Career
Bolling was born on January 10, 1819 in Cumberland County, Virginia. After the Civil War Bolling amassed a large amount of property and worked as a farmer, builder, and brickmaker. In 1883 he was elected to the Cumberland County board of supervisors, a position that he was re-elected to the following year.
After losing the election Bolling remained active in politics and participated in Republican Party politics and also worked with the 1888 congressional campaign of John Mercer Langston.
Bolling died on February 8, 1900 in Cumberland County.