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London Pleasants was a Black teen who risked his life to escape slavery by serving in the British Army during the Revolutionary War, rather than live in bondage in Virginia.
John Pleasants, the man who enslaved London, desired to eventually free his slaves, as slavery was against his Quaker faith. More than a decade after the end of the war, his son successfully challenged his relatives in the Virginia Supreme Court to free those enslaved by Pleasants, honoring his late father’s will.
The 1799 Pleasants v. Pleasants ruling was the largest court ordered manumission of enslaved people in U.S. history. But freedom wasn’t immediate for many of the more than 400 people at the center of the case. Liberty was granted once they reached 30 years of age.
London Pleasants didn’t want to wait on a promise that may have never come. He seized his freedom by joining Loyalist forces led by General Benedict Arnold — the famed turncoat.
Historians wonder what Pleasants thought about the risk of fleeing to enlist in Arnold’s American Legion, said Adrienne Whaley, a historian at the Museum of the American Revolution in Philadelphia.
“Benedict Arnold had just tried to turn West Point over to the British in 1780, so he’s a known turncoat,” Whaley said. “Yet this young man is willing to trust him with his life.”
In 1781, Arnold’s men marauded and set fire to plantations between Williamsburg and Richmond, and destroyed much of the capital city, after then-Gov. Thomas Jefferson refused to surrender. To deal a blow to Patriots along the way, Arnold promised to free slaves who escaped to enlist.
Pleasants, who was around 15, and his uncle, Carter Jack, were among more than 20 men enslaved on the Curles Neck plantation in Charles City County who joined Arnold after the burning of Richmond.
Not much is known about Pleasants, as there are few primary sources surrounding his life. But it’s clear he was brave and self-determined, Whaley said.
“Maybe [he had] a desire to grasp onto anything for freedom, at any cost,” she said.
The boldness of youth may have also been a factor in Pleasants’ decision, Whaley wagers. “Teenagers are … more willing to be daring, stretch out on their own and develop their identities,” she said.
What is certain is that Pleasants faced a life-changing decision shared by many Black people during the Revolutionary War. At various points of the conflict, both Patriot and Loyalist generals enlisted enslaved people in exchange for freedom after service.
An estimated 20,000 or more runaway slaves joined Loyalists, and only 5,000 Black men, free and enslaved, served in the Continental Army, mostly within integrated units. Often, Black Patriot soldiers were forced to serve as substitutes for their masters or were slaves owned or hired by the government.
More Black people may have sided with Loyalists because they had been held in bondage by Patriots, said Tommy Bogger, retired professor of history at Norfolk State University.
“For the great majority of Blacks, if they didn’t know anything about the British, it’s just common sense that if you’re the enemy of my master, you are a potential friend of mine,” Bogger said.
A significant court case also led enslaved people to view the British as more likely liberators, and many thought slavery had ended in Great Britain. In 1772, James Somerset, an enslaved man living in London, had won a suit against his owner for his freedom.
But the motivations of Arnold and other British generals for enlisting slaves were strategic, not moral, said Mark Shubert, a Henrico historian.
“He should not be viewed as a liberator with good intentions,” Shubert said. “He obviously wanted to stir the pot and make his adversaries scared and it worked.”
Pleasants served as a trumpeter in battles in Virginia, before sailing with the American Legion north to continue Arnold’s campaign in New York and Connecticut. As trumpeter, Pleasants relayed Captain commands to soldiers that could be heard above the melee.
Pleasants saw the most action in Connecticut. In September of 1781, Arnold laid siege to New London, leaving the port city in ruins. Days later, in the bloody Battle of Groton Heights, his forces slaughtered Patriot troops that served at forts in the area, after they had already surrendered.
“Even though they offered their swords, they were shot, stabbed, killed,” Whaley said. “London would have been playing his trumpet and helping to communicate the orders the British were following during that.”
(See our previous story about how music served as a signalling system on the battlefield.)
A month later, the Patriots won their independence when the British surrendered at Yorktown. The danger for Black veterans on either side of the conflict wasn’t over.
After the war, the British largely kept to their word and evacuated Black soldiers to territories held by the crown in Canada. But they didn’t stop slave catchers from capturing Black veterans. Black Patriots were often freed, though many were re-enslaved after service.
Pleasants was among the roughly 3,000 Black men, women and children who sailed to modern-day New Brunswick (then still part of Nova Scotia) in Canada to begin a new life. Not leaving would have put Pleasants in danger of re-enslavement in America. (See our previous story about how 900 formerly enslaved Virginians fled to Canada after the war as well as our podcast on the subject.)
In September 1783, he fled on a ship known as the Elizabeth, alongside ten other Black people, four of whom were still enslaved, and more than a hundred white Loyalists.
Many white Loyalists left the former Colonies with thousands of the people they enslaved, settling in Canada, Florida and British territories in the Caribbean.
Pleasants and other newly freed Black people faced discrimination from white Loyalists in Canada. In 1792, about 1,200 returned to Africa and settled in Sierra Leone, while 400 sailed to London.
Pleasants’ life as a free man living in peace time was brief. He died sometime between 1783 and 1785, a record of his unit shows. His death came before he would have received a plot of land in New Brunswick, and could have been caused by disease or the harsh winters and living conditions of the time.
“[Pleasants’ life] is the gripping story of a 15-year-old boy going out on his own, finding his freedom … tragically cut short,” Shubert said. “But, nonetheless, a brave and awesome story.”
