The cataclysm of civil war affected descendants of Monticello's African American community on both sides of the Mason-Dixon Line. For some who were still enslaved, it meant a chance at last to gain their freedom. For others who were living free in the north, it was an opportunity to fight for the cause of freedom. Those fighting for the Union army soon realized, however, that racist sentiments persisted and they would have to struggle to be treated as equals in the ranks. The experience of the soldiers in black Union regiments has often been expressed as fighting a war on two fronts. They not only had to battle the Confederates but also contend with the obstruction and prejudice of white men—in their units and in their government.
Ten descendants of Monticello slaves on both sides of the color line are known to have fought in the Union army. Four, including John Wayles Jefferson and his brother Beverly Jefferson, sons of Eston Hemings Jefferson, fought in white regiments. Other Hemings descendants who maintained their African American identity joined up with “colored” regiments, including the 55th Massachusetts, sister regiment to the more famous 54th Massachusetts depicted in the film Glory.
The Civil War was a seminal event for the descendants of Monticello slaves. For some, it was an opportunity to fight for the cause of freedom. Ten descendants of Monticello slaves on both sides of the color line are known to have fought in the Union army.
For families and individuals who were still enslaved following the dispersement of Jefferson's property, the Civil War and ensuing emancipation provided them with a chance to at last gain their freedom.