When he was eleven, Robertson was enrolled in the preparatory McDonogh School outside Baltimore, Maryland. From 1940 until 1946 he attended The McCallie School in Chattanooga, Tennessee, where he graduated with honors. He gained admission to Washington and Lee University, where he received a B.A. in History, graduating magna cum laude. He joined Sigma Alpha Epsilon fraternity. Robertson has said, “Although I worked hard at my studies, my real major centered around lovely young ladies who attended the nearby girls schools.”
Robertson has described his military service as follows: “We did long, grueling marches to toughen the men, plus refresher training in firearms and bayonet combat.” In the same year, he transferred to Korea, “I ended up at the headquarters command of the First Marine Division,” says Robertson. “The Division was in combat in the hot and dusty, then bitterly cold portion of North Korea just above the 38th Parallel later identified as the ‘Punchbowl’ and ‘Heartbreak Ridge.’ For that service in the Korean War, the Marine Corps awarded me three battle stars for ‘action against the enemy.'”
Parts of Robertson’s description of his service were later proven to be false. Former Republican Congressman Paul “Pete” McCloskey, Jr., who served with Robertson in Korea, wrote a public letter that said that Robertson was actually spared combat duty when his powerful father, a U.S. Senator, intervened on his behalf, and that Robertson spent most of his time in an office in Japan. According to McCloskey, his time in the service was not in combat, but as the “liquor officer” responsible for keeping the officers’ clubs supplied with alcohol. Robertson filed a $35 million libel suit against McCloskey in 1986. He dropped the case in 1988, before it came to trial and paid McCloskey’s court costs. According to a newspaper report from 1986, Robertson confirmed elements of McCloskey’s allegations and said that he never saw front-line duty.