This essay looks at the work of children's book author and cartoonist William Steig through the lens of infancy research and theory. Recurrent illustrations in his works portray a character lost or stranded in the midst of an inhospitable and vast empty space. This material may represent this artist's ability to provide a window into early separation experiences. It is suggested that, as an artist, Steig may be creating visual representations of early states of mind pertaining to attachment and separation. In addition, Steig's work seems to graphically illustrate the resiliency of secure attachments as well as the protective function of a theory of mind. Illustrations from Steig's children's books will be used to flesh out these suggested hypotheses.