James Robert Oliver was born around 1840 in Maryland to James and Eveline Oliver. His father was a farmer who owned $1,000 of real estate and $3,000 of personal property by 1860. He grew up and attended school in Hill Top, Maryland.
He sided with the Confederacy during the Civil War, and he enlisted in the Confederate army in Richmond, Virginia, on April 20, 1862. He mustered in as a private in Company K of the 1st Maryland Cavalry later that day. According to his service records, he was 5 feet, 10 inches tall, with dark hair and gray eyes. The regiment took part in the Peninsula campaign.
Union forces captured him in Virginia on February 24, 1863. A military commission tried him for treason in May 1863, noting that, although he was a “citizen of Maryland,” he was “taken prisoner while in arms in the ranks and uniform of the rebel army.” He pled “guilty to the specification, but not guilty to the charge.” The court found him guilty and sentenced him to be hanged, but President Abraham Lincoln spared his life. He was exchanged on February 26, 1863. He was wounded again near Meadow Bridge, Virginia, on May 12, 1864, but he eventually recovered. He was promoted to corporal on February 15, 1864, and to 1st lieutenant on January 15, 1865. Union forces captured him again at the end of the war, and he received his parole on May 12, 1865.
He returned to Maryland after the war, and he married a woman named Nina around 1868. They had at least four children: Edward, born around 1869; Herbert, born around 1873; Anna, born around 1877; and Jennie, born around 1879. They lived in Baltimore, Maryland, and he worked as an editor. He died sometime after 1914.