I only do long posts if they’re good ones. This is someone I have wanted to cover for a long time (since well before my 100th post, where I first mentioned him), because he is one of the most fascinating cases of human life to have ever graced this earth. It took me a while to determine whether Timothy Dexter was a good enough name to grace the pages of this fine and esteemed blog. When I remembered that he had made a legal attempt to change his first name to Lord, I decided Lord Timothy Dexter belonged. It is with great pleasure that I share his peculiar story. – Dave

Timothy Dexter was way more eccentric than he looked.

Lord Timothy Dexter was born in 1748 as plain-old Timothy Dexter to a poor family in Malden, Massachusetts. With no formal education, he began working as a farm laborer at age 8 and later worked as a leather dresser. At 21, he moved to Newburyport, Massachusetts, where the man with an unlucky lot in life proved to be lucky in love, earning the favor of wealthy widow Elizabeth Frothingham, whom he promptly married.

Suddenly, Dexter had the trappings of great wealth, and bought a mansion with Elizabeth. However, Dexter was considered an uneducated “lackwit” by his contemporaries, and they routinely gave him bad business advice for their own amusement… but Timothy Dexter always had the last laugh. Over the next three decades, through a combination of gumption, elbow grease and extraordinary luck, Lord Timothy Dexter would become one of the greatest success stories of the early American era.

Some history: during the American Revolutionary War, the continental congress printed “Continental currency,” often in peculiar denominations like $0.167 or $80. The rebel dollars were overprinted, and depreciated to below 20% of their original value, birthing the hip phrase “Not worth a Continental.”

Apparently Dexter hadn’t heard the phrase, and as the war neared its end, purchased tons of the near-worthless currency. However, the U.S. would win the war, and upheld their promise to honor the money, allowing Dexter to amass a large fortune.

With his newfound wealth, he built two ships and entered the shipping business, becoming arguably the most peculiar success story in the history of commerce.

First, he made the odd choice to sell warming pans (used to heat bedsheets in cold New England) to the hot, tropical West Indies. Upon arriving, his captain sold them as ladles for the booming molasses industry and made a handsome profit. Dexter then sent wool mittens to the region, and his ship ran into a group of Asian merchants who exported them to Siberia.

But the string of odd luck would continue. Socialites jokingly told him to ship coal to England’s coal mining capital of Newcastle.

The idea was so preposterous it had become a synonym for “bad business idea” 100 years earlier. But nobody told that to Timothy Dexter… the ship arrived in the midst of a coal miners strike, and Dexter profited handsomely.

Then things became really interesting, as Dexter carried out an astounding string of odd successes. He sold Bibles to the East Indies, where missionaries happened to have a shortage of them. He sent stray cats to the Caribbean Islands, where locals welcomed a solution to rat infestation. Tricked into sending gloves to the warm South Sea Islands, along the way his crew met a Portuguese ship looking for additional cargo to send to China, and Dexter again made off like a bandit. He also mistakenly hoarded large amounts of whalebone, but later had success selling it as a support material for corsets.

Now one of the wealthiest people in Massachusetts, his upper class peers refused to socialize with him, as they considered him plebeian and hoi polloi, and were disapproving of his ostentatiously large hats. His interpersonal relationships were suspect as well:

Despite being the cause of his fortune, Dexter considered his wife to be a nag, and for well over a decade, he told visitors that his wife had died, and that the “drunken, nagging woman” they saw caring for his kids and walking about town was actually his dead wife’s ghost. In truth, she was very much alive.

In twelve straight municipal elections, he sought to run for office, but each time was given the position of “Informer of Deer,” whatever that means. He then bought an estate in Chester, New Hampshire, and upgraded his already-large primary residence by buying an enormous house in Newburyport. He then took on a Cavendish-ian building project, decorating his enormous estate with Mosque-inspired

“Lord” Timothy Dexter’s house, fit for “the gratest felosofer in the Western world”.

minarets, a giant golden eagle statue, and a luxurious tomb where he would be placed after death. He also commissioned 40 hand-carved statues of famous men like Napoleon Bonaparte, William Pitt, George Washington and Thomas Jefferson to be displayed on his property. He also had them make one of himself, with the inscription “I am the first in the East, the first in the West, and the greatest philosopher in the Western World.”

Now one of the richest men in the colonies, Dexter took to calling himself Lord Timothy Dexter (very much out of tune with the spirit of early American collective individualism). He also made his wife and son adopt Lord as their middle name, but let his daughter’s name stay as-is. Though the wealthy still disdained Dexter, he gained respect from the many lower- and middle-class people he helped employ.

However, Lord Timothy Dexter’s greatest accomplishment was yet to come.

Seeking to make an impact in the literary world, Dexter penned his definitive work A Pickle for The Knowing Ones or Plain Truth in a Homespun Dress. In it, he wrote about his life and ranted about the clergy, politicians, and his nagging wife. But remember, Dexter had never learned to read or write, so the 8,000-word, 33,000-letter book featured frequent misspellings, random capitalization, and no punctuation marks. Inside, the book had such “foude fer thort” as:

“Now to shoue my Love to my father and grate Caricters I will shoue the world one of the grate Wonders of the world in 15 months if now man mourders me in Dors or out Dors such A mouserum on Earth” – Lord Timothy Dexter, A Pickle for the Knowing Ones

In case you were wondering, that sentence was about honoring the greatest people in history (including Dexter himself) in a museum that would become one of the great wonders of the world. The complete book (or holl pickle) has been preserved here, along with a Split Pickle version in which the original text is shown next to a version translated into proper English.

The book was originally printed to give out for free, but it wouldn’t be a Lord Timothy Dexter story if he didn’t become exorbitantly wealthy in spite of his bizarre mental faculties and eccentric Midas touch, now would it?

A Google Image search for “A Pickle for The Knowing Ones” brings up this image. Seems oddly appropriate.

Instead, the book was a smashing success, and was reprinted and sold in 8 subsequent editions! For the second edition, Dexter responded to literary critics by adding punctuation. Not normal punctuation, mind you. Instead, he kept the original text, and added thirteen pages of pure punctuation marks, instructing readers to “peper and solt it as they plese.”

His life’s work finally complete, Dexter decided to announce his own death, and held a mock wake attended by 3,000 people. The attendees were likely displeased when, during the ceremony, they heard Dexter (still alive) screaming at his wife for not grieving sufficiently.

A few years later, in 1806, Dexter would pass away for real, and with that, America lost a peculiar, totally off-the-rails, yet surprisingly brilliant mind. Unfortunately, Dexter was not buried in the luxurious mausoleum he built for himself under the “Tempel of Reason,” but rather in a family plot on Old Hill Burying Ground. However, his wishes to be buried under the “houl Lite” of a full moon were upheld, and his epitaph “Lite comes from the East” continues to shine upon future generations.