Timothy Dexter on a ship deck, wearing nobleman's outfit, surrounded by crates.

Timothy Dexter: The Eccentric Merchant Who Stumbled Into Fortune

Timothy Dexter, born in 1747 in Malden, Massachusetts, is one of the most eccentric figures of late 18th-century America. His life unfolded like a surreal tale of improbable success and outlandish behavior.

Despite his lack of formal education and business acumen, Timothy Dexter amassed a considerable fortune through a series of seemingly nonsensical ventures that defied conventional wisdom.

His improbable investments and personal eccentricities earned him the moniker “the lucky fool” among his contemporaries, leaving an indelible mark on New England’s cultural landscape.

The Astonishing Life of Timothy Dexter

Early Years and Rise to Wealth

Timothy Dexter was born on January 22, 1747, in Malden, Massachusetts. He came from a modest background and received minimal formal education, leaving school at the tender age of eight. As a young man, he apprenticed as a leather dresser, learning the trade of preparing animal hides.

Dexter’s fortunes began to change when he married Elizabeth Frothingham, a wealthy widow. This union provided him with the capital to embark on his unconventional business ventures.

Fortuitous Endeavors and Financial Success

Dexter’s path to wealth was paved with seemingly ill-advised investments that inexplicably turned profitable. He acquired depreciated Continental currency at rock-bottom prices, which later skyrocketed in value when Alexander Hamilton’s financial plan was implemented.

His most famous ventures included:

  • Sending coal to Newcastle, England – a city renowned for its coal industry. His shipment arrived during a miners’ strike, resulting in an unexpected windfall.
  • Shipping wool mittens to the West Indies, where they were repurposed as exotic items.
  • Exporting warming pans to the tropics, which were creatively used as molasses ladles.
  • Sending stray cats to Caribbean islands, where they were valued for pest control.

These improbably successful investments cemented Dexter’s reputation as an eccentric yet prosperous businessman.

A Colorful Character among Contemporaries

Dexter styled himself as “Lord Timothy Dexter” and surrounded himself with lavish trappings of nobility. His Newburyport mansion was adorned with numerous statues, including one of himself bearing the inscription “I am the first in the East, the first in the West, and the greatest philosopher in the Western World.”

Perhaps his most outrageous act was staging his own funeral. Dexter organized an elaborate ceremony, complete with refreshments and a coffin. He observed the proceedings from a hidden vantage point, only to berate his wife for not appearing sufficiently grief-stricken.

Literary Pursuits and Philosophical Quirks

A Pickle for the Knowing Ones

Timothy Dexter’s magnum opus, A Pickle for the Knowing Ones, published in 1802, stands as a testament to his unconventional approach to literature. This curious work lacked proper punctuation and was rife with spelling errors, reflecting his limited formal education.

The book’s content ranged from personal anecdotes to bizarre philosophical musings. In a stroke of audacious humor, Dexter included an entire page of punctuation marks in the second edition, inviting readers to “peper and solt it as they plese.”

Unique Philosophical Views

Dexter’s self-proclaimed title as “the greatest philosopher in the Western World” belied his unconventional ideas. He believed himself to be divinely inspired and often made grandiose claims about his intellectual prowess.

His philosophical views were a mishmash of half-understood concepts and personal interpretations of the world, touching on topics ranging from politics to religion, often in a disjointed and confusing manner.

Legacy and Lasting Impressions

Dexter’s unique place in history was cemented when he was dubbed “the strangest man” in an 1801 political primer. This moniker aptly captures the lasting impression of his literary and philosophical endeavors.

Today, Dexter is remembered as an embodiment of the American rags-to-riches story, albeit with a decidedly quirky twist. His writings continue to be studied as examples of outsider literature and early American eccentricity.