In the Vietnam War he served with various detachments conducting night raids and training irregular Vietnamese and Cambodian forces for attacks along the Ho Chi Minh Trail.

By the end of the Vietnam War, he was serving as the command sergeant major of MACV-SOG, an elite covert operations unit, where he conducted the first combat high altitude-low opening (HALO) parachute jump in military history.

Waugh retired from the CIA in 2005 and died in 2023; his cremated remains were scattered in a HALO jump over Raeford Drop Zone, North Carolina.

Knowing that it was unlikely that he would be admitted in Texas because of his young age, Waugh devised a plan to hitchhike to Los Angeles, where he believed a person had to only be 16 to enlist.

[1] Waugh enlisted in the United States Army in 1948, completing basic training at Fort Ord, California, in August of that year.

[4] He spent much of 1965 and 1966 recuperating at Walter Reed Hospital in Washington, D.C., eventually returning to duty with 5th Special Forces Group in 1966.

Waugh held this Command Sergeant Major role during the covert unit's transition and name change to Task Force One Advisory Element (TF1AE).

Waugh conducted the first combat High Altitude, Low Opening (HALO) jump,[5] a parachuting maneuver designed for rapid, undetected insertion into hostile territory.

In October 1970, his team made a practice Combat Infiltration into the NVA-owned War Zone D, in South Vietnam, for reassembly training, etc.

He took part in several important assignments in Khartoum, Sudan during the early 1990s, where he performed surveillance and intelligence gathering on terrorist leaders Carlos the Jackal and Osama bin Laden alongside Cofer Black.

Before he took the offer, he decided to further his education, earning bachelor's degrees in Business and Police Science from Wayland Baptist University in 1987.