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Virginia Isaacs, daughter of Tucker and Ann-Elizabeth Fossett Isaacs, was raised on a farm in Ross County, Ohio.  After the Civil War she and her sister Maria Elizabeth Isaacs married two veterans of the Civil War, Lts. James Monroe Trotter and William H. Dupree.  Both couples settled in Boston, where Trotter and Dupree were well-known figures after distinguished service as officers in the 55th Massachusetts Infantry regiment.  Virginia Trotter and her sister were described by a contemporary as women of “charming sociability and cultured manners.” 

The Trotters lived in Hyde Park, a largely white suburb of Boston, and accumulated property, particularly after James Monroe Trotter’s appointment to the lucrative position of Recorder of Deeds for the District of Columbia.  They had three children, William Monroe, Maude, and Bessie.  After her husband’s early death, Virginia Trotter managed the family investments and supported her son Monroe, allowing him to establish the Boston Guardian, and become a leading voice in the early civil rights movement.

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.”

Virginia Rose was the daughter of Elizabeth Letitia (Bessie) Trotter and Henry Kempton Craft, a Harvard graduate, electrical engineer, teacher, and YMCA executive.  He was the grandson of William and Ellen Craft, famous for their daring escape from slavery in 1848.  Bessie Trotter, who attended the New England Conservatory of Music, was the sister of the prominent civil rights leader William Monroe Trotter.

Virginia Rose attended the University of Pittsburgh, graduated from Barnard College, and did graduate work at Western Reserve University.  She married Joshua Rose in 1934 and they moved to California, where he headed the Oakland branch of the YMCA.  She passed her pride in her Trotter and Craft heritage along to their three children, who shared memories of cross-country car trips to keep up with their East Coast roots.  Only late in life did Mrs. Rose begin to “ponder” her connection to the Fossetts of Monticello.  As she said in 2006, “You don’t know who you are until you know where you came from.”

Peggy Preacely, a writer, filmmaker, and public health worker, learned her family history from her mother, Ellen Craft Dammond, the “griot of the family,” who recognized that “there were wonderful stories that needed to be kept alive in the family.” Her mother was a niece of William Monroe Trotter as well as a descendant of the famous fugitive slaves William and Ellen Craft. 

Mother and daughter both participated in the civil rights movement. Ellen Dammond worked with Dorothy Height and Polly Cowan in the Wednesdays in Mississippi initiative. Peggy Preacely, who sees herself as carrying on a double family line of “freedom fighters,” joined the Student Nonviolent Coordinating Committee and was jailed for sit-ins in the south. As she said, “I had to do something in my lifetime to make a difference because Uncle Monroe did and the Crafts escaped from slavery.”