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James Toler graduated from Minonk High School in 1943 where he played baseball and basketball and participated in track and the chorus.

Two weeks after graduation, he enlisted iand took his basic training at Keesler Field in Mississippi. In August 1943, he was sent to Sheppard Field, Texas, where he graduated as an aviation mechanic and technician on 28 January 1944. He was then transferred to Inglewood, California, for six weeks of advanced training with the North American Aircraft Company. On 14 March 1944 he entered gunnery school in Fort Myers, Florida and graduated on 5 May 1944. He was sent overseas in October 1944.

The last letter to reach his parents was dated 25 December 1944, just five days before his last mission. In that letter, he stated he had completed eight missions. He was on his tenth mission when he lost his life.

Aircraft 42-97400 and 43-38473 collided at 1302 hours at 5055N-0910E at 26,300 feet in the vicinity of I.P. A/C 73 flying in No. 2 position of low section, lead squadron, and A/C 400 flying #4 of low section lead squadron. A/C 473 lost altitude, and #400 gained altitude at the same time. The reason for this is unknown, but it is believed that prop wash was responsible. A/C 400 had its fuselage cut in two and went into clouds in an uncontrolled spin. Elevators on A/C 473 were sheared off, and it, too, disappeared into the clouds out of control. No chutes were observed from either plane. All crewmembers were killed in action.