Henry Holly was born around 1854 in North Carolina. Holly worked as a laborer and resided in Surry County, North Carolina. Holly was charged with larceny on September 7, 1874, and sentenced to two years in the North Carolina State Penitentiary. Holly was recorded in the North Carolina State Penitentiary's Descriptive Register for the Years 1869-1884 as prisoner number 916. In his sentencing records, Holly's race is noted as "colored." Holly was twenty years old when he was arrested. He was noted as possessing no formal education, meaning he could not read or write at that time. During his incarceration, Holly was leased to the Western North Carolina Railroad Company to work on railroad construction. He was discharged from the railroad on June 30, 1876.