Along with the rest of his family, Bolling moved to Cumberland County, Virginia after the American Civil War.
He ran for the House of Delegates in 1883 as a member of the Readjuster Party, but his eligibility was challenged by the Democratic Party, who alleged that he was a resident of Prince Edward County, Virginia and thus not able to represent the counties of Buckingham and Cumberland.
This did not stand well with the Democratic Party, who again challenged Bolling's eligibility despite there being a large amount of evidence that suggested otherwise.
After being removed from office Bolling married Harriet T. Jackson on March 31, 1887, and served on the Prince Edward County board of supervisors.
In March 1892 Bolling was admitted to the Central Lunatic Asylum in Petersburg, where he died on April 18, 1892, from tuberculosis.