The Ridiculous Rise of Lord Timothy Dexter: A Tale of Lucky Blunders and Accidental Brilliance

In the late 1700s, the wealthy elite of Newburyport, Massachusetts, had a problem. His name was Timothy Dexter, and he simply wouldn’t fail.

Dexter started as a humble leather dresser — quite literally working with dead animal skins. He was barely literate, had the manners of a goat, and committed the unforgivable sin of becoming rich through sheer dumb luck. After marrying a wealthy widow (who, locals whispered, was old enough to know better), Dexter found himself with money to invest and a burning desire to be accepted by high society.

The Currency Caper

When Dexter noticed the local aristocrats buying Continental currency — paper money that was rapidly becoming worthless — he decided this must be what rich people did. But where the wealthy were cautiously buying small amounts, Dexter went all in with the enthusiasm of a labrador chasing a squirrel.

“If buying worthless money is good,” he reasoned with his particular brand of logic, “then buying LOTS of worthless money must be BETTER!”

The established merchants watched in barely concealed glee as Dexter bought enormous quantities of the depreciating bills. Some even sold him their own holdings, fighting to keep straight faces as they did so. Here, surely, was the end of the upstart leather worker.

“He’s buying paper worth less than the leather he used to tan!” they chortled in their counting houses.

But then Alexander Hamilton, the first Secretary of the Treasury, enacted his debt assumption plan. Suddenly, those “worthless” Continental bills were worth something again. While most speculators had bought cautiously, Dexter’s overwhelming enthusiasm meant he now sat on a fortune.

The local aristocrats were horrified. Not only had Dexter failed to go bankrupt, he’d gotten even richer. Clearly, more dramatic measures were needed.

The Warming Pan Debacle

Determined to see Dexter fail, several merchants came up with what they thought was a foolproof plan. They knew Dexter was desperately trying to break into shipping, despite knowing nothing about international trade.

“My good man,” said one merchant, barely concealing his smirk, “have you considered the warming pan market in the West Indies?”

Dexter, who had indeed not considered this market (or any market, really), was intrigued. Warming pans — metal pans filled with hot coals to warm cold beds — were common in chilly New England. The fact that the West Indies was a tropical paradise where people were more likely to die of heat than cold seemed to escape him completely.

“Brilliant!” declared Dexter, and promptly bought every warming pan he could find.

The merchants could hardly believe their luck. They watched with undisguised joy as Dexter loaded ship after ship with warming pans, sending them off to the sweating tropics. Finally, they thought, the leather dresser would learn his place.

But Dexter’s agent in the West Indies was rather cleverer than his employer. Arriving during a massive expansion of the sugar industry, he took one look at the warming pans and had an inspiration. With their long handles and covered tops, they were perfect for scooping and transporting hot molasses.

“Presenting,” he announced to the plantation owners, “the very latest in specialized molasses ladles, direct from the factories of New England!”

The plantation owners, struggling with the dangerous work of moving hot molasses, snapped them up. Some even placed orders for more of these marvelous “ladles.”

Back in Newburyport, the merchants watched in disbelief as Dexter’s ships returned laden with profits. Once again, the man’s complete ignorance of normal business practices had somehow worked in his favour.

The Cats and the Caribbean

By 1796, Newburyport had two problems: an overwhelming number of stray cats and Timothy Dexter’s unstoppable success. The town’s elite thought they’d found a perfect solution to both.

“My dear Lord Dexter,” suggested a merchant, dripping with sarcasm, “a man of your stature should be collecting exotic pets. All the European nobility does it. Why not start with training our local cats? Surely they’d become exotic enough with proper… refinement.”

Dexter, ever eager to appear more lordly, took the bait. He began buying every stray cat in town, paying good money for each one. Soon, his mansion became a feline paradise — or nightmare, depending on whom you asked.

“The leather dresser’s finally lost his mind,” townspeople snickered, watching cats sunbathe on every surface of Dexter’s property. His wife was horrified to find cats turning their gardens into the world’s largest litter box.

But then, Dexter overheard merchants at the dock discussing a serious rat problem in the warehouses of Caribbean plantations. While most businessmen might have considered shipping rat traps or poison, Dexter looked at his cat-covered mansion and had an inspiration.

Without telling anyone his plans, he began loading his “exotic New England rat hunters” onto ships bound for the Caribbean. The townspeople thought he’d truly gone mad — until word came back that plantation owners were fighting over his cats, paying premium prices for these expert rat catchers.

“First warming pans as molasses ladles, now stray cats as exotic rat hunters,” muttered one merchant. “The man could sell snow to eskimos and somehow make a fortune doing it.”

The Monday Night Club, which had hoped to finally see Dexter fail, watched in dismay as he once again turned apparent foolishness into fortune. Not only had he solved the town’s cat problem, but he’d also established a profitable new trade route.

