Most people have read or heard stories about the American Civil War causing brothers to fight on opposite sides for the North and the South, and about soldiers fighting first on one side and then the other. Well, all this actually happened in our Derryberry family history. Read on to find out the complicated circumstances.

William Derreberry was a farmer and a shoemaker.  When William and his wife Mary (Polly) migrated to Greene County, TN in the 1850s, their two oldest offspring, Susan and Barnabas, were already married and stayed behind in North Carolina. Jefferson, aka Jesse, was also married but chose to travel with the family as did their three youngest sons, James, John and Thomas.  After arriving in Tennessee, James, who is our ancestor, and his brother John married two Garmon sisters in August 1857, one week apart. The marriages took place down the river in neighboring Jefferson County, TN. Then due to an untimely death or some other unknown reason, James got married a second time just a year and a half later to Elizabeth Hansel also in Jefferson County.

In the Spring of 1861, seven southern states seceded from the Union and formed the Confederate States of America. This triggered the War Between the North and the South or the American Civil War. East Tennessee was very divided by the war with people only choosing sides when compelled. William Derreberry and his sons must have had very mixed emotions about the war and perhaps disagreements between family members. None immediately jumped at the chance to go fight. At first the Confederacy relied on volunteer soldiers, but within a year they began conscripting all males between 18 and 35 years of age. This probably caused John Derryberry to be the first in the family to side with the South. In July of 1862, at age 21, he enlisted as a private in the 64th North Carolina Infantry Regiment when it formed in Madison County, NC. Then a month later James Derryberry, at age 23, also enlisted as a private in the 64th when the regiment had reached Sevier County, TN. Since he had learned the shoe making trade from his father, James was put to work making and repairing shoes. Thomas Derryberry was too young to be conscripted.

Poor food, boredom, unhealthy camp conditions, fear of death, and homesickness caused desertion to be a frequent occurrence on both sides. Soldiers close to their homes were especially sensitive to conditions there, and bad news consequently contributed to desertion, particularly among Confederate soldiers.  Being not far from home in Eastern TN, John Derryberry developed a history of desertion.  He first deserted in November 1862, then returned to duty in February 1863 only to desert again in Knoxville in July 1863. Then John totally switched sides and together with his brother, Jesse, joined the Union Army in Greenville, TN. Why did he jump to the side of the Union?  Obviously, he didn’t care for the conditions on the Confederate side, and perhaps his brother Jesse talked him into it. Regardless, they both enlisted on the same day in August 1863 in the 8th Tennessee Cavalry.

John enlisted as a private and went to work as a Blacksmith, and Jesse enlisted as a Corporal, perhaps because at 25 he was older and more mature. Both were described as  5 ft 8 in tall, with John having a dark complexion, dark eyes and hair, and Jesse having a fair complexion with blue eyes and brown hair. They both fought with the 8th Cavalry until the end of the war, and according to records they were mustered out in Sept 1865. However, after the war, John and Jesse  completely disappear from all records. It is highly probable that they both died near the end of the war and their muster out records were incorrectly completed.

Meanwhile, our ancestor, James Derryberry, served for the South with the 64th North Carolina Infantry until Sept 1863. Unfortunately, during his time with that unit, the 64th was involved in one of the greatest atrocities of the war which took place in a remote Appalachian valley of Madison County, North Carolina called Shelton Laurel. In January 1863, under orders from their commander, soldiers from the 64th shot and killed 13 Union sympathizers without any trial or hearing whatsoever. There were many factors that lead up to the Shelton Laurel massacre with grievous errors in judgement on both sides. To learn more, I recommend reading the book Victims A True Story of the Civil War by Phillip Shaw Paludan, which also gives a good depiction of the horrific guerrilla fighting conditions in the mountains. It is unknown whether James Derryberry took part in the actual killings, but probably not as shoe makers typically stayed behind in camp to apply their trade and didn’t normally participate in raids or skirmishes.

By the Fall of 1863, James was detailed to Atlanta to help make and repair shoes at a central location for the Confederacy.  Muster Roll and Pay receipts show that he was “bottoming shoes” and receiving 35 cents per pair. He was then transferred to Major Bridewell’s unit in July 1864. Major Bridewell was the quartermaster for the Confederate clothing depot, which was located outside of Atlanta. General Sherman’s successful siege of Atlanta and march to the sea by Union Forces occurred in late Summer and Fall of 1864. Since there are no further records of James Derryberrry after July 1864, it is strongly believed that he met his death at the hands of Sherman’s troops sometime during that period. He was only 25 years old!