Tom Caldwell was born around 1839 in North Carolina. Caldwell worked as a laborer and resided in Mecklenburg County, North Carolina. Caldwell was charged with larceny on May 18, 1874, and sentenced to two years in the North Carolina State Penitentiary. Caldwell was recorded in the North Carolina State Penitentiary's Descriptive Register for the Years 1869-1884 as prisoner number 885. In his sentencing records, Caldwell’s race is noted as "colored." Caldwell was thirty-five years old when he was arrested. Caldwell was noted as possessing no formal education, meaning he could not read or write at that time. During his incarceration, Caldwell was leased to the Western North Carolina Railroad Company to work on railroad construction. He was discharged on March 29, 1876.