William Monroe Trotter, the most famous of known descendants of Monticello's enslaved families, was the son of Virginia Isaacs and James Monroe Trotter. He graduated magna cum laude from Harvard, which he viewed as the exemplar of “real democracy.” But his world began to contract, as the Jim Crow line moved inexorably up from the south. He gave up a lucrative real estate business to start a newspaper, the Boston Guardian, and raised his voice against the accommodationist principles of Booker T. Washington. In 1905 he and W. E. B. Du Bois took the lead in founding the Niagara Movement, the precursor of the NAACP.
In his long, militant and uncompromising fight for "full equality in all things governmental, political, civil and judicial," Trotter presented petitions, led picketing and demonstrations, and confronted presidents in the White House. His last national effort was described at the time as a movement for "the fulfillment of the preamble of the Declaration of Independence."