Leonard Osborne served in the U.S. Army Air Corps as a Pilot and Second Lieutenant with the 75th Troop Carrier Squadron, 435th Troop Carrier Group during World War II. He was reported missing in action on September 19, 1944 when the C-47A Skytrain (#42-100879) he was co-piloting was shot down over Neuville-en-Condroz, Belgium. A year later, his death was confirmed. The squadron flew its first combat missions on D-Day by dropping paratroopers of the 101st Airborne Division near Cherbourg. They also flew paratroopers on airborne assaults in Southern France and Germany. Lt. Osborne was posthumously awarded the Purple Heart, Silver Star, and Air Medal with Presidential Citation.