Timothy Dexter: Clown? Genius? The Greatest Businessman In History?

May 12, 2023 | Jamie Hayes

Timothy Dexter: Clown? Genius? The Greatest Businessman In History?

Timothy Dexter didn't exactly fit into high society, but he was a member nonetheless. A barely literate laborer for his entire youth, he hit the jackpot at 22: He married Elizabeth Frothingham, a rich widow. Suddenly, this farm worker had a lot of money to throw around—and throw it around he did.

Terrible Investing

Dexter became infamous for making some of the most laughable investments imaginable. After the Revolutionary War, he bought huge amounts of Continental currency—worthless now that the Americans had declared independence from Great Britain. But that was just the beginning.

Dexter used his fortune to start an export business, but he clearly didn't know much about exports, or, you know...business. His rivals, who thought he was an uncivilized rube, told him to send bed warmers to the scorching hot Caribbean as a prank. Next, they told him to ship coal to Newcastle—one of the biggest producers of coal in England.

Or Not?

But here's the thing about Thomas Dexter: He was either secretly brilliant, or insanely lucky—maybe a little of both. That Continental currency he bought? The new government made good on the notes, and Dexter made a fortune. The bed warmers in the Caribbean? Sold as ladles to the local molasses industry. Another hugely successful investment.

And the coal to Newcastle? He sent it during a miner's strike. Jackpot yet again.

Now, was Thomas Dexter secretly a genius? Not exactly. You've got to admit, he got a little lucky—but that wasn't all he had going for him. He had a knack for seeing things that his stuffy competitors undervalued, and he knew how to play up the whole "uneducated fool" so people would underestimate him. With that trifecta, Thomas Dexter, who came from nothing, became a very rich man.

It turns out, the "eccentric moneybags" identity fit Dexter like a glove.

A Solid Gold House, A Rocket Car

Timothy DexterGetty Images Timothy Dexter's garish mansion in Newburyport, Massachusetts.

Since Dexter didn't come from the upper classes, he felt no obligation to act with decorum. His manor in Newburyport was a gaudy monstrosity (pictured above), complete with 40 wooden statues and a mausoleum for...himself. He once faked his death just to see how people would react. When his poor wife didn't cry to his liking, he revealed himself and caned her.

In fact, Dexter showed a remarkable lack of gratitude for the wife who made him who he was. Visitors to their manor were in for an awkward treat if they happened upon her: He would claim that she had died, and the woman they were seeing was her ghost.


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The Greatest Philosopher In The Western World

The crown jewel of Dexter's statue collection was, of course, a statue of himself. At its base, it bore a humble inscription: "I am the first in the East, the first in the West, and the greatest philosopher in the Western World." Dexter believed it, too, and at age 50, he decided to put all of his sage wisdom into a book: A Pickle for the Knowing Ones. And by sage wisdom, I mean "complaints about his wife, local politicians...and anyone else who annoyed him."

But wait, I thought he was illiterate? Well, he did eventually learn to read and write...kind of. He reached just under 9,000 words in the book...with no punctuation. Here's a small tidbit: "Ime the first Lord in the younited States of A mercary Now of Newburyport it is the voise of the peopel and I cant Help it and so Let it goue."


The Perfect Businessman?

All the while, Dexter's more respectable contemporaries laughed at him behind his back, this fool who thought he was a brilliant businessman. But was Dexter wrong? He took advantage of opportunities that others wouldn't touch with a 10-foot pole, and it made him stinking rich. Sure, he was lucky, but here's the dirty secret: Most successful businessmen get lucky somewhere along the road.

Maybe Dexter wasn't so different from the people who looked down their noses at him. Sure, he might have looked different, sounded different, and acted different. But he had the same pile of money to sleep on as the rest of them. You tell me.

Sources: 1

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