In 18th-century Middletown, Conn., a tall, dark-skinned man named Prince Mortimer walked the same path each day, trudging to his master’s ropeworks where he spun hemp into yarn.
For over a century, he clung to the hope of freedom—first during the Revolution, then upon his master’s death and finally when his jailers urged him to flee. Yet he died at 110, having spent all but his first six years in captivity.
Today, the route he once walked as an enslaved man bears little resemblance to the path from his enslaver’s mansion to the ropeworks. It evolved into Rapallo Avenue, paved, lined with parking lots, small apartment buidings, a pharmacy and an Italian restaurant. In 2025, Middletown renamed Rapallo Avenue as Prince Mortimer Avenue, ensuring that the man who once walked in servitude is now remembered along the very route he traveled.
Prince Mortimer
Slavers captured him around 1730 at the age of 6 years old near his home in Guinea, West Africa. They shipped him in shackles across the Atlantic Ocean. Prince described the vessel as a “filthy slave ship.”
Prince disappears into the shadows again for the next 15 years. The slave ship may have taken him to a deep-water port engaged in slaving—Newport or Bristol, R.I., or perhaps New London, Conn., or even New York City. Or the ship took him to the Caribbean. There, a smaller vessel that brought horses, lumber or farm produce from Middletown could have carried Prince for sale back in Connecticut.
At 15, an Irish immigrant named Philip Mortimer bought Prince. Mortimer had married a well-to-do Connecticut woman in Boston, and in 1742 they moved to Middletown. Mortimer saw a business opportunity in the busy seaport: It had no ropeworks.
Ships then used tremendous amounts of rope, and Middletown had no ropeworks. So Philip Mortimer started one on the west bank of the Connecticut River.
Rope Spinner
Prince had grown quite tall and clever, and Mortimer had him trained to spin hemp into thousand-foot-long yarn.
When the American Revolution broke out, Connecticut passed two laws that gave enslaved men hope for freedom. Under the first, men could avoid the draft by finding a substitute. Under the second, men could avoid conscription by freeing an enslaved person to serve in their place, which also released them from any future responsibility for that person’s welfare.
The colony didn’t guarantee freedom for enslaved soldiers, but many negotiated freedom as the price for their service. But some didn’t get such a promise, and others didn’t get it in writing.
Prince Mortimer may have negotiated for his freedom if he fought for freedom from Great Britain. He probably at least had hope of liberty.
Pvt. Mortimer was said to have been a servant to the Army’s top officers, carrying messages back and forth. He supposedly ran errands for George Washington. Mortimer himself said he “straddled many a cannon while fired by the Americans at the British troops.”
When the war ended, Prince Mortimer returned to servitude. If Philip Mortimer promised him freedom for serving, he was far from the only slave owner who broke that promise.
Another Shot at Freedom
Philip Mortimer did promise in his will to set him free upon his death. But when he died in 1794, his son-in-law, George Starr, successfully challenged the will. And so at the age of 70, Prince Mortimer found himself enslaved to Starr, a successful local merchant who had served as Connecticut’s quartermaster during the Revolution.
According to Middletown’s Christ Church records, Prince married a woman named Ann. They had three children, Samuel, Zilpah and John. Ann and the three children were baptized in 1803 at the church.
Prince Mortimer remained enslaved for 17 years. At 87, his usefulness to George Starr neared an end. And Starr had an old man on his hands who he had to feed, clothe and shelter.
So George Starr accused Prince Mortimer of trying to kill him by putting arsenic in his breakfast chocolate. He said he noticed particles in the drink, later identified as ratsbane or arsenic. A court found Prince Mortimer guilty and sent him to Newgate Prison — a place also known as hell.
Old Newgate Prison
It had started out as a colonial copper mine in Simsbury, Conn. (later East Granby). But it didn’t make the kind of money its owners dreamed of.
By 1773, Connecticut Colony decided to turn it into a prison. The colony’s officials thought that confining prisoners in a cold, dark, wet, filthy hole in the ground was less barbaric than the common punishments of branding, ear cropping and whipping.
They named it “Newgate” after England’s notorious penitentiary.
Drains were closed, the main shaft, about 40 feet deep, was capped and a guardhouse was built over it. The mine had a second shaft, 80 feet deep, through which prisoners could escape if an accomplice threw them a long enough rope.
Prisoners had to climb down a ladder into the mine, a dark, cold cavern. Bugs and five inches of slippery filthy covered the floor. During the day, prisoners worked above ground, making barrels, plows, shoes or baskets.
Prince Mortimer, Inmate
To his captors, Prince appeared a harmless, clever old man, according to one historian.
Prison guards let Prince leave Newgate, perhaps because of his age and temperament, or perhaps they considered him a burden and wanted him to escape. Prisoners gave him money to go across the road to buy spirits at the nearby tavern.
Prince once did what the prison guards wanted and escaped. He traveled back to Middletown, 35 miles away, and rambled about, looking for someone he once knew. But he couldn’t find anyone, so he returned to the prison and begged the guards to take him back.

Old Newgate today. Run by the State of Connecticut as Old New-Gate Prison & Copper Mine Archaeological Preserve., it is o National Historic Landmark and open to visitors seasonally.
Connecticut closed Newgate in 1827 and moved the inmates, including 97-year-old Prince Mortimer, to the new prison in Wethersfield.
Prison records show that in 1831 Prince suffered from ailments of the bowels caused by the prison food. Admitted to the prison hospital, physicians prescribed better food.
On March 11, 1834, Prince Mortimer died. The prison physician wrote that he died of old age, “no bodily disease at the time of his death sufficient to produce such a result.”
Recognition
in February 2025, Middletown renamed Rapallo Avenue, the old path to the ropewalk, Prince Mortimer Avenue.
John Mills is a software engineer and historian who has dedicated himself to uncovering and preserving stories of enslaved people in Connecticut, including Prince Mortimer. Through the Alex Breanne Corporation, he has traced the roots of 50 families to date, sharing their histories to ensure that the past is not forgotten.
Most of the enslaved people in his family spent most of their lives enduring, Mills told WBUR in 2025. “But because they persisted, I exist. I see greatness in their endurance.”
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Images: Drawing of Newgaate, A view of the guard-house and Simsbury-mines, now called Newgate – a prison for the confinement of loyalists in Connecticut. London: J. Bew, Pater-Noster-Row, Nov. 1st. Photograph. Retrieved from the Library of Congress, <www.loc.gov/item/2004671519/>. Picture of Newgate ruins, Highsmith, Carol M, photographer. Old New-Gate Prison in East Granby, Connecticut. October. Photograph. Retrieved from the Library of Congress, <www.loc.gov/item/2012630946/>. Illustration of Prince Mortimer by ChatGPT>



































