Early Years and Civil War
Bolling was born on February 28, 1835, in Lunenburg County, the son of John Stith Bolling and Mary Thomas Irby Bolling. He grew up on his father’s farm and was educated at Mount Lebanon Academy before moving to Richmond at age nineteen to become a clerk in a store. The following year he and two brothers founded a wholesale grocery and commission business, which they operated until the summer of 1861. On May 9, 1860, Bolling married Cornelia Scott Forrest, of Lunenburg County. They had three daughters and one son.
On June 7, 1861, Bolling enlisted as a sergeant in the Lunenburg Light Dragoons, which became Company G of the 9th Virginia Cavalry Regiment. He was commissioned a lieutenant on April 28, 1862, and promoted to captain on January 17, 1863. Later that year he was detailed to Brigadier General William Henry Fitzhugh Lee‘s staff as acting assistant adjutant general, and in 1864 he was detached to brigade headquarters. At one time Bolling led the largest cavalry company in Major General James Ewell Brown Stuart’s command, and at another he commanded the 9th Cavalry’s fourth squadron of sharpshooters. During the war Bolling sustained six wounds, the most serious being a head injury received at Morton’s Ford on October 11, 1863, after which he required three months of convalescence before returning to duty. He refused towith the remainder of the at Appomattox Court House and led his troops through the lines in a futile attempt to join General in North Carolina. Soon realizing that further warfare was impossible, however, Bolling surrendered and was paroled on April 15, 1865.
Bolling returned to the family farm in Lunenburg County. On July 6, 1869, he was elected to the House of Delegates. He joined a coalition of Conservatives and moderate Republicans in opposition to the Radical Republicans and chaired the Committee on Public Property. Bolling ran for reelection as a Conservative in 1871. He lost by a margin of eighty-two votes to George M. Jennings, an African American and Radical Republican, but the polling was conducted with such flagrant disregard for the law that the House of Delegates refused to seat either candidate and ordered a new election, which Bolling won on February 20, 1872. He served for the remainder of the session in the spring of 1872 and in the regular session in the winter of 1872–1873 but did not receive any standing committee assignments.
In 1870 the governor appointed Bolling a brigadier general of the militia, and in 1875 Bolling became an inspector general of tobacco in Petersburg. He moved to Petersburg and lived there for the remainder of his life. He followed his fellow townsman William Mahone into the Readjuster movement later in the decade and attended the February 1879 convention in Richmond that founded the Readjuster Party. Bolling campaigned for the Readjusters during the 1880s, and in 1882 Governor, another Petersburg Readjuster, named him to the board of directors of the Central Lunatic Asylum. Bolling served as the board’s first president. After the Readjuster Party collapsed, Bolling became a Republican. He ran unsuccessfully for mayor of Petersburg in 1888 and as a Republican candidate for presidential elector that same year. For the next two decades he regularly played a prominent role in the party’s state conventions and on the campaign trail. In recognition of his leadership in the party, Republican presidents twice made Bolling postmaster of Petersburg, from 1882 to 1885 and from 1889 to 1913.
Bolling was a proprietor of the Oaks Tobacco Company in Petersburg. He belonged to the Tobacco Exchange, and he served for eight years as president of the Petersburg Tobacco Association and for several years as vice president of the Petersburg Chamber of Commerce. He also presided over Petersburg’s school board and was active in several fraternal organizations. Bolling’s special interest in Confederate veterans’ groups extended to command in Petersburg of the A. P. Hill Camp of the United Confederate Veterans, service for several years as commander of the 1st Brigade, Virginia Division, of the UCV’s Army of Northern Virginia Department, election as grand commander of the Virginia Division on October 12, 1899, and a stint as major general of the Virginia Division from 1907 to 1913. His sustained popularity among Confederate veterans was all the more remarkable considering his active role in the Republican Party. Bolling died of bronchitis and nephritis at his home in Petersburg on the evening of November 1, 1916, and was buried two days later in Blandford Cemetery.