Hillery C. Cunningham was born into slavery on November 10, 1861, to Good and Susan Cunningham, and was the second of five children. As a young man he began as a poor, humble cotton farmer, but over time he accumulated land and wealth and, professionally known as "Hill," established himself as one of the most successful businessmen in Upson County. He held community positions that were unheard of for African Americans at that time, including Treasurer of the Thomaston Chapter of the Red Cross in 1918. Cunningham also gave back to his community as a philanthropist and was described as very liberal in the matter of churches and schools. Shortly before his death in 1936, he offered to donate $5,000 for a consolidated church school in the Logtown Community if the Board of Education would contribute a like sum. He died on July 19, 1936, and hundreds of white and black mourners came to pay their respects to one of Thomaston's most beloved citizens.