In 1862, Gladeville, present-day Wise, served for a time as the headquarters of Confederate Gen. Humphrey Marshall, who directed operations in Southwest Virginia. Although relatively isolated, the community endured numerous encounters with Union and Confederate forces during the Civil War. A Federal raid on June 1, 1862, led to the capture of preacher and county clerk Morgan T. Lipps, who answered demands to preach to his captors by saying, “I don’t cast pearls before swine.” He later relented and was released, but the Federals burned part of Gladeville before departing. On July 7, 1863, Union Gen. Julius White’s force attacked, completely surprising and capturing the town in street fighting. The prisoners included 18 officers, among them Col. Benjamin E. Caudill, and 99 men of the Tenth Kentucky Mounted Rifles (CSA). In October 1864, Union Gen. Stephen G. Burbridge’s forces passed through Grundy and Crab Orchard on the way to Saltville. Although Burbridge failed to capture and destroy the salt works, a detachment sent to Pound Gap forced its way through and drove Confederate Lt. Col. Clarence J. Prentice from his works at Gladeville, capturing several prisoners, a number of small arms, and one piece of artillery. The Federals left the courthouse in ruins.