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.