O'Leary was the navigator on B-24L #44-49710, assigned to the 15th Air Force, 464th Bombardment Group, 779th Bombardment Squadron. The plane was named Stevenovich II, after the pilot's son.
They were flying from Pantanella Air Base on a bombing mission against Lugo Italy to support ground forces of the the British 8th Army. Right after releasing the bombs the aircraft was hit by anti-aircraft fire on the left wing which caught fire and broke apart. The plane turned over and started tumbling. The radar operator was thrown clear and was able to parachute to the ground where he was taken prisoner. The other ten men aboard were killed.
He received the Air Medal with three Oak Leaf Clusters.
Entered the service from Kentucky.
Sponsored by Ancestry