Was He Brilliant, Lucky, or Bonkers? The Eccentric Life of Lord Timothy Dexter - Commonplace Fun Facts (2024)

In the world of eccentrics, Lord Timothy Dexter stands in a class by himself. He made several fortunes through either the keenest business instincts in history or by the wildest strokes of good luck imaginable. He was mocked for his lowbrow intellect, yet he was a successful author and self-proclaimed philosopher. More than 200 years after his death, historians are still unable to reach a consensus about the peculiar man who stood conventional wisdom on its ear.

Where shall we begin about this guy?

Born January 22, 1747, in Massachusetts, Dexter did not seem to be destined for nobility. His formal education ended at the age of 8 when he dropped out of school to work on the farm. He became a tanner’s apprentice at the age of 16. Nothing to that point suggested he would live a life of comfort, but all of that changed in 1769 when he married the wealthy widow Elizabeth Frothingham.

Many people who marry into or inherit wealth make some unwise business decisions, and it appeared that Dexter had fallen into the same trap. At the end of the Revolutionary War, he sank a significant amount of his wife’s money into Continental currency. In the course of the Revolution, Congress issued about $250 million of currency. By the time the war was over, it took $40 of Continentals to buy something that cost $1 just a few years earlier.

Dexter bought up mass amounts of currency that conventional wisdom deemed as worthless. Had it not been for a fortuitous intervention by the country’s new Secretary of the Treasury, Alexander Hamilton, this would undoubtedly be the last that we would hear about Timothy Dexter. It was Hamilton, however, who pushed for the Continental dollars to be honored at 1% of face value. While this was just a tiny amount compared to the original value, it was substantially greater than the amount Dexter had paid for his loot. He instantly multiplied his net worth and became incredibly wealthy.

Dexter thought his newfound wealth would also give him respect among society’s upper class. He was disappointed in this objective. His would-be peers looked down on a man whom they viewed as crude, uneducated, and foolhardy.

Dexter was undeterred in his pursuit of respect. He purchased a fleet of shipping vessels, the best horses money could buy, and a grand chateau with the most lavish furnishings available. He was particularly proud of the “tasteful and commodious outhouses.”

Sparing no expense, Dexter commissioned top European artists to carve a series of more than 40 giant, wooden statues on his property, each depicting a great American, including one of himself. Beneath his sculpture was the not-at-all-modest inscription, “I am the first in the East, the first in the West, and the greatest philosopher in the Western world.”

The sculptures cost him more than $80,000 — more than what he paid for the entire estate. In so doing, however, he managed to do something that caught the attention of the public. This only fed Dexter’s desire for attention.

Still eluding him, however, was the respect of the upper class. When he announced his intention to launch a strong business of international trade, his detractors were quick to send him any number of suggestions — all of them designed to introduce a measure of humility to Dexter.

One notable suggestion was that Dexter sell bed warming pans in the West Indies. Anyone familiar with the hot climate of the tropical islands would know that there would be no market whatsoever for bedwarmers. Dexter, however, was unfamiliar with the climate of the West Indies. He thought the idea was marvelous and purchased 42,000 bedwarmers — enough to fill nine ships — and sent them off.

As the ships departed, the sound of laughter could be heard from almost every direction. Surely, Dexter has just made the biggest financial blunder of the century!

Once again, fortune smiled on Timothy Dexter. Although the West Indies had no use for devices to warm their beds, it turns out that the flat iron devices were perfect for use in sugar and molasses refining. The demand was so great that Dexter was able to mark up the pans by 79%. They sold out in no time, thereby further multiplying Dexter’s wealth.

Filled with confidence from this transaction, Dexter concluded that any place that needed so many bedwarmers must be cold enough to require warm clothing. He sent another ship back to the West Indies with wool mittens. These unlikely items arrived just as a group of Asian merchants was preparing to go to Siberia. Having nowhere else to acquire warm clothing, Dexter’s mittens sold at a high premium.

Another attempt to ruin Dexter came in the form of a suggestion that he sell anthracite coal in Newcastle. Newcastle was famous for being a center of coal mining, so presumably, there would be no demand for imported coal. Again, Dexter’s ignorance prevented him from having this knowledge. He seized on the idea and sent a large shipment of coal to Newcastle. Rather than introduce Dexter to failure and instill some modesty, it only proved that luck was again on his side. The coal arrived in the midst of a massive miners’ strike. Dexter was able to sell the coal at a sizeable markup, allowing him to return from Newcastle with “one [barrel] and a half of silver.”

