Academics have raised questions concerning racial imaging in the popular children’s book Curious George. Many of these scholars utilize symbolism to warn readers of hidden messages in the book that negatively affect black children. One of the most prominent images includes the capture of an African monkey by a white man, which academics believe reflects American slave history. These arguments, however, fail to address three important issues this research project emphasizes to properly reinterpret an image. First, one must properly outline a historically racist image such as the American Sambo in order to determine who created the image, what messages are being portrayed by it, and why these messages are important to the image’s creator and audience. Following the outline of a racial image, the next step is to view the rise and fall of another popular children’s book in order to determine how society interprets books over time. The rise in popularity to the outright banning of Helen Bannerman’s The Story of Little Black Sambo in the twentieth century fits this requirement because an extensive academic and social archive detailing the book’s racial debate exists in newspaper articles, editorials, and academic journals. Lastly, this project examines personal and business correspondence of Curious George’s authors, Margret and Hans Rey, and reinterprets the Curious George stories as a mirror of the Reys’ immigration history.