After retiring from the Richmond police force in 1955, Dey began painting illustrations of stories and scenes from his life. Neighborhood children nicknamed him "Uncle Jack," which he used to sign all his artwork. Preferring bright colors, he painted with unmixed Testor's model-airplane enamel. Even in his most serious religious paintings, Dey added a dash of his dry humor.
Lynda Roscoe Hartigan Made with Passion: The Hemphill Folk Art Collection in the National Museum of American Art (Washington, D.C. and London: National Museum of American Art with the Smithsonian Institution Press, 1990)
John William Dey grew up in Richmond, Virginia, but traveled to Maine as a young man to work as a trapper and logger. In the mid-1930s he returned to Richmond, where he eventually joined the police force. He was "on the beat" for almost thirteen years and earned the nickname "Uncle Jack" from the neighborhood children, whose toys and bicycles he often fixed (Chuck and Jan Rosenak, Museum of American Folk Art Encyclopedia, 1990). He started to paint after retiring from the police, using model airplane paint to create images inspired by childhood adventures, religion, and imagined exotic landscapes.