people of Newburyport. This would be promptly concluded when he emerged and attacked his wife with a cane for not crying enough.

The second would be in 1806. This time, he did not interrupt his own funeral nor was it a ruse. As his children had long separated themselves from him, he would leave a considerable sum of his estate to the poor of Newburyport.

His legacy as an eccentric would live on in the town of Newburyport’s collective story. Perhaps

not the most likable or smart, his ability to defy expectations was a respectable and repeated feat accomplished by him. There was little expectation of him ever leaving a mark on the world with
his societal position at birth. Yet, Timothy Dexter undeniably managed to carve himself a memorable legacy within the annals of history.