Bob Jeffrey was born in 1939 in Los Angeles, California. After attaining Eagle Scout, he graduated from Northrop Institute of Technology, and then entered the Aviation Cadet Program of the U.S. Air Force on January 25, 1960. Jeffrey was commissioned a 2d Lt and awarded his pilot wings at Reese AFB, Texas, on May 12, 1961, and then completed F-102 upgrade training at Perrin AFB, Texas. His first assignment was as an F-102 Delta Dagger pilot with the 509th Fighter Interceptor Squadron at Clark AB, in the Philippines, where he served from January 1962 to July 1964. Jeffrey then served with the 497th and then the 433rd Tactical Fighter Squadron at George AFB, California, from July 1964 to December 1965, and then deployed to Southeast Asia at Ubon Royal Thai AFB, Thailand, in December 1965. Capt Jeffrey was forced to eject from his stricken F-4 Phantom II while flying his 1st combat mission on December 20, 1965. After spending 2,611 days in captivity, he was released during Operation Homecoming on February 12, 1973. He was briefly hospitalized to recover from his injuries at Sheppard AFB, Texas, and then entered Southern Methodist University through an Air Force Institute of Technology assignment in August 1973. Col Jeffrey then went through Pilot Instructor Training in November 1976, and served as Operations Officer, Base Exercise Evaluation Team Chief, and Chief of the Operations Division with the 97th Flying Training Squadron of the 82nd Flying Training Wing at Williams AFB, Arizona, until his retirement from the Air Force on January 31, 1980.

His Silver Star Citation reads:

For the Period June 1966: This officer distinguished himself by gallantry and intrepidity in action in connection with military operations against an opposing armed force during the above period while a Prisoner of War in North Vietnam. Ignoring international agreements on treatment of prisoners of war, the enemy resorted to mental and physical cruelties to obtain information, confessions, and propaganda materials. This individual resisted their demands by calling upon his deepest inner strengths in a manner which reflected his devotion to duty and great credit upon himself and the United States Air Force.