Career
He served as commanding officer of the first American paratroop unit to jump into combat, the 2nd Battalion, 509th Parachute Infantry Regiment, near Oran as part of Operation Torch during World World War World War II His book, We Jumped to Fight, was based on his experience in that operation and was published in 1944. Raff had served as First Captain of Cadets at a small prep school in Winchester, Virginia called the Shenandoah Valley Academy before serving in the Army. Due to the tough training course he gave the paratroopers in the 509th (and his stocky physique), Raff was nicknamed "Little Caesar" by them.
He first saw combat during Operation Torch as the commander of the 509th:
After the war in 1954, Raff would command the 77th Special Forces Group, based at Fort Bragg and is credited by Lieutenant General William Yarborough as the "father" of the then-controversial green beret now routinely worn by United States Army Special Forces.