Transcript
Hey Thoughty2 here. Since the dawn of man an estimated 117 billion human beings have been born. That’s a lot of people. Stack them on top of each other and you could build a tower tall enough to reach the sun, with enough spare human bricks to make it a third of the way back home again.
About 93% of the people in this 10 light minute tall tower are already dead, and almost all of them are long forgotten. We don’t know who they were, where they lived, or what they did with the time that was given to them. But that isn’t true for everyone. In 2022 a team of scientists took on the daunting task of building a comprehensive list of what they called notable humans.
The result was a database of 2.29 million famous and influential people, spanning the entirety of recorded history. If you were to build a tower out of these guys, it would barely even make it 1% of the way to the moon. To be a part of the tower on the left is easy, all you have to do is be born.
But to take your place in the tower on the right, you have to be kind of a big deal. The tower of notable humans contained world leaders, influential scientists, intrepid explorers, and revolutionary inventors. But, interestingly enough, it also contained one or two complete idiots, including the subject of today’s video.
His name was Timothy Dexter, and he may just have been the greatest idiot who ever lived. And if that sounds harsh, just allow me to explain. Timothy Dexter was, ostensibly, a businessman. But during his 59 years on earth, he made several of the worst business decisions since the guy who bought a pizza for 10,000 bitcoin in 2010.
2010. Some of the highlights from Dexter’s now infamous career include the time he almost bankrupted himself buying a currency that didn’t exist, his genius idea to ship tens of thousands of bed warmers to the Caribbean, and his ill-advised attempt to export coal to one of the biggest coal-producing cities in the world.
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how to do for yourself today. Despite having all the business acumen of Dr. Evil after 15 pints of Special Brew, Dexter’s utterly disastrous investments somehow made him unfathomably rich. The man was basically King Midas on crack, everything he touched, no matter how absurd, it turned to shiny gold.
If that’s all there was to Timothy Dexter’s story, it would still be quite a good one, but he wasn’t merely a lucky businessman, he was also as mad as a box of frogs. After getting rich, he hired a poet to literally sing his praises, he wrote what might just be the worst book ever, he paid people in food to call him Lord Dexter, he even faked his own death before appearing at the funeral to have a fight with his wife.
I could go on, but I don’t want to spoil the fun, because this is the utterly bonkers story of Timothy Dexter, a man so stupid he was kind of a genius. Timothy Dexter was born in the town of Malden, Massachusetts on the 22nd of January, 1747. Considering all the mischief he would manage later in his life, his younger years were surprisingly unremarkable.
Born to a family of early Irish immigrants, money was never an issue in the family home because the Dexters didn’t have any. Things were so tight that poor young Timothy was forced to drop out of school when he was just 8 to go and work as an indentured servant on a nearby farm.
In case you aren’t familiar with the concept of indentured servitude, it was basically just slavery with a fancy name, though the slaves were able to earn their freedom after working for a certain amount of time. For Timothy Dexter, it was 8 years, and when his contract was up, he moved into the city of Boston where he soon found a new career as an apprentice tanner.
but it paid well enough, and it was certainly a step up from being a literal slave. Dexter would spend over 15 years tanning things, before an unexpected new career opportunity came his way when a senior colleague suddenly passed away. But it wasn’t the man’s job Dexter took over, it was his wife, well, widow.
In truth, Elizabeth Frothingham wasn’t really Dexter’s type, something that will become extremely apparent very soon, but she did have one attribute that he greatly admired – she was absolutely filthy rich. Not only had Elizabeth recently inherited her wealthy husband’s estate, she was also something of a businesswoman herself, having made a tidy sum working as a hookster, a pretty impressive feat for a woman in the 18th century.
Dexter wasted no time whatsoever spending his new bride’s hard-earned cash. After moving into her house in the affluent Charlestown neighbourhood of Boston, he set up a new leather-working shop in the basement and set about turning himself into a modern gentleman. As far as Dexter was concerned, he had officially hit the big time.
His leather business was doing well, and he had more money than he could ever have dreamt of when he was a kid, but there was one small problem. Charlestown was one of the most upmarket neighbourhoods in all of America, home to future founding father John Hancock and other assorted members of American high society.
