He was sent to Alcatraz Island in 1959 and given prisoner number #AZ 1403. On the evening of December 16, 1962, the 35-year-old tried to escape from the island, together with 31-year-old Darl Lee Parker (inmate #1413-AZ), a convicted bank robber and hijacker who was sentenced to 50 years. While working on culinary duty in a storage room below the kitchen, the two bent the bars of a window in the latrine of the cell block, climbed down a rope, and made it to the water. They then attempted to float to the San Francisco shore, a distance of 1.4 miles. For that purpose, they made water wings from stolen rubber gloves which they blew up. The escape was noticed at 5:47 a.m. Parker had to give up after a short time because he had broken his ankle during the escape. He was recaptured twenty minutes after the escape was discovered, on the rock formation Little Alcatraz, which lies 100 yards from Alcatraz Island.