“Lord” Dexter Takes the Stage

By now, Timothy Dexter had accumulated enough wealth to make even his harshest critics grudgingly acknowledge his success. But money wasn’t enough — he wanted respect. And in Dexter’s peculiar mind, respect meant one thing: becoming nobility.

“If they won’t accept me as a gentleman,” he declared, “I shall become a lord!”

The fact that America had no system of nobility didn’t bother him in the slightest. He simply started calling himself “Lord Timothy Dexter” and waited for everyone else to catch up. When they didn’t, he decided to help them along by creating his own noble estate.

The Coal to Newcastle Catastrophe

It was around this time that Dexter’s critics thought they’d finally found his weakness. During a gathering of merchants, someone mentioned the English city of Newcastle, famous for its coal mines.

“My Lord Dexter,” said one merchant, laying the sarcasm on thick, “surely a man of your… wisdom… sees the opportunity in shipping coal to Newcastle?”

Any schoolchild knew the phrase “carrying coals to Newcastle” meant doing something pointlessly foolish. But Dexter, whose education had apparently skipped both schoolchildren and idioms, took this as serious advice.

“Coal to Newcastle!” he exclaimed. “Why didn’t I think of that?”

The merchants watched in delight as Dexter loaded a ship with coal. Some even helped him find “contacts” in Newcastle, barely able to contain their glee. Finally, they thought, the fool would lose everything.

But as Dexter’s ship approached Newcastle, something unexpected happened. The local coal miners had gone on strike. The city, desperate for fuel, was willing to pay premium prices for coal from anywhere. Dexter’s shipment arrived at exactly the right moment, turning what should have been a disaster into yet another triumph.

Back in Newburyport, one merchant was heard to mutter, “The man could fall into a pile of manure and come up smelling of roses.”

The Great Bible Bonanza

By the late 1780s, “Lord” Timothy Dexter had become Newburyport’s most notorious citizen. His previous successes with warming pans and cats had made him wealthy, but they’d also made him hungry for bigger ventures. When a traveling merchant mentioned in passing that Bibles were scarce in the American South, Dexter’s eyes lit up with that familiar, slightly maniacal gleam.

“Bibles, you say?” he mused, already calculating in his peculiar way. “Well, if they need Bibles, they shall have BIBLES!”

What followed was nothing short of a religious book raid. Dexter didn’t just buy a few crates of Bibles — he swept through New England like a Biblical locust, buying every single copy he could find. He visited bookshops, church suppliers, and private sellers. When those ran dry, he began approaching churches directly.

The local religious community was scandalized. Several churches had to share their remaining Bibles, passing them between services like precious relics. Some Sunday schools were forced to teach from memory.

“Imagine,” huffed one church elder, “being forced to delay baptisms because a leather worker has cornered the market on the Word of God!”

But Dexter wasn’t finished. He hired agents to scour neighboring states, offering premium prices for any Bibles they could find. His warehouse began to look like a very specific kind of library.

“First he collected cats, now he’s hoarding holy books,” observed one neighbor.

The local merchants, who had learned to dread Dexter’s successes, watched with growing unease. Surely this time he’d gone too far. What could one do with thousands of Bibles?

As it turned out, plenty. A massive religious revival was sweeping through the South, sparked by traveling preachers and camp meetings. New churches were sprouting up faster than cotton, and every one needed Bibles. When word spread that a merchant had a warehouse full of them, the orders came flooding in.

Dexter’s timing, as usual, was impossibly perfect. He sold his Bibles at a massive markup, with some specially bound editions going for ten times their original price. Southern churches, desperate for copies, paid whatever he asked.

“The Lord works in mysterious ways,” muttered one minister as he paid Dexter’s price. “Though perhaps never quite as mysteriously as this.”

The Whalebone Wonder

Timothy Dexter was fascinated by the whaling ships at Newburyport’s harbour. After his success with cats, warming pans and the Bible, he decided he should get into the whaling business, too. The only problem? He knew nothing about whaling.

“My good Lord Dexter,” one whaling captain said patiently, “you can’t just buy a whale. You need a crew, and — “

“What about those white things piled up there?” Dexter interrupted, pointing to a heap of whalebone at the dock.

“Oh, those are just whale bones. Leftovers from processing. We usually sell them cheap to corset makers and such.”

Dexter’s eyes lit up. If they were cheap, surely buying them was a good idea! Without understanding what they were used for or why, he made his signature grand declaration:

“I’ll take all of them!”

“All of what, Mr. Dexter?”

“All the whale bones. Every single one. And not just these — all the whale bones from every ship that comes in!”

The whaling companies were delighted. Here was someone willing to buy their least valuable product in bulk. Word spread quickly, and soon other whaling companies were approaching Dexter with their whale bones.

