Heyward Shepherd was an African-American killed at Harpers Ferry on October 17, 1859, by John Brown's raiders. In life, Shepherd was a porter at the local railroad station and a property owner in nearby Winchester, Virginia. In death, as a free Black man ironically killed by abolitionists during a raid to liberate slaves, he became a symbol to people who believed John Brown's mission had been wrong. Because he was shot while at his job, Shepherd also came to symbolize Blacks loyal to the South.

In 1920, the United Daughters of the Confederacy and the Sons of Confederate Veterans decided to erect a memorial to Shepherd. Opponents were concerned over the intent of the monument, then called the Faithful Slave Memorial, and delayed its placement at Harpers Ferry for a decade. The Heyward Shepherd Memorial finally was sited near the scene of Shepherd's fatal wounding and dedicated on October 10, 1931. The event drew a sharp reaction from W.E.B. DuBois and the National Association for the Advancement of Colored People and proved divisive at Black Storer College, whose administration participated in the dedication.