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This conversation has me thinking about Prince Demah, the enslaved portrait painter from Boston whose enslaver, Henry Barnes, brought him to London in 1771 (before the Somerset decision). Barnes definitely worried about Black antislavery activism in London in 1771.
Prince Demah (1741-1778) was a talented artist (one of his portraits is currently on display at the Met). His mother, Daphney, was enslaved by Henry and Christian Barnes, a rich white couple from Marlborough, Massachusetts.
In 1769, Prince made a sketch of Christian Barnes and Henry liked it so much that he bought Prince with the “design of improving his genius in painting.”

Sources: Murray-Robbins Papers @MHS1791, “Prince Demah Barnes” by Amelia Peck and Paula Bagger themagazineantiques.com/article/prince…
Christian Barnes got excited about the prospect of exhibiting Prince and his works. She wrote to friends about his portraits (and self-portrait!), saying she thought he captured her likeness better than Copley had. (3/20/1770) @MHS1791
In 1771, Henry brought Prince to London to get more training as an artist. Prince became a student of the engraver John Pine, who Barnes believed had “taken him purely for his genius.”

en.wikipedia.org/wiki/John_Pine
Henry worried that Prince would talk to free Black people in England and try to gain his freedom. In a letter to his friend Elizabeth Murray (2/12/1771), he wrote, “Prince comes on extremely well, he is with a Mr. Pine who has taken him purely for his genius Mrs. Wright . . .
tells me I shall carry him a Treasure to America. but I have met with so many disappointments in life that tho late I have learnt not to be too sanguine in my Expectations indeed his life and situation are so precarious if he should even attempt his Freedom it would give me . . .
such a disgust to him I should not overlook it I want you should return with Bill for I do not let him converse with any of his own colour here.”
Note: Some biographies of John Pine note that he may have had African ancestry. Henry Barnes seems not to have considered Pine to be Black, given that he explicitly forbade Prince speaking to Black people, but that doesn’t mean that he wasn’t.
royalacademy.org.uk/art-artists/wo…
In any case, Henry Barnes definitely thought that Prince might “attempt his freedom” in England, especially if he could get support from free Black Londoners. He imagined England as a place where his control over the man he enslaved was “precarious.”
Prince Demah returned to Boston with Henry. In 1773, Boston papers ran ads for the services of “a Negro Man” who “takes Faces at the lowest rates.” This may have been when Demah painted the portrait of William Duguid that hangs at the Met.
Only three of Demah’s portraits are currently known, but he painted others. Last year, I wrote about a receipt for one of his portraits recently discovered during Harvard’s Colonial North America digitization project.

In one of her letters, Christian Barnes speculated that Prince Demah had “tory principles.” This turned out to be false. During the American Revolution, the (Loyalist) Barneses fled and Prince self-emancipated to serve in a patriot artillery regiment.
Prince Demah died in 1778. His will identifies his occupation as “Limner” i.e. portraitist.

Portrait of William Duguid by Prince Demah, 1773, Metropolitan Museum of Art
metmuseum.org/art/collection…
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