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Kassal enlisted in January of 1942 and was assigned to the Army Air Forces. He was sent to Camp Upton at Yaphank, Long Island, New York. His first assignments included kitchen duty and handing uniforms to new recruits and draftees. He remembers giving heavyweight fighting champion Joe Lewis his uniform. He was then assigned to Mitchell Field with the quartermaster corps for about five months. He attended OCS [Annotator's Note: Officer Candidate School] at Miami Beach, Florida. He recalls meeting Clark Gable at OCS and women lining up to meet him. Kassal received a commission as a 2nd lieutenant upon graduating OCS; he graduated 14 out of 2,000 men.At that time, the Army Air Force wanted to expand their intelligence units. Kassal was accepted to attend the Army Air Forces intelligence school at Harrisburg, Pennsylvania. He recalls his time in Miami; marching down Collins Avenue and antisubmarine patrols. He attended intelligence school for six weeks. He graduated number four in his class and was given the opportunity to choose his assignment. His first choice was England, second choice was North Africa. Kassal was eventually given an assignment to North Africa and deployed overseas on the SS Dorothea Dix in the fall of 1942. They traveled overseas in a convoy, Kassal's ship was at the end of the convoy. After a few hours at sea, the water pumps on the Dorothea Dix failed and Kassal was sent back to the states.
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