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He once followed this path to his enslaver's mansion. Now, the same CT street bears his name

On the first day of Black History Month, a Connecticut town that was once a hub of the transatlantic slave trade renamed a street in honor of a man, who once lived and toiled in town. Rapallo Avenue is now “Prince Mortimer Avenue,” In Middletown, Connecticut.
John Mills
On the first day of Black History Month, a Connecticut town that was once a hub of the transatlantic slave trade renamed a street in honor of a man, who once lived and toiled in town. Rapallo Avenue is now “Prince Mortimer Avenue,” In Middletown, Connecticut.

On the first day of Black History Month, a Connecticut town that was once a hub of the transatlantic slave trade renamed a street in honor of a man, who once lived and toiled in town. Rapallo Avenue is now “Prince Mortimer Avenue.”

Prince Mortimer “was an enslaved man in Middletown, Connecticut, from the early 1700s,” said historian John Mills. “He was purchased by an enslaver named Philip Mortimer in Middletown sometime after 1754 and spent most of his life there enslaved — making rope.”

Mills is a software engineer and historian who has dedicated himself to uncovering and preserving stories of enslaved people in Connecticut through his nonprofit Alex Breanne Corporation. He said during the Revolutionary War, Prince Mortimer served as an assistant to officers, even running errands for George Washington. However, unlike some enslaved people who secured their freedom after the war, Mortimer’s story took a different turn.

“Late in life, he was supposed to be freed,” Mills said. “But that got overturned, and he continued to be enslaved, later being sent to prison, accused of attempting to poison his new enslaver, and he spent from the age of 87 until the age of 110 in prison.”

A different kind of legacy

A reimagined painting of Prince Mortimer, by New Jersey artist Kern Bruce is part of a display to celebrate Black History Month at City Hall in Middletown, Connecticut..
John Mills
A reimagined painting of Prince Mortimer, by New Jersey artist Kern Bruce is part of a display to celebrate Black History Month at City Hall in Middletown, Connecticut..

While history often highlights figures like Frederick Douglass, who escaped bondage and became a celebrated author and statesman, Mills says Mortimer’s experience reflects a different but equally significant reality.

“I discovered that most of the enslaved people in my family don’t have that Frederick Douglass story,” Mills said. “Most of them spent most of their lives enduring, and they died. But because they persisted, I exist. I see greatness in their endurance.”

Mortimer’s story, he believes, is one that resonates with many African-Americans whose ancestors may not have been famous, but whose perseverance ensured the survival of future generations.

“He survived for 110 years, and he persisted and endured with grace,” Mills said. “I think that aligns more appropriately to many African Americans’ lineage, and so we celebrate that. We celebrate his perseverance, his endurance, and his grace in doing all of that.”

A 'street' Mortimer knew well

This 1870s photo shows the walkway leading away from the enslaver's mansion. “It was a walkway that was built by his enslaver, Philip Mortimer," Mills explained. "And it only led to the enslaver’s mansion. And Prince would walk up that walkway every day to get to Main Street to get to the enslaver’s rope-making facility.”
Provided by John Mills
This 1870s photo shows the walkway leading away from the enslaver's mansion. “It was a walkway that was built by his enslaver, Philip Mortimer," Mills explained. "And it only led to the enslaver’s mansion. And Prince would walk up that walkway every day to get to Main Street to get to the enslaver’s rope-making facility.”

The choice of Rapallo Avenue for Mortimer’s honorary renaming was deliberate – even though the thoroughfare was not named as such in Mortimer’s day.

“That street used to be a walkway,” Mills explained. “It was a walkway that was built by his enslaver, Philip Mortimer, and it only led to the enslaver’s mansion. And Prince would walk up that walkway every day to get to Main Street to get to the enslaver’s rope-making facility.”

Mills believes having Mortimer’s name placed atop what was once a path of servitude represents a symbolic act of reclamation and acknowledgment.

Changing the narrative

Prince Mortimer “was an enslaved man in Middletown, Connecticut, from the early 1700s,” said historian John Mills. “He was purchased by an enslaver named Philip Mortimer in Middletown sometime after 1754 and spent most of his life there enslaved — making rope.”
Erica Mills
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Provided by John Mills
Prince Mortimer “was an enslaved man in Middletown, Connecticut, from the early 1700s,” said historian John Mills. “He was purchased by an enslaver named Philip Mortimer in Middletown sometime after 1754 and spent most of his life there enslaved — making rope.”

In recent years, discussions about how the U.S. remembers its history have become contentious. Laws restricting how racial history is taught in schools have been passed in several states, often citing concerns about making white students uncomfortable. Mills rejects that rationale.

“That idea of making sure that we don’t impose this on young white children? That was imposed on me as a young Black kid,” he said. “That lack of an ability to feel a reverence for people that I am related to, and this is the intent to kind of change the narrative of how we see the enslaved, and give to young Black kids a reason to revere their genealogy, even if they’re not related to a Frederick Douglass or a Martin Luther King.”

Mills sees the honorary renaming of Prince Mortimer Avenue as a step towards that goal — one that recognizes not just one man’s endurance, but the endurance of so many whose names may never be widely known.

For Mills, this is just one of many efforts to reclaim and preserve Black history. 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.

John Henry Smith is Connecticut Public’s host of All Things Considered, its flagship afternoon news program. He's proud to be a part of the team that won a regional Emmy Award for The Vote: A Connecticut Conversation. In his 21st year as a professional broadcaster, he’s covered both news and sports.

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