In 1942, shortly after the Japanese attack on Pearl Harbor, John Cipolla saw a recruiting poster for the airborne infantry outside of the recruiting office in his Rochester, NY neighborhood and signed up. After months of grueling training, he shipped out for Europe with the newly-formed 101st Airborne Division. The year he spent in Europe would be the most momentous year of his life. He took part in Operation Overlord, parachuting into Normandy in the early morning of June 6, 1944, before troops hit the beaches, and parachuted into Holland for Operation Market Garden. He was with the 101st at Bastogne, when they shivered in the snow and fought desperately to keep the Germans who surrounded them at bay. John Cipolla ultimately earned multiple Purple Hearts and a Bronze Star.

Returning to his home in Rochester, he became a lab technician in the electroplating industry until he retired.