Robert George Cole was born on March 19, 1915 at Fort Sam Houston, San Antonio, Texas. His father was a doctor in the United States Army. Cole himself enlisted in the Army on July 1, 1934 and was honorably discharged about one year later to become a cadet at the United States Military Academy, West Point.
Cole graduated West Point with the class of 1939 and was commissioned as a Second Lieutenant in the infantry branch. In early 1941, he volunteered for the nascent airborne force, and earned his parachute jump wings in March of that year. With the United States’ entry into World War II, advancement in the airborne was rapid.