James was born on the 28th of October 1871, in Rye Cove, Virginia, and unfortunately not much is listed about his life. I found record of his mother, Emily, and a brother, John, but that is about it. He did enlist in the US Army from his home town and by the time he deployed to the Philippines, he was a Corporal with Company A, 36th Infantry, US Volunteers, and his actions near the town of Porac, with the assistance of Cornelius Leahy, later earned him the Medal of Honor. The citation reads:

While on a scout drove off a superior force of insurgents and with the assistance of one comrade brought from the field of action the bodies of two comrades, one killed and the other severely wounded.

James returned home to the States and was married to Nannie, with whom they had one son. He received the Medal of Honor on the 1st of March 1902, and on the 19th of January 1946, James Robert Lee Gillenwater died at the age of 74. He was originally buried in Payne Cemetery in Rogersville, Tennessee, but now rests with his wife in the Highland Cemetery in Rogersville: Section 3.