Dexter was born in Malden in the Province of Massachusetts Bay. He had little schooling and dropped out of school to work as a farm laborer at the extremely young age of 8. When he was 16, he became an apprentice to a leather-dresser. In 1769, he moved to Newburyport, Massachusetts. He married 32 year old Elizabeth Frothingham, a rich widow, and bought a mansion. Some of his social contemporaries considered him unintelligent; his obituary considered "... his intellectual endowments not being of the most exalted stamp,... At the end of the American Revolutionary War, he bought large amounts of depreciated Continental currency that was worthless at the time. After the war was over, the U.S. government made good on its notes at 1 percent of face value, while Massachusetts paid its own notes at par. By the time trade connections resumed, he had amassed a fortune. He built two ships and began an export business to the West Indies and to Europe. Because he was largely uneducated, his business sense was considered peculiar. He was advised to send warming pans for sale to the West Indies, a tropical area. This advice was a deliberate ploy by other businessmen to get him bankrupted. His captain sold them as ladles for the local molasses industry and made a good profit. Next, Dexter sent wool mittens to the same place, where Asian merchants bought them for export to Siberia. People jokingly told him to "ship coal to Newcastle". He did so during a miners' strike at the time, and his cargo was sold at a premium. At another time, practical jokers told him he could make money shipping gloves to the South Sea Islands. His ships arrived there in time to sell the gloves to Portuguese boats on their way to China. He exported Bibles to the East Indies and stray cats to Caribbean islands and again made a profit; Eastern missionaries were in need of the Bibles and the Caribbean welcomed a solution to rat infestation. He also hoarded whalebone by mistake, but ended up selling them profitably as a support material for corsets. Members of the New Englandhigh society rarely socialized with him. Dexter decided to buy a huge house in Newburyport from Nathaniel Tracy, a local socialite, and tried to emulate them. His relationships with his wife, daughter, and son also suffered. This became evident when he started telling visitors that his wife had died and that the woman who frequented the building was simply her ghost. In one notable episode, Dexter faked his own death to see how people would react. About 3,000 people attended Dexter's mock wake. Dexter did not see his wife cry, and after he revealed the hoax, he caned her for not grieving his death sufficiently. Dexter also bought an estate in Chester, New Hampshire. He decorated his house in Newburyport with minarets, a golden eagle on the top of the cupola, a mausoleum for himself and a garden of 40 wooden statues of famous men, including George Washington, William Pitt, Napoleon Bonaparte, Thomas Jefferson, and himself. It had the inscription, "I am the first in the East, the first in the West, and the greatest philosopher in the Western World".
Writing
At age 50, Dexter authored A Pickle for the Knowing Ones or Plain Truth in a Homespun Dress, in which he complained about politicians, the clergy, and his wife. The book contained 8,847 words and 33,864 letters, but without punctuation and seemingly random capitalization. Dexter initially handed his book out for free, but it became popular and was reprinted eight times. In the second edition, Dexter added an extra page which consisted of 13 lines of punctuation marks with the instructions that readers could distribute them as they pleased. The first edition was printed on a vanity press in Salem, Massachusetts in 1802. The second edition was printed in Newburyport in 1805.
Legacy
Dexter's Newburyport house became a hotel. Storms ruined most of his statues; the only identified survivor was that of William Pitt. His book remains his primary legacy to this day.