Dexter’s new neighbours were rich, well-educated, and almost all of them were born into money. As a former farm slave of understandably rough manners and limited learning, Timothy Dexter wasn’t exactly welcomed with open arms by the local community, and so he did what countless millions of new kids on the block have done before and since.
He tried his best to fit in. Dexter studied the mysterious ways of his new peers intensely.
He tried to copy them. He wore the same clothes and frequented the same establishment. He worked on their mannerisms and had a go at copying their flowery language. He even tried to emulate their business decisions.
And it was one of those that ultimately started what would one day become the legend of Timothy Dexter. The US dollar is very probably the most famous currency on earth. But this now ubiquitous medium of exchange was not in fact the first money in the USA. That honour belonged to what was called continental currency, introduced after the outbreak of the Revolutionary War in 1775.
There’s a good chance you’ve probably never heard of it, particularly if you aren’t American, and there’s a good reason for that. Because the USA’s first attempt at introducing a new currency did not go well. The ins and outs are complicated, but to oversimplify things a bit, Continental Congress printed far, far too many of their shiny new bills, and combined with widespread counterfeiting by the British, the value of the continental dollar plummeted almost immediately.
By 1778, it was worth 15% of its original value, and two years after that, just two and a half percent. By 1781, it was so worthless it stopped functioning as currency at all. For most Americans, it was a truly terrible situation. Many of the soldiers who fought in the Revolutionary War had been paid their wages in continental currency.
As its value plummeted, they were left with nothing. But their loss was Timothy Dexter’s gain. You see, as the value of the continental currency had begun to fall, several of Dexter’s hoity-toity new neighbours, including John Hancock, had decided to invest. Desperate to be one of the boys, Dexter had followed suit.
Hancock and co. probably bought the continentals more to show faith in the failing currency than as an actual
attempt to make a profit, but apparently nobody had told Dexter that, and so rather than buy a modest quantity of continental dollars like his would-be friends had done, Dexter bought them all. Every single continental dollar he could get his hands on. And he kept on buying them, even after the currency was essentially discontinued.
By some accounts, he bought somewhere in the region of 20% of all the continental dollars ever printed, and he invested almost every cent he and his wife owned to do it. It was an absolutely insane decision that should have bankrupted him, but by a stroke of incredible fortune, it somehow did exactly the opposite.
In 1789, some chap by the name of Alexander Hamilton was appointed the very first Secretary of the Treasury of the USA. Amongst his early acts in the role, he helped establish the US Mint and introduced the US dollar that we all know today. But in the early 1790s, he also threw a bone to the remaining owners of the ill-fated continental currency, decreeing that continental dollars could be exchanged for US Treasury bonds at 1% of their original face value.
For most people, that was hardly something to celebrate. Those who’d hung on to their continentals had lost 99% of their original value. But Dexter had already bought all of his continental dollars when they were quite literally worthless. People had been falling over themselves to sell them to him for whatever he would pay, which was far, far less than 1% of their original value.
As a result, Hamilton’s unexpected decision made Timothy Dexter an incredibly rich man overnight.
was sorely mistaken. If anything, his money made him even more unpopular. Realising this was a fight he wasn’t going to win, he left Charlestown for good, travelling around for a bit before settling in the coastal town of Newburyport. He wrote a letter to the local authorities recommending himself for some kind of important position.
Unfortunately, there was a bit of a problem with his application. Nobody could read it. Since Dexter had been forced to drop out of school at the tender age of 8, he was borderline illiterate. When the authorities finally figured out what the hell Dexter actually wanted, his application was promptly denied.
After all, as a tanner by trade, he had no real skills or experience suitable for a life in public office. But Dexter was undeterred. Over the following months, he wrote dozens of similar letters, some begging, some pleading, but most simply demanding. But all of them were variations on the same theme.
Timothy Dexter wanted an important position in the community, and he wasn’t going to stop writing letters until he got one. Dexter’s dedication eventually paid off, though since there were no suitable positions available at the time, a new one had to be created just for him. He was named Newburyport’s first official Informer of Deer.
If you’re wondering what exactly an Informer of Deer does, well, honestly, I have no idea. It’s something to do with deer. Which is actually pretty interesting, because it turned out there hadn’t been any deer sightings in Newburyport for almost 20 years. Still, it did stop him from writing those letters.
