Weakley County was sharply divided during the Civil War. Its residents voted to stay with the Union in June 1861 even though most of West Tennessee supported the Confederacy, and at the courthouse local farmer and slave owner John Drewry spoke passionately against secession, declaring on June 8 that those who survived the next six months would eat their next Christmas dinner under the stars and stripes. Although his side won the vote, most county men, more than 1,000, joined the Confederate army. Enlistments began in May 1861 with the formation of the Hickory Blues, Company G of the 9th Tennessee Infantry, at Gardner's Station, and Captains Bradford Edwards, A.C. Gardner, and A.M. Boyd commanded the company during the war. On May 6, 1862, Confederate Col. Thomas Claiborne's 1,300-man 6th Tennessee Cavalry attacked three small companies of the 5th Iowa Cavalry camped 12 miles north of Dresden on the Obion River at Lochridge Mill. While defending a bridge so his men could escape, Union Maj. Carl Schaffer de Boernstein was mortally wounded in a sword fight with Confederate Capt. John G. Ballentine, who was also wounded, and both men were taken in the same wagon to Dresden, where de Boernstein died that night. Eventually almost 400 local men joined the Federal cause. Capt. John Neeley formed Company B of the 7th Tennessee Infantry in November 1862 by enlisting men in Weakley and adjoining Carroll and Gibson Counties. On the day after Christmas, Confederate Gen. Nathan B. Forrest, during his 1st West Tennessee Raid, ransacked the Federal garrison at Dresden and burned a bridge, then bivouacked there overnight to rest, get supplies, and gather intelligence about approaching Union troops. After the war ended, the United Daughters of the Confederacy erected a nearby monument in memory of Weakley County's Confederate soldiers.