In the search for Matthean theology, scholars overwhelmingly approach the Gospel by way of Sitz im Leben. Whether arguing from a perspective that Matthew wrote from a cloistered Jewish community, perhaps as the master of a rabbinic-type school, or arguing from the other extreme, that Matthew is writing as the leader of a Gentile rebellion against such a Jewish community, scholarship appears unable to avoid the question of Matthew's and his community's relationship to Judaism. While this is undoubtedly an important and necessary question for understanding the Gospel, it often assumes too much about the relationship between Judaism and Hellenism. Scholars with such a sharp focus on this question tend to neglect Matthew's provenance in a thoroughly Hellenistic culture and first-century Judaism's thorough Hellenization. Part 1 of this dissertation (chapters 2-5) argues for a hybridized perspective in which Matthew's attention to Jewish sources and ideas is not denied, but in which echoes of Greek and Roman sources and ideas from Antiquity can be observed. This argument includes a survey of recent scholarship on the Judaism/Hellenism divide, consideration of several aspects of the Gospel (e.g. language, sources, provenance, genre), a discussion of rhetorical methodologies, and a survey of relevant ancient education practices. In Part 2 of this dissertation (chapters 6-8), I explore two facets of Matthew's Gospel as examples of the kind of Hellenistic contextual reading I am proposing. First, I specifically explore the Sermon on the Mount in the context of ancient Greek historical and philosophical writings (particularly of the Socratics). Second, I explore the possibility of Homeric resonances throughout the Gospels. I conclude that Matthew's Gospel has a rich Greco-Roman backdrop-one that will only help us as we seek to interpret the text of the Gospel and learn how it was understood by its first audience.