AMAZING LIVES: Timothy Dexter

“Selling coal to Newcastle” (or variations, like the alliterative “carrying coal to Newcastle” or the less popular “taking coal to Newcastle”) is a British idiom for a pointless or foolish action. The city of Newcastle upon Tyne was the home of Britain’s coal industry for at least 150 years, so taking coal there to sell would be silly. I’m not sure there’s an exact analogue for it in American English, but the old saying “he could sell ice to Eskimos” shows a similar ironic humor.

But there was once a man who did sell coal to Newcastle. And his name was Timothy Dexter.

Dexter was born in Malden, Massachusetts on January 22, 1748. His family would probably be considered poor by modern standards, but was a typical farming family of the day that didn’t have a lot of material wealth. Timothy therefore stopped attending school at age 8 and, barely literate, started working on the family farm. At 16 he was apprenticed to a leathermaker. At some point thereafter, he moved to Newburyport, Massachusetts to open his own leather business. The historical record is silent on whether Timothy’s business was a success, but somehow or the other was soon able to convince a rich widow named Elizabeth Frothingham to marry him.

Dexter was nothing if not ambitious, and frequently petitioned the Newburyport council for some sort of job that might improve his station. Remember, Dexter was barely literate: not only was his spelling awful (even by the loose standards of the time), his penmanship was said to be truly terrible. It’s likely that the Newburyport council only read the first or second petitions, then tossed all subsequent petitions into a pile. But they could only ignore him for so long: the pile of Dexter’s petitions eventually got so tall that the council, perhaps sarcastically, resurrected the ancient title of “Informer of Deer” – a job not filled since the early days of the Massachusetts Colony, when the line between eating and starving was so thin that it was considered a good idea to have a person whose full-time job was to go out and look for deer. So, Timothy Dexter: Informer of Deer.

Local “society” types in Newburyport took an instant dislike to him. I don’t know if this was strictly because of Dexter’s lower-class background, his lack of formal education, his “eccentric” personality or what. But many of Newburyport’s moneyed men purposely gave him bad business advice, in hopes of making him go broke. Unfortunately for them, Timothy Dexter seemed to have the world’s longest streak of good luck.

Towards the end of the Revolutionary War, the society types convinced Dexter to buy up as much Continental Currency as he could. During the conflict, Congress issued a staggering $241,552,780 worth of the money, which is only slightly less than the combined spending of the entire US government from 1789 to 1814 ($249,687,000), which includes most of the spending for the War of 1812.

Issuing all that fiat money was bad enough, but since the Continental Congress couldn’t force monetary policy on the various colonies, they too issued their own notes. And the British also engaged in a massive counterfeiting operation against the Continental, so the money rapidly lost value. In less than three years, the notes were trading at just 1/5 their printed value. Two years later, they were being traded at 1/40 their printed value. So worthless they became that by May 1781, Continentals ceased being used as currency at all. As you might remember from history class, the phrase “not worth a Continental” thus entered American English as a disparaging term for something worthless.

Some folks bought huge quantities of the worthless currency, as well as bonds issued by the Continental Congress or one of the colonial governments, often for pennies on the dollar. After the war and the failure of the Articles of Confederation, the new United States government faced a huge question: should they take the easy way out by simply declaring the old currency and bonds worthless? Or should they do the right thing and honor their financial obligations?

Many wanted to take the easy way out, not just because it was easy, but because it also seemed fair. As soon as news of the plan leaked, speculators in New York City (then the US capital) fanned out across the country like a plague of locusts, buying up as much Continental paper as they could get their hands on. People like James Madison thought it was completely unfair for city slickers from New York to make a mint off the deal while the common soldiers and civilians who had given their all for their country would get nothing. So Madison proposed a complex plan in which current holders of Continental paper would receive market value for the paper, but original holders would receive market value plus the difference between face value and market value.

Alexander Hamilton wasn’t insensitive to Madison’s concerns, but was (rightfully) worried that if the US government simply said “nah, we’re not gonna pay that”, the fledgling country would have massive problems borrowing money in the future. Plus, Hamilton thought, Madison’s plan was simply unworkable. In most cases it was impossible to determine who had originally owned either currency or bonds, and thus Madison’s plan was guaranteed to introduce much more fraud into the system than mere speculation alone.

Hamilton’s side ended up winning the argument: in 1790 it was announced that Continentals could be exchanged for new treasury bonds at 1% of face value. This might not sound like much – it effectively said that every Continental dollar could be traded for a penny – but it was enough to make many speculators rich… Timothy Dexter included. He became so rich that he even gave himself his own nickname: “Lord”. I can imagine the expression on Lord Dexter’s face when he’d bump into the “friends” who’d tried to cheat him:


Dexter’s story would be pretty good if it ended there. But it doesn’t. He’d also purchased a considerable sum of European currency, and once trading resumed after the war the “worthless” British pounds and French francs were suddenly worth a lot. Dexter made even more money, and he used the largess to buy two merchant ships.

