Robert W. Bailey attended Randolph-Macon College from 1858 to 1861 and enlisted as a private in Company H of the 44th Virginia Infantry when he was 21. On May 1, 1862 he was promoted to 2nd Lieutenant and saw action during the Seven Days campaign. He was wounded at Chancellorsville and again on the second day of the fighting at Gettysburg. He would die as a result of his wounds on the same day. He is buried in Hollywood Cemetery in Richmond.
