Timothy Dexter was born in 1747 in Malden, Massachusetts. His family had emigrated from Ireland roughly a century earlier, but their hopes for a better life had produced little. Timothy received almost no education. By the age of eight, he was already working long hours as a farm laborer.
Six years of that back-breaking work drove him off the farm. He made his way to Charleston, where he secured an apprenticeship as a leather dresser. After years of training, he mastered the trade and became a fully qualified leather dresser. With the capital he had saved, he walked to the booming town of Newburyport, Massachusetts, and bought a small plot of land.
He had every intention of becoming wealthy and winning the acceptance of the upper classes. He saw his road to success in a marriage. Dexter courted Elizabeth Rottinham, the widow of one of his former masters. She was nine years older than him and already had four children, but he charmed her, and they were married.
The upper-class social circles questioned her judgment for marrying an uneducated, lower-class man. Dexter ignored their remarks. What he saw was the life he wanted within his grasp. He set up a workshop in his wife’s basement and began making leather clothing.
The business proved profitable, and he saved thousands of dollars. Around this time, the American Revolution was coming to an end. In a move that struck everyone as foolish, Dexter spent all his money on Continental currency, the near-worthless paper issued by the revolutionary government. But Congress soon decided to back the currency with goods, and its value recovered.
Dexter became a very rich man overnight. With his new wealth, he bought an extravagant house. He started a trading company, built two ships, and sent a wide array of strange goods around the world. It was this trading that made everyone question his capabilities as a businessman.
One of his first ventures involved bed warmers. In cold countries, these metal pans were a common household item. Dexter decided to ship them to the West Indies. The decision appeared ridiculous, yet the pans were used in the local molasses industry and sold for a good price.
He then rounded up as many stray cats as he could find and shipped them to the Caribbean. It was an unusual and ethically questionable venture, but it worked. Warehouse owners were plagued by mice, and they bought the cats readily. Another fortunate investment came when he bought a large quantity of whalebone, purely on a whim.
When French fashions shifted toward the use of whalebone for large corsets, his stock became valuable and he sold it for a handsome profit. Perhaps his greatest fortune came from a joke. A man tried to mock Dexter by telling him to sell coal to Newcastle. Newcastle was one of England’s key mining cities, so shipping coal there would make anyone seem an utter fool.
Dexter took the suggestion seriously and did exactly that. When his ships arrived, the miners were on strike. No coal was being produced in the city, and people were desperate. Dexter’s coal sold at a premium and earned him more money than he could easily manage.
On paper, Dexter looked like an intelligent businessman who knew a good investment from a bad one. In truth, most of his success came from sheer luck. His habits did not help his case. Every afternoon he drank, and every morning he was hungover.
He only conducted business in the mornings, because by the afternoon he was too drunk. Despite his wealth, the upper classes never accepted him. Critics described him as having disgusting deformities in his character, calling him a vain, uneducated drunk and a fool who constantly sought attention. His personality infuriated those around him.
His own wife complained about his strange business ideas and lifestyle. They stayed married, but they certainly did not get along. Things grew so bad that Dexter refused to admit that his wife was alive. He began telling people that she had passed away and that the woman living in his house was her ghost.
His two children also became unstable. His son Samuel was a drunken madman, and his daughter Nancy was an alcoholic. Weary of constant criticism and saddened that he fit into no social group, Dexter had no real friends. In 1796, at the age of forty-nine, he moved to Chester, New Hampshire, where he bought a fine estate.
With all his free time, he frequently pursued women. Most of the young ladies ignored him. After he harassed a number of them, a lawyer ambushed him and gave him a beating. Following that incident, Dexter left New Hampshire and returned to Newburyport.
He again bought a luxurious estate on whose grounds he built an outdoor museum. It contained roughly forty high-quality wooden statues of recognized figures from around the world. Among those represented were Louis XVI, Adam and Eve, and John Hancock. The museum attracted many visitors, including a number of young upper-class ladies.
Dexter tried to flirt with them, with very little success, and attempted to seduce them into bed. In 1802, with a great deal of time on his hands, he decided to write a book. He had received no quality education, and his writing skills were poor. The book was called A Pickle for the Knowing Ones.
It was twenty-four pages long and consisted mostly of criticism aimed at the clergy, politicians, and his wife. It was highly opinionated and served largely as his own defense against everyone he disliked. Perhaps the strangest feature was the complete absence of punctuation. The book also contained a great many spelling mistakes and random capital letters in the middle of sentences.
He gave the book away for free, but it became more popular than he had expected and went through eight printings. In the second edition, he added a full page of punctuation marks, telling the reader to insert them wherever necessary. A few years later, Dexter began to wonder how people would react after his death. To find out, he staged his own funeral.
To make it realistic, he bribed his family to go along with the ruse. Around three thousand people attended the mock wake. At the height of the ceremony, he revealed himself, to the shock of everyone present. He was not, however, satisfied with his wife’s behavior during the wake.
She did not grieve deeply enough and hardly cried. He beat her for it shortly afterward. On the twenty-sixth of October 1806, Timothy Dexter died at the age of fifty-nine. He had never forgotten his roots, and he set aside part of his wealth to care for the poor of Newburyport.
A man who began as a nearly illiterate farm laborer ended as one of the region’s strangest and wealthiest characters, remembered less for his fortune than for the bizarre trail of luck, scandal, and eccentricity that carried him there.