Lillian was a "Grandmother" to him and knew how to make the most of a difficult situation, living in a shack home. Everything was segregated in rural Georgia and African-Americans were poor and often afraid of being lynched. They had only the comfort and pleasure of friends and church. Rembert had an active imagination and made toys for himself out of wood and glass, bicycle rims, old syrup cans and haywire.

He dropped out of school in the tenth grade. Chopping cotton and shaking peanuts for low wages wasn't for him either. The Civil Rights movement attracted him but led to trouble. When he was arrested in 1967, he was almost lynched, then sentenced to 27 years on a chain gang. Another convict saw Winfred's aptitude and helped him learn how to survey roads, reading blueprints and using the transit, a skill which became valuable to prison officials.

In 1972, Rembert volunteered to help the only convict allowed to do leatherwork, and apprenticed by tooling rose designs on purses and other articles and soon realized that he wanted to create his own leatherwork. He made his tools in the prison auto shop.

Rembert's pictures are first sketched out on paper and then hand tooled on cured leather. The tooling allows for unique depth and textures. After tooling, leather dyes are used to paint the leather, producing the strong colors that characterize his work. He often writes his thoughts about a picture to provide background and context. Rembert says that he has so many pictures waiting in his head that he doubts that he will ever get them all on leather.