John Robinson Waddy was born on December 29, 1834, in Eastville, Virginia, to Edward Robinson Waddy and Harriet Nottingham. He grew up in Northampton County, Virginia, and his father owned at least 10 enslaved laborers. He enrolled at the Virginia Military Institute in 1849 and graduated in 1853 before becoming a teacher. He joined the United States army in February 1857, mustering in as a 2nd lieutenant in the 4th United States Artillery. He was promoted to 1st lieutenant on February 4, 1861, but he resigned in July 1861 and joined the Confederate army.
Waddy mustered in as a 2nd lieutenant in the Confederate artillery. He earned a promotion to major soon afterward and served as an assistant adjutant general. He became a lieutenant colonel in General Joseph E. Johnston’s army on November 22, 1862, and he eventually became an artillery colonel. He surrendered as part of Johnston’s army in April 1865 and received his parole on May 1, 1865.
He returned to Northampton County after the war, and he married Ella Fitchett there around 1868. They had at least four children: Harriet, born around 1869; Mary Anna, born around 1875; Rebecca, born around 1876; and Edward, born around 1879. They moved to Jersey City, New Jersey, around 1868, and he worked as a merchant there.
They moved to New York City soon afterward and remained there until around 1877. By 1880, they were living in Eastville, Virginia, and Waddy was working as a farmer. He employed at least three Black laborers. The family moved to Norfolk, Virginia, around 1886, and he became the inspector-in-chief of export grain for the Norfolk and Western Railroad Company. He held that position until 1898, when he became postmaster of Norfolk. He died there of “chronic nephritis” on February 16, 1903.