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John Quincy Adams’ Bad Boy Brother Charles

He started out as charming, sensitive and delicate

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John Quincy Adams’ diary must have been irresistible reading for his bad boy brother Charles.

John Quincy started his diary at the age of 12 because his father insisted on it. He made his first entry on the eve of his voyage to Paris with his father and Charles, then nine.

Bad boy brother Charles and John Quincy Adams in their youth.

On Nov. 19, 1779, John Quincy wrote, “This morning at about 11 o’clock I took leave of my Mamma, my sister, and brother Tommy and went to Boston with Mr. Thaxter, in order to go on board the frigate the Sensible of 28 pounders.”

John Quincy had already accompanied his father once on a diplomatic mission to France during the American Revolution. He had been sturdier and older than Charles, described as “charming,” “sensitive” and “delicate.”

Story of a Bad Boy

The second diplomatic mission starting in 1779 turned out a disaster for young Charles. The Sensible headed into a gale and then sprung a leak. The captain enlisted passengers, including John Quincy, to take turns pumping the ice water out of the ship. The Sensible limped into El Ferrol, the first friendly port it could find, on the northwestern tip of Spain. The Adamses then traveled 1,000 miles overland in a journey John Adams called the worst experience of his life. After a brief time in Paris, they went on to the Netherlands, where John Adams negotiated a loan from the Dutch to the continental American government.

John Adams

John Adams upon completion of the Treaty of Paris. Courtesy Harvard Art Museums.

John Quincy and Charles enrolled in a Latin school in Amsterdam where the tutors beat them regularly. Their father found out and sent them in December 1780 to another school, the prestigious Leiden University. John Quincy, though, left for St. Petersburg in July as secretary to Francis Dana. The boys’ father realized Charles was terribly homesick and sent him back to Massachusetts.

Charles left London with a chaperone in August of 1781, but his ship didn’t get far. Needing repairs, it went into drydock in Spain. The Adams family didn’t know what happened to him and thought he’d been lost at sea. He arrived home five months later, but by some accounts he had returned a lost boy.

Little survives of the notoriously voluminous Adams’ family papers when it comes to Charles’ disappearance in Spain. Or much else about Charles.

John Quincy kept up his diary for a few months after he embarked on the Sensible, but stopped writing during and after Charles’ departure.

A Sad End

Five years later, in July 1786, Charles had finished his first year at Harvard. He had already started getting into trouble at Harvard, drinking heavily and disturbing the peace.


John Quincy Adams

John Quincy had just been admitted as a junior to ‘the Seat of the Muses,’ as his father called his alma mater.  He had started keeping his diary again, and on July 27, 1786, he wrote about something else his bad boy brother had done.

“I perceive Charles has been guilty of a trick which I thought he would despise; that of prying into, and meddling with things which are nothing to him: and ungenerously looking into Papers, (which he knew I wished to keep private,) because I could not keep them under lock and key. If he looks here, he will feel how contemptible a spy is to himself, and to others.”

Charles did graduate from Harvard, and his parents sent him to New York to study law. He lived with Baron von Steuben, believed to be gay, and found him fascinating. Eventually he married, but he had extramarital affairs and failed at the law. Some historians believe Charles was gay as well.

His father later disowned him as a “a mere rake, buck, blood and beast.” Charles died at 30 of cirrhosis of the liver while living in poverty apart from his wife and two daughters.

John Quincy had another bad boy brother: Thomas. The baby of the family, Thomas ended up living with his parents, along with his wife and seven children. He couldn’t support himself or his family, and he vanished for days on drinking binges. He died at 59.

Like Father, Like Son

John Adams famously wrote to his eldest son that he’d only have himself to blame if he didn’t rise to president of the United States.  “You come into life with advantages which will disgrace you if your success is mediocre,” he wrote. “And if you do not rise to the head not only of your profession, but of your country, it will be owing to your own laziness, slovenliness, and obstinacy.”

Some speculate that John Adams’ two youngest sons failed under the pressure of his demands.

John Quincy Adams

John Quincy Adams also demanded a great deal of his sons. And like his father, he would have one son who would make him proud and two who would disappoint him.

George Washington Adams

George Washington died at 28, a dissolute drunk who fathered an illegitimate child and may have committed suicide. John lived until 31, but led no happier or soberer a life than his older brother. Only the youngest, Charles Francis Adams, would win acclaim as a diplomat and historian.

John Adams II

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Read more about the Adams’ families in Eat Like a President, from the New England Historical Society. Click here to order your copy. 
This story last updated in 2024.

With thanks to J.L. Bell and his Boston 1775 blog and Steven Lee Carson, Adams Family (History Net).

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