It seemed as if Dexter could do no wrong. Whatever he decided to sell seemed to turn into gold, matter how unusual. One such example was whalebone. On a trip to Boston, he saw an opportunity to purchase a huge amount of the stuff — 340 tons, in fact. Whalebone was used in such products as corsets, buggy whips, toys, and typewriters. Dexter had purchased so much that he effectively had a monopoly on the product. He was able to markup the price by 75%, putting an end to the latest round of scornful laughter from his detractors.

Not all of Dexter’s success can be dismissed as blind luck. He showed some savvy — and somewhat cutthroat — business strategy to sell his wares. He once bragged about purchasing Bibles at “12% under half price” or 41 cents each, then selling 21,000 of them in the West Indies by sending the word to the inhabitants that they must have one Bible in every family or risk going to hell. This venture earned him $47,000 in a matter of weeks.

Reflecting on his business success, Dexter later wrote, “I found I was very lucky in spekkelation. Spekkelators swarmed me like hell houns.”

As one can see from Dexter’s statement, he was virtually illiterate. This glaring reality was the one thing his detractors continued to throw in his face. It was a reminder to the world that Timothy Dexter was nothing more than an uneducated, uncultured man who just happened to get lucky.

He attempted to silence his critics by declaring himself to be “Lord” Timothy Dexter. Despite having no claims to English nobility, he decided the title suited him and insisted upon being addressed in this manner. It did little to address his detractors’ claims that he was still an uneducated buffoon.

There was one certain way to prove his critics wrong. Dexter decided he would emulate the greatest minds of the age and write his memoirs. The result was A Pickle for the Knowing Ones, or Plain Truths in a Homespun Dress. The book unquestionably stands apart from anything of its day. (Read a free digital copy here.)

Clearly written without the assistance of a ghostwriter or editor, the book consists of 8,847 words and is utterly devoid of punctuation. His decisions about capitalization defy understanding, and the spelling is beyond atrocious.

Take, for example, this passage: “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”.

To call his writing style “train of consciousness” is to conclude that his manner of thinking was chaotic, at best. He jumps from topic to topic, sometimes in mid-sentence, assuming, of course, that you know where a sentence begins or ends, since there are no periods or commas to be found anywhere.

One person who did not fare well in his book was his wife. Perhaps for reasons that will be described later, he had reasons to suspect that she was not genuinely in awe of him. He referred to her as “the gost [ghost] A woman I maried” and that as a result, for thirty-five years, “I have bin in hell.”

Dexter self-published the first edition in 1802 and handed out copies without charge. It became wildly popular, however, and was reprinted eight times.

Responding to complaints about the lack of punctuation, he included a page in the second edition that consisted of 11 lines of punctuation marks, along with instructions that the reader could apply them wherever needed.

With his literary accomplishments secure, Dexter turned his attention next to his overall legacy. He wanted to know what people would think about him when he was gone. What better way, he reasoned, than to listen in at his own funeral?

Dexter began by building a magnificent tomb — a massive, well-ventilated room that occupied the entire basement of a fine summer home. He then had a coffin built out of the finest mahogany available. When it was complete, Dexter slept in it for several weeks, declaring it to be quite comfortable.

With these details complete, Dexter faked his own death. He let a few people in on the secret that he was really alive. Among those insiders were his wife and two children. He then had the word sent out that the great Lord Timothy Dexter had departed this mortal coil.

With strict instructions to his family that they should “act the part,” and lead everyone in grief-stricken mourning, Dexter prepared to watch his own funeral. On the appointed day, 3,000 mourners arrived. Dexter was pleased with what he saw — with one exception. His son was “sufficiently drunk to weep without much effort,” and his daughter’s head was buried in her hands. His wife, however, was not nearly distraught enough for his tastes.

Dexter had his wife brought to the kitchen where he could rebuke her. He ended up beating her with a cane when he was convinced that she wasn’t even trying to look sad. This commotion drew the attention of some of the mourners, who entered the kitchen and looked with astonishment at the man who was supposed to be in the coffin.

Realizing that his ruse was uncovered, Dexter responded by pretending as if nothing unusual had happened and that everyone was simply gathered together for a planned social event.

Timothy Dexter’s second funeral — this one for real — was held after his death on October 26, 1806. To this day, historians are divided about whether he was blessed with brilliant business instincts or if he was simply unbelievably lucky. Few would disagree, however, that Lord Timothy Dexter was one of America’s most interesting eccentrics.