Uncovering the Legacy of One of the Earliest Successful Black Settlers in Pittsboro

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The great-great-great grandson of Lewis Freeman looks to his ancestor’s legacy as he studies race, poverty and health outcomes in America

Dr. Harold P. Freeman is a sixth generation descendant of Lewis Freeman
Dr. Harold P. Freeman is a sixth generation descendant of Lewis Freeman, an early Black settler of Pittsboro.

By Jon Spoon and Anna-Rhesa Versola

Born in the same year the Revolutionary War began, Lewis Freeman was at that time considered “a free man of color” who achieved a version of the American dream – owning a home and property. In downtown Pittsboro, the small pewter green house that once belonged to the Black landowner in 1800s Chatham County still stands on Salisbury Street. The building houses Hobbs Architect.

Lewis made sacrifices to accrue the wealth necessary to bring his family out of slavery and secure a future for them. His descendants have gone on to become the first Black dentist in the United States, the first Black American to serve in a presidential cabinet, and a renowned cancer surgeon whose groundbreaking research improved health care today.

“This is an American story, the way I look at it,” says Harold P. Freeman, Lewis’ great-great-great-grandson, during a Zoom interview. “You can tell it in one family through ancestry – a man born in 1775, at the beginning of the country, the beginning of America, who was somehow free by age 25, who became wealthy through property. A man, who had a son by a slave woman, therefore, a son who was a slave, and who ultimately lost his property somehow.”

Though few public records exist from the period before the county’s first major growth in 1830, there is enough evidence to piece together a history of one of the earliest successful Black settlers in Pittsboro. In 1811, Lewis built a one-room house measuring 16 feet by 16 feet, and by the time of his death in 1847, he owned 16 town lots and 20 acres of land, a cow and a horse, according to state archives. “He was a wealthy man for his day,” Harold says. “And his wealth was lost, related to race … so it tells two sides of a story.”

A copy of Lewis Freeman’s will
A copy of Lewis Freeman’s will. Lewis’ son, Waller, was manumitted in 1837 but laws at that time prevented his legal return to North Carolina to inherit property upon his father’s passing.

Harold, who is chairman emeritus and co-founder of the Ralph Lauren Center for Cancer Care and Prevention in New York City, has been researching his family’s history for years. He believes Lewis, who could not read nor write, intended to pass on his property to his wife and son, and entrusted someone to help. “But somehow that failed,” Harold says. “And the person who was arranging the papers for Lewis ended up owning the property. Sadly, it seems like something’s not right.”

In a desire to know more about Lewis, Harold reached out to Henry Louis Gates Jr., the host of a popular PBS documentary television series called “Finding Your Roots with Henry Louis Gates Jr.”

“We were able to discover the ingenious way that [Lewis] invented to free his enslaved son [Waller Freeman],” states Henry in a letter to Harold. “When death set his wife free from this Earth, Lewis took pains to see that their son was set free from slavery in the South, by selling him to a friend who would free him in the North. Since it is highly unlikely that Waller would risk returning to a slave state and being illegally re-enslaved, it is highly likely that Lewis knew, by taking this decision, he would never see his son again. It would take a bloody civil war nearly 30 years later to relieve other Black fathers in the South of that terrible burden.”

Robert Tanner Freeman
Robert Tanner Freeman is another distinguished ancestor for Harold.

Delving into his family’s history inspired Harold. He devoted his career to facing the full impact of racism and poverty on health outcomes. After hearing tales of patients whose cancer had advanced for years while they were ignored and forced to avoid treatment due to a lack of means, Harold came to understand that his patients were having worse outcomes because they were poor and they were poor because of their race. It was the cancer in our society rather than his patients that was proving most difficult to treat.

“I connect all of this to Lewis Freeman,” says Harold, who trained at Memorial Sloan Kettering and spent 40 years as a surgeon in Harlem. He is internationally recognized as an authority on the interrelationships between race, poverty and cancer. In 1990, Harold pioneered the concept of patient navigation to reduce disparities in access to diagnosis and treatment of cancer, particularly among poor and uninsured people. In 2007, the Harold P. Freeman Patient Navigation Institute was established in New York City, located across the street from the New York Stock Exchange.

“I wanted to cut cancer out, but the disease [racism] was so deeply entrenched in the community, I couldn’t cut it out,” Harold says. “I don’t think we can solve these issues unless you understand how they came about, the origins of things going on in politics today where there’s a need for people to understand what happened in the history of America.”

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Anna-Rhesa Versola

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