Timothy Dexter’s Curious Business Ventures

May 30, 2025

Timothy Dexter was businessman, but he had few business sense. He attempted to sell coal to Newcastle and bed warmers to the tropics. Yet, despite his seemingly strange ventures, Dexter often managed to turn a profit. Born in 1747 in Malden, Massachusetts, Dexter rose from humble beginnings to amass a considerable fortune, not through careful planning or education, but seemingly by sheer luck and outrageous confidence. What makes his story truly fascinating is not just his financial success, but the bizarre, often comical manner in which he lived and spent his fortune.


Timothy Dexter’s house in Newburyport, Massachusetts, USA. Credit: “Famous Colonial Houses” by Paul M. Hollister.

Dexter came from a poor family of Irish immigrants who had moved to the New World the century before. His formal education ended almost before it began. By the age of eight, he was working as a farmhand, and at sixteen, he began an apprenticeship with a tanner in Boston. At the age of twenty-two, Dexter married a rich widow, and with the money set up a shop selling moosehide trousers, gloves, hides, and whale blubber. But it was a highly speculative move during the American Revolutionary War that made his fortune. Dexter began buying large quantities of depreciated Continental currency, worth little at the time, believing it might one day regain value. Against all odds, his gamble paid off when the fledgling US government honoured the notes after the war. Virtually overnight, Dexter became a wealthy man.

Timothy Dexter as a Businessman

Wealth only emboldened Dexter’s eccentric instincts. With no formal training in trade or economics, he made investments that would have seemed ludicrous to any experienced merchant, but somehow, they worked. He once shipped warming pans to the Caribbean, a tropical region with no need for them. However, locals repurposed them as molasses ladles, and the shipment sold out. He sent coal to Newcastle, England—a city synonymous with coal production—at precisely the moment the miners were on strike, and again made a profit. He even shipped stray cats to the Caribbean to help control a rat infestation, and gloves to Polynesia, where Portuguese traders bought them on their way to China.

These accidental successes turned Dexter into a folk hero of fortune—the man who got rich doing everything wrong. But like many wealthy people, Dexter may have wanted to bend the truth just a bit about how he made his money.


Timothy Dexter

“Dexter was any thing but a fool,” wrote Samuel Knapp, in one of the earliest account of the man published half a century after his death. “Every thing that he undertook, worked well; not by luck, as many thought and said, but by most excellent judgment. When he bought up the government paper, he made a brilliant speculation. He was laughed at by the old fogies of that day for taking so many shares in the first chain bridge over the Merrimack; but the smile went the other way, when for the first forty years it yielded a dividend of over twenty-five cents on the dollar!”

One of Timothy Dexter’s biographer, William Cleaves Todd, believes that many of these improbable stories of selling bed warmers to the West Indies and whalebones for ladies’ corset were fiction invented by the man himself to provoke curiosity and enhance his mystique. Todd pointed out that, at the time, America actually imported bed warmers from Great Britain. If Dexter had truly shipped 42,000 of them to the West Indies, the cost would have been around $150,000, a staggering sum for the period. This amount, Todd argued, would have had to be paid in hard currency, since “bills of exchange were then but little used.” He added, “Such an importation and exportation would have required months of time, and would have made a sensation indeed.”

Todd questioned: “Is it possible, rating his intelligence very low, that, if he had attempted such a speculation, he would not have been persuaded of its folly long before he could have executed it?”

Todd also noted the impracticability of using warming pans as ladles to strain molasses because “they are poorly adapted to this, and nearly, a century ago, when sugar plantations were few in the West Indies, but a small part of 42,000 would have satisfied any such demand.”


A typical brass bed warmer that was in use in Europe around the time of Timothy Dexter. The pan would be filled with embers and placed under the covers of a bed to warm it up. Credit: Wikimedia Commons

Todd also challenged the story of Dexter selling mittens to the West Indies, only for them to be purchased at a high markup by a ship bound for the Baltic. He wrote: “It is enough to say of this that wool and labor have always been cheaper in the North of Europe than here, and there has never been a time since 1492 when mittens could have been shipped there from America at a profit. The sale of this article is limited everywhere, as the supply from lady friends usually equals every demand. If one consignment of mittens, or of any other article in which Dexter was so fortunate, could yield such a return, why did not some other Yankee, taking the hint, repeat the venture?.”

