Descendants of Monticello’s enslaved community on both sides of the color line achieved many “firsts” in government, in the military, and in the workplace. For many, the obstacles that racial prejudice placed in their way only seemed to encourage them in the pursuit of their goals. For some, sacrificing their identity and passing into the white community provided their path to achievement.
Several members of the Woodson family, whose oral history connects them to Monticello, distinguished themselves through military service in the twentieth century. Gen. John Q. T. King served in the Pacific during World War II and retired as a Major General in 1978; he was also a college president. His distant relative Col. James T. Wiley was a Tuskegee airman awarded the Air Medal in World War II. Wiley was always fascinated by aviation, and when racial discrimination prevented him from getting a job in science after college, he began his long military career.
“You were expected to achieve,” Betsy Hemmings descendant Edna Jacques noted in her interview. She grew up in Washington, DC with examples of success all around her. In the capital, “the Negro community was most interesting…[In] every occupation you saw people that you knew so you had no concept of not being able to achieve anything.” Jacques followed in the footsteps of her enterprising forebears and neighbors, and after receiving a Master’s degree in Mathematics from Howard University, she became the first minority hired by IBM in Philadelphia and later the first woman on IBM’s corporate marketing board.
Success and achievement came at a great cost for descendants who passed into the white community. Passing afforded them opportunities denied to African Americans, but it forced them to sever ties with their families and their heritage. After leaving family members in Ohio to start anew as whites in Wisconsin, Eston Hemings Jefferson’s family achieved a position of prominence in the Madison community. Sons Beverly and John Wayles Jefferson became proprietors of hotels in Madison and served in white Wisconsin regiments in the Civil War. John Wayles Jefferson rose from major to colonel, at times in command of the regiment. A highly visible figure in the Union army, he was a man in hiding, only a decade removed from life as a black teenager in Ohio. In the middle of the war, he encountered someone he had known in Chillicothe, who recalled the meeting in 1902:
"I saw and talked with one of the sons [of Eston Hemings], during the Civil War, who was then wearing the silver leaves of a lieutenant colonel, and in command of a fine regiment of white men from a north-western state. He begged me not to tell the fact that he had colored blood in his veins, which he said was not suspected by any of his command; and of course I did not."
Coming of age in Madison’s white community, the Jefferson brothers seem to have identified with their whiteness and used it to their advantage. Without it, John Wayles Jefferson could never have risen high in the military establishment. He left the army in October 1864 and, instead of returning to Wisconsin to live, settled in Memphis, where he became a wealthy cotton broker and acquired plantations across the Mississippi River in Arkansas.