The primary focus of this study is the figure of Trypho in Justin Martyr's 'Dialogue with Trypho, A Jew' (mid-second century C.E.). A close-reading of Trypho's character reveals a consistent figure who does not appear to be based on a Jewish stereotype or Christian invention. Instead, he is a pre-rabbinic Diaspora Jew whose argumentation style is philosophical, even Socratic. By listening to Trypho one can hear a voice with its own sensibility, style and agenda. It is a voice which defies fiction. This work also forwards the hypothesis that within the Dialogue there is a free-standing text comprised almost exclusively of dialogue material. This work provides evidence that the 'Trypho Text' was once the core of the original dialogue (ca. 135-137 C.E.). This investigation of Trypho is important for our understanding of early Christianity, second-century Judaism, and the relationship between them.