The locals watched in bewilderment as cartload after cartload of whale bones arrived at Dexter’s property. His warehouses filled up. His gardens became bone yards. The smell was tremendous.

“He’s lost his mind completely this time,” townsfolk whispered. “What could anyone want with so many whale bones?”

His wife was particularly unhappy. “First it was cats everywhere, now I can’t walk through my own garden without tripping over whale parts!”

When asked about his plans for the bones, Dexter would just shrug. Truth was, he had no idea what to do with them. He’d bought them simply because they were cheap and available.

“Perhaps,” suggested one local wit, “he’s building himself a whale to ride back to whatever planet he came from.”

But just as the townspeople were certain this would finally be Dexter’s downfall, fate intervened. Women’s fashion in Europe and America suddenly underwent a dramatic change. The new styles called for massive hoop skirts and extremely rigid corsets — all of which required large amounts of whalebone.

And who happened to own virtually every whale bone on the Eastern seaboard? Timothy Dexter, of course.

Fashion houses and corset makers found themselves desperate for his supply. The price of whalebone quadrupled, then quadrupled again. Dexter, who still wasn’t entirely sure what the bones were used for, happily sold them at whatever astronomical prices his manager suggested.

“It’s not natural,” complained one fashion merchant, paying Dexter’s exorbitant prices. “No man should have this much control over ladies’ undergarments — especially one who doesn’t even know what they’re for!”

The profits from the whalebone venture were staggering, even by Dexter’s standards. He used some of the money to build his famous mansion and populate his garden with wooden statues of famous figures — including himself, naturally.

The statue of Dexter was particularly grand, bearing a plaque with the inscription: “I am the first in the East, the first in the West, and the greatest philosopher in the Western World.” When someone pointed out that this might seem a bit presumptuous, Dexter’s response was characteristic:

“Show me another man who’s made a fortune from whale bones, and I’ll show you another philosopher!”

A Pickle for the World

Fresh from his whalebone triumph, Timothy Dexter decided it was time to share his wisdom with the world. The fact that he could barely read or write didn’t deter him in the slightest.

“All great lords write books,” he declared to his secretary. “It’s time I wrote mine!”

And so began the creation of “A Pickle for the Knowing Ones.” Dexter dictated his thoughts randomly, jumping from topic to topic like a frog in a pond. He ranted about his enemies, praised his own genius, offered bizarre political advice, and shared his views on everything from religion to proper garden maintenance.

The manuscript was a publisher’s nightmare. Dexter had his own creative approach to spelling: “ghost” became “gost,” “brain” became “brane,” and “America” transformed into “A mercary.” Punctuation was entirely absent.

Local printers refused to touch it. “This isn’t a book,” one said, “it’s an assault on the English language!”

But Dexter, as usual, wouldn’t be deterred. He paid for the printing himself and had copies distributed free across New England. To everyone’s surprise, the book became a sensation — though perhaps not for the reasons Dexter imagined.

People began holding “Pickle Parties” where they would gather and read passages aloud, competing to see who could make sense of Dexter’s prose. Taverns offered free drinks to anyone who could read a full page without laughing. The book’s popularity spread. College students began quoting it ironically.

When readers complained about the lack of punctuation, Dexter’s response was characteristically unique. The second edition included an entire page filled with nothing but punctuation marks — hundreds of commas, semicolons, periods, and exclamation points. He wrote in the new preface. “Pepper and solt those punctuations as you pleese!”

This only made the book more popular. Copies began selling for premium prices. People would invite friends over specifically to “pepper and solt” passages from Dexter’s work.

The literary establishment was horrified. One reviewer wrote: “Mr. Dexter appears to have done to the English language what he did to the whalebone market — cornered it, mangled it, and sold it back at a profit.”

The book’s most famous line became a sort of catchphrase in New England: “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.”

Even today, rare copies of “A Pickle for the Knowing Ones” sell for thousands of dollars to collectors, proving once again that Timothy Dexter could profit from absolutely anything — even his own illiteracy.

As one book collector later noted: “Dexter may not have known how to write, but he certainly knew how to make people read.”

But Dexter didn’t care. He had his fortune, his mansion, his statues, and his book. He had proven that in business, as in literature, conventional wisdom was sometimes overrated. Sometimes, all you needed was the courage to be spectacularly, monumentally wrong — and the luck to have it turn out right.

The Legacy of Lucky Lord Dexter

Timothy Dexter died in 1806, leaving behind a legacy that defied explanation. Was he a secret genius whose apparent foolishness masked a deep understanding of market forces? Or was he simply the luckiest fool who ever lived?

The merchants of Newburyport never figured out how to make him fail. Every attempt to trick him into bankruptcy somehow turned into another success story. Perhaps his greatest achievement was proving that sometimes, the best business sense is no business sense at all.

As one contemporary noted: “In Dexter’s case, Fortune not only favoured the bold — it positively doted on the dim.”