However, he soon left to join the Confederate Army in the Fifteenth North Carolina Infantry Regiment, in which he served until badly wounded at the Battle of Malvern Hill on July 1, 1862.

In the spring of 1864, he re-enlisted as a private in the Second North Carolina Cavalry Regiment and had risen to the rank of Captain by the time of his capture on April 3, 1865, after the Battle of Namozine Church.

[3] After the conclusion of the Civil War he returned to UNC, graduating in 1868 and subsequently teaching at Horner Military School in Oxford, North Carolina until 1870.

In 1886, after Culleoka incorporated and legalized the sale of liquor in the new city, he (being a prohibitionist) moved the Webb School to Bell Buckle, where it still exists today.

Always a prohibitionist, he delivered his one speech in the Senate to support a law prohibiting interstate transport of liquor.