Samuel Underwood was born around 1818 in North Carolina. Underwood was a saddler who resided in Burnsville (Yancy County), Little River (Catawba County) and Watauga County, North Carolina, with his wife Mary Underwood. Underwood was charged with larceny on May 23, 1878, and sentenced to two years in the North Carolina State Penitentiary. Underwood was recorded in the North Carolina State Penitentiary's Descriptive Register for the Years 1869-1884 as prisoner number 2669. In the federal census, Underwood's race is noted as "mulatto." Underwood was sixty years old when he was arrested. Underwood was noted as possessing no formal education, meaning he could not read or write at that time. During his incarceration, Underwood was leased to the Western North Carolina Railroad Company to work on railroad construction. He was discharged from the railroad on February 18, 1880.