James Dearing was born on April 25, 1840, at ""Otterburne"" near Altavista, Virginia. When his father died in 1843, Dearing was adopted by his uncle. In 1858, after graduating from Hanover Academy, a classical school near Richmond, Dearing entered the United States Military Academy.

In 1861, Dearing left West Peint to join the Confederate Army. He joined the Washington Artillery as second lieutenant and, in July, 1861, distinguished himself at the First Manassas. By April, 1862, he was a captain. With that rank, he fought in the Peninsula campaigns at the Second Manassas. Early in 1863, as mayor, Dearing received command of General George Pickett's artillery. Impressed by Dearing's ability at Gettysburg, Pickett transferred him to the cavalry and recommended his promotion to lieutenant colonel.

In April, 1864, Dearing’s cavalry overwhelmed the Federals at Plymouth, North Carolina, earning Dearing a promotion to brigadier general. The Confederate attack against New Bern was interrupted when Dearing was ordered to Petersburg. For nine months Dearing defended Petersburg and its vital railroads.

Early in 1865, Robert E. Lee gave Dearing command of the Laurel Brigade and recommended his promotion to major general. Before receiving the promotion, Deairing was mortally wounded near Farmville while covering Lee’s retreat toward Appomattox.

On April 22, Dearing died at Lynchburg. He was buried at ""Avoca'' near Altavista. His body was later disinterred and reburied at Spring Hill Cemetery, Lynchburg.

In March, 1863, Dearing had married Roxana Birchett. The couple had one child, Mary Lucretia.