While attending Yale, Bennett went to Canada to join the Royal Flying Corps in October 1917. He was fond of shooting down balloons. During his brief but remarkable nine day career, Bennett flew 25 sorties and shot down nine enemy balloons piloting an S.E.5a. On August 24, 1918, after destroying his last two balloons, his aircraft burst into flames when it was hit by ground fire. He was captured and taken to an aid station where he died from his injuries.