Timothy Dexter — he’s one of the most bizarre and entertaining characters in early American history

Timothy Dexter — he’s one of the most bizarre and entertaining characters in early American history. Born in 1747 in Malden, Massachusetts, Dexter was indeed poor and uneducated—a tanner by trade who rose to unexpected and almost absurd wealth through a combination of luck, boldness, and what some would call sheer madness.

Here are some wild and true highlights of his life:

🐎 Rise to Riches

• He married a wealthy widow, which helped him start climbing the social ladder.
• Without much knowledge or guidance, he invested in Continental currency when it was practically worthless. When the U.S. government later honored it, he made a fortune.
• He bought huge amounts of goods and exported them to places seemingly at random—and somehow made money. For example, he:
  • Sent bed warmers to the Caribbean (people used them as molasses ladles).
  • Exported coal to Newcastle, England—a coal-rich area. Amazingly, a miner’s strike made this profitable.
  • Sent bibles to the East Indies, which found a hungry market via missionaries.
  • Shipped cats to the Caribbean, where they were welcomed as rat-catchers.

🤪 Eccentric Behavior

• Dexter styled himself as “Lord Timothy Dexter.” He built a mansion in Newburyport, Massachusetts, and decorated it with statues of famous people, including himself.
• He faked his own death just to see how people would react. His wife didn’t mourn him to his satisfaction, so he beat her with a cane (allegedly).
• He published a book in 1802 called “A Pickle for the Knowing Ones”, which had no punctuation, inconsistent spelling, and was mostly rambling complaints. It became strangely popular.

After complaints about the lack of punctuation, he released a second edition with an entire page of punctuation marks at the end, inviting readers to sprinkle them in wherever they pleased.

🪦 Death & Legacy

• He died in 1806, but his legend lives on as a kind of American folk antihero—a testament to the weird, unpredictable nature of capitalism and charisma.

He’s often described as a “fool who beat the system,” and there’s debate over whether he was dumb-lucky or weirdly shrewd. Either way, his life is an unforgettable mix of absurdity and success.

Here’s a direct excerpt from Timothy Dexter’s legendary book, A Pickle for the Knowing Ones. This is taken from the original edition, with all its glorious lack of punctuation and spelling:

“Ime the first Lord in the younited States of A maricca & no man dare deny it and I am now going to tell the truth of things as they is & was & be they shall not be forgot…”

Here’s another, equally chaotic passage:

“I want know how you lik me—I dont care how you lik me—I want know nothing about it I am tole that I am the best of the best I dont care what the say it is nothing to me—so they keep ther mouths shut…”

And the classic move: In the second edition, after readers complained about the complete lack of punctuation, he added this at the end:

“:::::;;;;,,,,….!!!!????”
(He instructed readers to distribute them “as they pleased.”)

His book was actually given away for free, yet it gained such a cult following that copies were hoarded and preserved, and original editions today are highly collectible.