Richard Cliff, Jr served in the U.S. Army as a Captain Ranger in Company B, 1st Battalion, 7th Special Forces Group (Airborne) in Operation Enduring Freedom. He was Commander, Special Forces Operational Detachment Alpha Team, deployed as a member of the Combined Joint Special Operations Task Force-Afghanistan. He was killed on September 29, 2008 while conducting a combat reconnaissance patrol in the vicinity of Yakhchal, Helmand Province, Afghanistan. He was awarded four Army Commendation Medals, the Army Achievement Medal, the Iraq Campaign Medal, the Combat Infantryman Badge, the Parachutist Badge, and several others.