Charles Askew was born around 1858 in North Carolina. Askew worked as a laborer and fireman who resided in Halifax County, North Carolina, and later Winton (Hertford County), North Carolina, with his wife Millie Askew and their children. Askew was charged with larceny and receiving stolen goods on May 6, 1878, and sentenced to two years in the North Carolina State Penitentiary. Askew was recorded in the North Carolina State Penitentiary's Descriptive Register for the Years 1869-1884 as prisoner number 2693. In the descriptive register, Askew's race is noted as Black. Askew was twenty years old when he was arrested. Askew was noted as possessing no formal education, meaning he could not read or write at that time. During his incarceration, Askew was leased to the Western North Carolina Railroad Company to work on railroad construction. He was discharged from the railroad on March 2, 1880.