Pless died in a motorcycle accident on July 20, 1969, just over six months after receiving the nation's highest award for gallantry in action. While driving across a drawbridge which connected the city of Pensacola to Pensacola Beach, his motorcycle plunged off the end of the open bridge into the water. The center span of the bridge opened horizontally, and Pless did not realize it was open until it was too late. His body was recovered by divers seven hours later. News of his death was overshadowed by the Apollo 11 moon landing, which occurred the same day.