To his father's great disappointment, Roberts Coles returned to Virginia in 1860, where he became a slaveowner (buying a plantation from a relative) and engaged to Jennie Fairfax of Richmond. After the Civil War began, he enlisted in the Green Mountain Greys and was elected captain. Roberts Coles died (as did the other Confederate captain) during the Battle of Roanoke Island, February 8, 1862.