Born in Chicago, Illinois, and received his high school education in La Jolla, California, and two years of technical training at the General Motors Institute of Technology in Flint, Michigan.

His military training included: Spartan School of Aeronautics, Tulsa, Oklahoma; Basic Flying, Randolph Field, Texas; Advanced Flying Kelly Field,[1] Texas; Bomb Commander Training, Sandia Base, New Mexico; and, Radar Bombing Indoctrination, Mather AFB, California.

He was assigned duty as commanding officer of the Air Transport Unit during Operation Crossroads (Bikini Atoll - Atomic Bomb Test) and served overseas from May 6 to August 19, 1945.

[9] Apparently, wreckage had been found the previous week by a local rancher, and once General Roger M. Ramey[10] was informed, he ordered it be flown to Fort Worth Army Air Field.

On July 13 following the first major strike of the Korean War,[14][15] Jennings, in order to obtain visual reconnaissance of the destroyed Wonsan Oil Refinery, went in alone in a B-29 under a 400 ft. ceiling in the rain at 280 mph.

During the initial three months of the war, the 19th performed at an intense and exceptional level of operations where the 19th continued to fly at the highest possible sortie rate that could be sustained on a seven-day week.

The Group flew its 128th mission on Christmas Day since the advent of hostilities on June 25 and without a single replacement since the war started.

[20] Apparently his B-29, #1749, lost two engines in an attempt to salvo the Tarzon Bomb at a very low altitude over the ocean, resulting in a premature detonation that took their aircraft down.