Besides, Todd noted that he could find no record of such transactions in the books of the Newburyport custom house, where Dexter resided. He concluded: “these stories which Dexter tells to those inquiring minds so anxious to learn the secret how he made his money, is that they were the creation of his own brain, a great joke worthy of Mark Twain, successfully imposed on the community — that instead of being the fool he is commonly regarded, he fooled others.”

Timothy Dexter’s Eccentricity

While the New England high society snubbed him, Dexter craved for recognition. He declared himself “Lord Timothy Dexter” and adorned his Newburyport mansion with gaudy statues of American heroes including George Washington, William Pitt, Napoleon Bonaparte, Thomas Jefferson, and one of himself. The last had the inscription, “I am the first in the East, the first in the West, and the greatest philosopher in the Western World”. Dexter also bought an estate in Chester, New Hampshire. There, Dexter recommended people to call him the Earl of Chester. He offered one quarter to children who called him Lord Chester, and dinner and drinks for adults who did so. Dexter also offered to build a magnificent hall, and give it to the town, provided that they would name it after him. He also offered to pave their principal business street, if it should be called by his name.


Timothy Dexter’s house in Newburyport with its many wooden statues of famous men, including himself. Credit: Wikimedia Commons

In one of his most infamous stunts, Dexter faked his own death just to see how people would react. He staged an elaborate funeral, inviting mourners and observing their behaviour from a hidden vantage point. When his wife failed to grieve as dramatically as he hoped, he took her to the kitchen and gave her a beating for not appearing sorry enough about his “death.”

In 1802, Dexter, persuaded by his own greatness and confident that he was equal to any undertaking, decided he must become an author, and so he wrote a book titled A Pickle for the Knowing Ones.  The book was a chaotic, punctuation-free tirade that touches on politics, religion, the clergy, and his personal grievances, particularly with his wife. Critics ridiculed its bizarre spelling and complete lack of grammatical structure. In response, Dexter published a second edition where he added a page full of punctuation, instructing readers to “peper and solt it as they plese”.

Despite—or perhaps because of—its lunacy, the book gained popularity and went through multiple reprints during Dexter’s lifetime. He had thousands of copies printed, and gave them away for free, and that alone may have done more than anything else to increase his notoriety.


The opening page of Timothy Dexter’s unreadable soliloquy.

Timothy Dexter’s Legacy

When Timothy Dexter died in 1806, his estate was valued at just $35,000 (approximately $800,000 today). This modest sum is further evidence that his wealth was greatly exaggerated, and how improbable are his claims involving large financial transactions. 

Despite his foolish displays and cravings for attention, Dexter made some very sensible bequests on his will. He provided carefully for his family and others having natural claims on him. He also left behind $2,000 to Newburyport, the income to be expended for the poor, and $2,000 for the support of the gospel, and $300 for a bell to his native town, Maiden. His request to be buried in the tomb he had constructed in his garden, however, was denied and he was buried in the city’s cemetery.

His house went to his family, but its household furniture, gilt balls, and many of the wooden statues adorning his garden were auctioned off. The remaining statues were toppled in the great storm of 1815. These ended up being burned for firewood.

The building itself changed hands multiple times and was used for various purposes, including an inn and a  boarding house at one point.

In 1988, during restoration work, workers inadvertently set the building on fire when they tried using a blow torch to burn off paint under the eaves. The house was totally gutted. Fortunately, the Society for the Preservation of New England Architecture (now known Historic New England) had the original blueprints and the house was rebuilt. The house is now privately owned.


Timothy Dexter’s reconstructed house as it stands today. Credit: Google Street View.

References:
# William Cleaves Todd. ”Timothy Dexter, known as "Lord Timothy Dexter," of Newburyport, Mass.”
# Samuel Knapp. “Life of Lord Timothy Dexter”

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