His father was James T. Bolling. A Clerk that joined the Ninth Regiment of Virginia Cavalry in defense of his homeland, he rose to Captaincy, and eventually commanded the largest Company under Jeb Stuart. In 1896 Bolling was elected to the Virginia House of Delegates. In 1870 the Governor appointed him a Brigadier General in the State Militia. In 1875 he became Inspector General of Tobacco in Petersburg. He moved there and remained the rest of his life. His exemplary activity in the United Confederate Veterans caused him promotion to Major General within that group. He was proprietor of Oaks Tobacco in Petersburg, a member of the Tobacco exchange, and was President of the Petersburg Tobacco Exchange. He was Vice President of the Chamber of Commerce, presided over the Petersburg School Board, and was Postmaster.

His father was James T. Bolling. A Clerk that joined the Ninth Regiment of Virginia Cavalry in defense of his homeland, he rose to Captaincy, and eventually commanded the largest Company under Jeb Stuart. In 1896 Bolling was elected to the Virginia House of Delegates. In 1870 the Governor appointed him a Brigadier General in the State Militia. In 1875 he became Inspector General of Tobacco in Petersburg. He moved there and remained the rest of his life. His exemplary activity in the United Confederate Veterans caused him promotion to Major General within that group. He was proprietor of Oaks Tobacco in Petersburg, a member of the Tobacco exchange, and was President of the Petersburg Tobacco Exchange. He was Vice President of the Chamber of Commerce, presided over the Petersburg School Board, and was Postmaster.