From at least the 1790s, there were enslaved people at Monticello who were white enough to pass for white. Elizabeth (Betty) Hemings's grandchildren chose different paths for making their way in the world. Some crossed the color line to escape the racial prejudice that blighted their dreams for their families. Others, like Madison Hemings, continued to identify themselves as people of color. Over the generations, some of his descendants also resorted to either permanent or intermittent passage across the color line. They might be white in the workplace and black at home. Or they might spend half a lifetime on the far side of the line, returning to family and the black community when in need of support.
Three of Sally Hemings's children passed permanently into the white world. Her son Beverly and daughter Harriet left Monticello with Jefferson's consent in their early twenties. Both married and had children, whose descendants are unknown today. Her son Eston Hemings, freed in Jefferson's will, married and took his family to Ohio in the late 1830s. At midcentury, they moved to Wisconsin, where they changed both their name—to Jefferson—and their racial identity. While Eston H. Jefferson's descendants prospered, they learned that passing has costs as well as benefits, because of separation from family and community and the persistent anxiety of hiding the past.
"He had crossed over"
Diana Redman remembers the sudden appearance in her grandmother's household of an unfamiliar relative.