Major Kenneth D. Bailey was born in Pawnee, Oklahoma. Later his family moved to Danville, Illinois. He spent three years in the 130th Infantry Regiment, Illinois Army National Guard prior to receiving an appointment to Second Lieutenant in the US Marine Corps, 1 July 1935.
In August 1942 on Tulagi, Solomon Islands, he led a Raider Battalion Company in an assault against an enemy machinegun nest and was wounded. On Guadalcanal his company repulsed an enemy attack on Edson's Ridge 12-14 September 1942 and on 26 September 1942 he was killed in action while leading an attack against Japanese forces on Guadalcanal. For his service in the Solomon Islands he was awarded the Medal of Honor, Silver Star Medal and Purple Heart.