Thomas W. Dees was born around 1842 in Neshoba County, Mississippi, to Thomas and Delia Ann Dees. His father was a farmer who owned $50 of personal property by 1850. He grew up and attended school in Neshoba, and by 1860, he was working on his father’s farm.
He enlisted in the Confederate army on May 29, 1861, and he mustered in as a private in Company D of the 14th Mississippi Infantry. According to his service records, he was 5 feet, 8 inches tall, with dark hair and dark eyes. He fell ill in early 1862, and he was discharged on March 27, 1862. He returned to the Confederate army in August 1862, mustering in as a private in Company G of the 40th Mississippi Infantry. He was severely wounded during the siege of Vicksburg, and he died on May 30, 1863.