One of the jealous rich folks suggested to Dexter that warming pans – basically an iron bowl with a locking lid and long handle, into which coals or embers were placed, for heating cold New England beds on winter nights – would be a good item to sell in the Caribbean. So Dexter bought a ship’s worth of them and sent them down to the islands on one of his boats. The captain of the ship, a resourceful guy who apparently had Dexter’s back, knew that warming pans were useless in the Caribbean, so instead sold them to molasses plantations as ladles. Both Dexter and his captain made a nice profit. Dexter then sent an entire ship full of wool mittens to the Caribbean. And again his luck held: a group of Asian merchants just happened to be in the area, and bought the whole shipment to sell in Siberia.

But wait… it gets even better! New England’s high-society types could barely contain their laughter when news spread that Dexter had packed one of his ships full of Bibles and sent it to the East Indies and sent the other ship to the West Indies with a hold full of stray cats. Here again, Dexter’s luck held out: a large group of Christian missionaries had arrived in the East Indies just days before Dexter’s ship, and desperately sought Bibles to distribute to the natives. And rats had become such a problem for some Caribbean islands that the stray cats actually sold for a premium as rat catchers. Once again, Dexter made money off what seemed like the worst business idea ever.

A group of high society types then told Dexter he could make money by shipping gloves to the South Sea Islands… and you can guess what happened next: Dexter’s ship of gloves arrived just as some Portuguese ships were about to leave on a trading mission to China. The Portuguese bought all the gloves, and once again Timothy Dexter, like some sort of 18th century Kozmo Kramer, fell backwards into money.

You’d think at some point the high society haters would have just given up. After all, they’d tried punking Dexter, like, a dozen times, and every single time Dexter just ended up with more money than he’d had before. I don’t know exactly how it went down, but I can just picture some upper crust New Englanders sitting around someone’s parlor, and someone piping up with: “Look, we can try the ‘selling coal to Newcastle’ thing… but he can’t possibly be that stupid… can he?”

That stupid (or eccentric, or just plain charmed) Dexter was, and soon an entire ship full of coal was making its way from Massachusetts to Newcastle. The blue bloods might have giggled with glee and twirled their evil mustaches in anticipation of Dexter finally losing all his money. But that’s not how this story works. Dexter’s ship arrived in Newcastle at the height of a coal miner’s strike. Local production had ceased, and coal prices had shot through the roof! So, in this, Dexter didn’t just make money… he turned an entire idiom on its head!

Timothy Dexter House, Newburyport, MA
(click to enlarge)

Dexter had fun with his money. He bought a huge house in Newburyport (pictured above) and pimped it out with minarets, a mausoleum, a golden cupola on top, and forty wooden statues of people he considered “great men”, including William Pitt, George Washington, Thomas Jefferson, Napoleon Bonaparte, and (of course) himself. He even had I am the first in the East, the first in the West, and the greatest philosopher in the Western World carved on the pedestal holding his own statue. And if all that wasn’t enough, he also bought an estate in Chester, New Hampshire.

Dexter didn’t care much for his family. He seemed to ignore his children, but had a active distaste for his “nagging” wife. In fact, he’d usually tell visitors that his wife had died, and the “crabby” person they saw before them was actually her ghost come to haunt him.

And speaking of, Dexter once faked his own death. He was apparently obsessed with death, sleeping in his coffin for most of his later years and worrying over how many people would turn out for his funeral. So, on November 14, 1800, he had his death announced and a wake and funeral was planned. According to historical records, 3,000 people showed up for the wake, only to be disappointed when they heard Dexter screaming at his poor wife that she didn’t appear to be “grieving enough”.

At age 50, Dexter began work on the main thing that would leave his mark on history: a book titled A Pickle for the Knowing Ones or Plain Truth in a Homespun Dress. The book – available here if you can stomach it – is basically just Dexter ranting about politicians, the clergy and his wife. It contains 8,847 words made from 33,864 letters… but not a single punctuation mark. Capital letters appear, for no discernible reason, at random. Here’s an excerpt:

IME the first Lord in the younited States of A mericary Now of Newburyport it is the voise of the peopel and I cant Help it and so Let it goue Now as I must be Lord there will foller many more Lords pretty soune for it dont hurt A Cat Nor the mouse Nor the son Nor the water Nor the Eare then goue on all is Easey Now bons broaken all is well all in Love Now I be gin to Lay the corner ston and the kee ston with grat Remembrence of my father Jorge Washington the grate herow 17 sentreys past before we found so good a father to his shildren and Now gone to Rest

Dexter originally gave the book away to anyone who asked, but it proved popular enough to generate eight printed editions. An overzealous editor, complaining to Dexter about the lack of punctuation, irritated him into adding an extra page in the second edition, which consisted of 13 lines of punctuation marks, with which, said Dexter, readers could “peper and solt it as they plese”.

Lord Timothy Dexter, Informer of Deer, died for real on October 26, 1806. On April 28, 1807, most of his home furnishings were sold at auction, along with all the wooden statues. Most of these rotted away over time, but the William Pitt statue apparently still exists and is supposedly on display at the Peabody Essex Museum in Salem. On July 3, 1809, Dexter’s long-suffering wife, Elizabeth Lord Dexter, died. The house was soon sold and turned into a resort, which lasted until 1852. His home, now apartments or condos, still stands at 201 High Street, in Newburyport, Massachusetts.

3 Replies to “AMAZING LIVES: Timothy Dexter”

  1. Yes, I know. I could have used a picture of Bill Clinton giving a thumbs-up or Tom Brady celebrating a touchdown. But I chose the picture of Ducreux instead.

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