Dexter’s fine standing in the community, now officially secured, he once again turned his attention back to the serious business of making shedloads of cash from various harebrained schemes. And here’s where his lucky streak starts to look borderline supernatural.
In Dexter’s day, selling coal to Newcastle was a popular idiom used to describe a pointless act. Back then, Newcastle was a mining town whose entire economy was based on the coal industry, hence selling coal to Newcastle was a waste of time. But apparently idioms were a bit beyond our man Dexter, because having heard so many people mentioning the idea of selling coal to Newcastle, he came to the conclusion it must be a pretty good idea.
By this point, he was wealthy enough to have bought himself a small fleet of merchant vessels, so he filled one of them with coal and sold it to Newcastle. It should have been a disaster, but this was Timothy Dexter, and so his ship just happened to arrive at the mouth of the River Tyne where Newcastle was in the midst of a crippling miners’ strike.
With nobody working the mines, the price of coal temporarily skyrocketed and Dexter made a huge profit on his batshit insane investment. So Dexter had secured himself an important place in a local community, sort of, and despite his best efforts, he was somehow getting richer by the month. But as had been the case in Charlestown, far from being accepted as an upstanding member of the community, for the most part he was met with outright ridicule.
One of Dexter’s new acquaintances even went so far as to give him deliberately terrible business advice in an attempt to ruin him, suggesting that Dexter should try exporting bed warmers to the West Indies. As a resident of New England in a time before central heating, bed warmers were a vital part of winter life for Timothy Dexter, so the idea of bringing them to a new market seemed like a good one.
Dexter had never travelled much beyond his home state, and he had no idea that the residents of the tropical West Indies had no desire to make their beds even warmer than they already were. Never a man to do things by halves.
Dexter shipped more than 40,000 utterly useless bed warmers to various ports across the Caribbean. Unsurprisingly, the locals had no interest in buying expensive items to warm their beds, but they were interested in purchasing large lidded ladles to use in the production of molasses, a huge industry in the Caribbean at the time.
Dexter sold all 40,000 bed warmers at a profit of over 70%. Many more ill-advised schemes followed over the years and, against all odds, they just kept paying off. One time he accidentally bought almost 350 tonnes of whale bone after misunderstanding a request from the captain of his fleet. In case you aren’t familiar with whale bone, somewhat confusingly, it isn’t actually made of whale bones.
It’s a strong, flexible material made from keratin that some whales use to filter small prey out of seawater. Anyway, Dexter had inadvertently bought far more of the stuff than he could ever hope to sell. That is, until a new fashion for corsets made with whale bone ribbing swept across Europe.
Having completely accidentally cornered the entire US whale bone market, he was able to sell his entire stockpile for a huge profit. Some of Dexter’s famous business deals were just as unusual, but perhaps a little less lucky. He once shipped thousands of Bibles to the Caribbean, offering them to the locals at hugely inflated prices.
Chances are they wouldn’t have sold, but he instructed his sailors to discreetly spread the word that anyone who didn’t own a Bible was very likely to burn in the fiery pits of hell. Unsurprisingly, he sold a lot, doubling his money in the process. Dexter’s adopted hometown of Newburyport may not have had any deer for him to inform on, but one animal it had in abundance was the humble cat.
In fact, there were so many stray cats that a town meeting was held to make sure they were all safe.
to try and figure out what to do with them. Dexter solved the problem by offering a small fee to anyone who bought him one of the strays and soon enough, he had hundreds of them. As to what he planned to do with them all, well, as you may have noticed, many of Dexter’s dodgy deals took place in the Caribbean.
It was a part of the world he was getting to know pretty well by now, and one thing he’d learned was that many warehouses across the archipelago were suffering from rat infestations, so Dexter shipped his mini menagerie of cats across to the Caribbean, marketing them as expert mouses.
You guessed it, he sold the lot for a tidy profit. By this point, Dexter’s business deals, both good and bad, had made him an incredibly wealthy man. But there’s no point being filthy rich if you can’t rub your neighbor’s faces in it, and so he built himself a huge and extravagant mansion, the biggest and grandest in all of Newburyport.
