Barry McCaffrey was born on November 17, 1942, in Taunton, Massachusetts. He entered the U.S. Military Academy at West Point in 1960, and graduated with a commission as a 2d Lt of Infantry in the U.S. Army on June 3, 1964. After completing jump school and Ranger school, Lt McCaffrey was assigned to 2nd Battalion, 325th Infantry, of the 82nd Airborne Division at Fort Bragg, North Carolina, until deploying to Southeast Asia in 1966. While stationed with the 82nd Airborne, he participated in the Invasion of the Dominican Republic in 1965. He served with U.S. Military Assistance Command Vietnam in Saigon, Republic of Vietnam, from 1966 to 1967, and then with U.S. Army South at Fort Amador, Panama Canal Zone, before returning to South Vietnam, where he served with the 2nd Battalion, 7th Cavalry, of the 1st Cavalry Division from 1968 to 1969. Capt McCaffrey then served with Headquarters U.S. Army in the Pentagon, followed by service as an instructor with the U.S. Armor School at Fort Knox, Kentucky. He was an instructor at the U.S. Military Academy from August 1972 to July 1975, followed by service with the 3rd Infantry Division in West Germany until June 1981. After completing Army War College, McCaffrey commanded the 3rd Brigade of the 9th Infantry Division at Fort Lewis, Washington, and then served as assistant commandant of the U.S. Army Infantry School at Fort Benning, Georgia. He then served as Deputy U.S. Representative to NATO in Brussels, Belgium, from January 1988 to July 1989, followed by another tour at the Pentagon as Deputy Chief of Staff for Operations & Plans with Headquarters U.S. Army. Gen McCaffrey served as commander of the 24th Infantry Division (Mechanized) at Fort Stewart, Georgia, from March 1991 to May 1992. During this time, he deployed with the Division to Saudi Arabia and participated in Desert Shield and Desert Storm. His next assignment was as Director for the Strategic Plans and Policy Directorate on the Joint Staff from June 1992 to February 1994, followed by service as commander of U.S. Southern Command in Panama, from February 1994 until his retirement from the Army on February 29, 1996. After his retirement from the Army, Barry McCaffrey was the 4th Director of the Office of National Drug Control Policy from February 1996 to January 2001.

His 2nd Distinguished Service Cross Citation reads:

For extraordinary heroism in connection with military operations involving conflict with an armed hostile force in the Republic of Vietnam: Captain McCaffrey distinguished himself by exceptionally valorous actions on 9 March 1969 as company commander during a reconnaissance-in-force mission. When elements of one of his platoons came under intense fire from a well-fortified enemy bunker complex, Captain McCaffrey immediately moved forward to assault the hostile position in order to relieve pressure on the beleaguered squad. He quickly deployed his men for an attack and led the advance through the fusillade. When he had pinpointed the source of the greatest concentration of fire, he initiated a single-handed assault on the bunker. After several attempts, he finally succeeded in destroying the machine gun bunker and its occupants. Despite being wounded in the left arm, he continued to supervise the overrunning and destruction of the hostile bunker system. After organizing the evacuation of his casualties, he called in supporting fire on the enemy. Only after he was assured that all of the wounded had been cared for and after he had organized a defensive position, did he allow himself to be evacuated for medical treatment. Captain McCaffrey's extraordinary heroism and devotion to duty were in keeping with the highest traditions of the military service and reflect great credit upon himself, his unit, and the United States Army.