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“I knew, wow, I have slaves in my family, and I would like to know who they are,” he said. “It was an amazing pastime for me. It kept my mind off the fact that I knew that Monday morning I would have to go back to school and get bullied again.”

Dennis’s great-uncle, John Sherman Merritt, said it had been very difficult to get information from his elders, especially the great-grandmother who had been born before Emancipation and grew up during Reconstruction.

Through his searches he came across the work of a fifth cousin, Teresa Vega, a generation older, who was already engaged in a rigorous study of their ancestors from her apartment in Upper Manhattan.

His father, Dennis Sr., knew that there were family mysteries to be unraveled, though he had not tried to unlock them himself. Many of his relatives“don’t look like they’re of African descent,” he said. “Just visualizing our family, you can see that there’s a relation to different ethnic groups.”

Hangroot was a community once vibrant, but largely lost to history; its Black and Indigenous residents were mostly gone by 1910 — “gentrified out,” said Ms. Vega, by the twofold pressure of white immigrants and the arrival nearby of the Rockefellers. When a relative gave Dennis a photograph from around 1899 showing his great-great-grandfather as a boy in Hangroot, it put a face on an ancestor and a community Dennis knew only from documents.

Dennis learned about the great-great-grandfather in the photograph, how he worked himself to death at 31, and about his mother, born in 1871 in Virginia, the daughter of enslaved parents, who wrote poems that were published in newspapers.

Against his difficulties in school, his ancestors became role models. “Because grandpa John died of exhaustion, if I’m not dying from working hard, then why wouldn’t I continue to work hard?” Dennis said. “If I know that one of my ancestors couldn’t read and write for a few years because of the circumstances they were born into, but taught themselves how to do it, why wouldn’t I go online and look up a word that I didn’t know? So I’m learning from these stories. I’m not just finding these things out. They’re empowering me.”

Further searches revealed relatives of Mohawk descent.

Finally, an archivist at the Rye Historical Society found a bill of sale that Dennis realized referred to his sixth great-grandmother, Margaret Lyon, known as Peg, dated July 7, 1790. For the sum of “Fifty Pounds of New York Money,” she became the legal property of Nathan Merritt Jr., after whose family the Merritt Parkway in Connecticut is named.

Through DNA testing on numerous branches of the family, Mr. Richmond and his cousin Ms. Vega said they were able to determine that Peg bore at least one child — Mr. Richmond’s fifth great-grandfather, who was born into slavery — with a member of the white Merritt family that enslaved her.

Ms. Vega took the genealogy back a generation further. Peg Lyon, she found, was herself fathered by a man from the family that sold her to the Merritts, the Lyons, a comparably prominent family whose name is given to a park in nearby Port Chester, N.Y. Again, DNA testing confirmed her research.

She followed a family trail to Christine Varner, a Lyon descendant still living in Connecticut. Ms. Varner, who is white, said she always believed she might have relatives of African descent. Then Ms. Vega called.

In her childhood, her mother had taken her to the old African-American and Native American cemetery to place flowers on the graves. Now she understood why.

In the meantime, he said, his genealogy had given him a view of Black history far different from the one he’d learned in school — one that included Northern families like the Lyons and Merritts, Black and white, living in the same community for generations. During the pandemic, he wrote and self-published a book that included his adventures in genealogy, “He Spoke at My School.”

“To know that I have Indigenous DNA, on my dad’s side, just makes for a true American story,” he said. “You had slave owners who had slaves, and who had children with the people that they enslaved. You have people who came to this country from Europe and who had children with Indigenous people. And Indigenous people who had children with stolen Africans.

“And then you speed up hundreds of years,” he said, “and you have Dennis.”