Richard Bailey was born into slavery in Albemarle County, Virginia, in 1815, and at some point he was owned by a Mrs. S. Bailey. He enlisted in the Union army at Camp Nelson, Kentucky, a Union army recruiting depot primarily for escaped slaves, on October 31, 1864, for a period of three years. Originally not assigned to a regiment, Bailey likely worked as a laborer in the Department of Kentucky for the first few months of his enlistment. Standing 5 feet, 5 inches tall, he was 49 years old, and was described as having black hair, eyes, and skin. The officer who initially processed the paperwork misspelled his birthplace as "Alabama Co. VA" instead of Bailey's native Albemarle County.

On New Year's Day, 1865, he was mustered in to the 124th USCT Infantry Regiment and assigned to Company B as a sergeant. He was demoted to private on March 22, 1865, due to "incompetency." Bailey's regiment never saw action in the field, and he served as a laborer at various points in the Department of Kentucky. He was detached from the regiment on May 22, 1865, for laborer work in the quartermaster department. According to his service record, he remained in this role until he was mustered out in Louisville, Kentucky, on October 24, 1865. With no pension record available, not much is known of Bailey's life after the war. Census records from 1880 show that Bailey lived with his wife Mandy in Milltown in Chambers County, Alabama. Bailey, then 65, described himself as a farmer.