Fittingly, his new residence was absurdly flamboyant, complete with a columned entrance and several minarets. To top things off, he commissioned 40 full-sized wooden statues of history’s greatest men and dotted them around the garden. Amongst them were the likes of Napoleon Bonaparte, George Washington, Thomas Jefferson, and most importantly of all, Timothy Dexter himself.
Each of the statues came with a small description of the man it depicted, many containing obvious historical inaccuracies, but it was a plaque under Dexter’s own statue that was perhaps the most misleading. It read, I am the first in the East, the first in the West, and the greatest philosopher in the Western world.
Wow, I think maybe all of that money might have gotten to his head, no? Because the only thing growing faster than Dexter’s bank balance was his ego. He started styling himself as Lord Dexter, a title he’d simply made up, to encourage people to actually use it.
use it. He let it be known that anyone who did so could expect free food and refreshment on his estate. He even hired himself a personal poet to write flattering poems about all of his grand deeds. In other words, at this point, he’d basically lost the plot.
But in stark contrast to his charmed professional life, Dexter’s personal affairs were anything but lucky. He’d married for money, but now that he’d made so much of his own, he didn’t really need his wife anymore. He started spreading the word that she was dead. If anyone happened to see her wandering about the mansion, Dexter would calmly explain that it was merely her ghost who’d taken to haunting him.
Perhaps because of his humble beginnings, Dexter was a man who was obsessed with status. It mattered so deeply to him that people should respect and admire him. But how does anyone really know what other people think of them? It’s a question most of us have asked ourselves at one point or another, but good old Dexter came up with a way to actually find out.
He faked his own death. His reason was simple. Simple and totally mental. If people mourned his passing, that meant they loved him.
He arranged for one of his clerks to spread the news of his untimely demise, then arranged a suitably grand funeral for himself, with a wake to be held on his own estate. To his delight, the event was extremely well attended, with over 3,000 people turning up to mourn, or possibly celebrate, his passing.
Dexter had hidden himself away somewhere in his mansion to see how things unfolded, and to begin with, he was very pleased. But then he noticed that his wife wasn’t even crying. So he broke his cover and set about beating her with a cane in front of his presumably extremely confused mourners.
Perhaps because of the whole fake death thing…
or maybe due to his advancing years. In later life, Dexter became increasingly fixated with his own mortality. As he entered his 50s, he decided it was high time he recorded some of his hard-won wisdom in a personal memoir. For reasons I still haven’t entirely been able to figure out, he calls this infamous volume, A Pickle for the Knowing Ones, and, I kid you not, it might just be the worst book ever written.
Dexter had come a long way since dropping out of school as a boy to work on the farm, but he was still only semi-literate. Still he didn’t let that little fact hold him back. In places, lots of them, the book is almost impossible to understand. It’s a rambling, nonsensical mismatch of wild ideas, incomprehensible rants, and cipher-like strings of random letters.
From what I can tell, the main takeaway of the tome is that Dexter believed he should be appointed Emperor of the United States. It was truly diabolically awful. And yet, like everything in Dexter’s life, somehow it was a roaring success. This abomination of American literature was still getting write-ups in storied publications like the Atlantic and the New York Times over a hundred years after Dexter’s death.
It was reprinted no fewer than eight times, and Dexter even wrote a revised second edition based on his readers’ feedback. That feedback mostly focused on the fact that Dexter had apparently forgotten to include any punctuation whatsoever in his literary masterpiece. Surprisingly enough, he was happy to put that right.
The second edition helpfully included a short appendix packed full of punctuation that Dexter welcomed his readers to add to the preceding text as they pleased.
Third luck made him both a millionaire and a madman. But it’s worth pointing out that some scholars believe history has been a little harsh on Lord Timothy Dexter. It’s absolutely true that he was a man of limited education who made some laughably poor decisions, particularly in the early years of his business career.
But by the end of that career, there’s a real argument to suggest he’d grown into a pretty savvy businessman, with a genuine talent for recognising and exploiting the hidden value in unusual commodities. Whichever way you happen to see things, there’s absolutely no debating the fact that Timothy Dexter is one of the most unusual and interesting characters in American history.
And hey, maybe it’s reassuring to know that you don’t have to be a genius to earn yourself a place in the Tower of Notable Humans. Sometimes all you need is a bit of luck. Thanks for watching.