[1] On July 1, 1940, then Cadet Cragg entered what became the first of the World War II accelerated 3-year West Point classes, completing basic flight training by graduation on June 1, 1943.

[1] By V-E Day he had attained the rank of major and had been awarded the Distinguished Flying Cross and the Air Medal with 13 oak leaf clusters.

[1] In the days following the end of the war he met and subsequently married, while still in Germany, his wife, First Lieutenant Helen Claire Petraborg, a nurse with the 91st Evacuation Hospital.

He also served as commander of the 3500th Pilot Training Wing (flying T-37s and T-38s) at Reese AFB outside Lubbock, Texas, which he considered his favorite and most challenging assignment.

Upon his promotion to brigadier general he became deputy chief of staff, operations, the Air Training Command, Randolph AFB Texas.

With the death of his wife Helen in 1972,[8] General Cragg was reassigned to be vice commander of Second Air Force at Barksdale AFB.

[1] His final assignment was as chief of staff of the Allied Air Forces Southern Europe, based in Naples, Italy.

[8] He hunted ducks and geese on Maryland's Eastern Shore; white tail deer, dove, quail and wild turkey in Texas; and pheasants in North Dakota.

[8][9] He died on March 9, 2006[8] and was buried with full military honors alongside his first wife, Helen, in Section 5, Plot 104 Arlington National Cemetery.