The themes of Biblical Studies and mission meet in a significant way at the intersection of the quest for the historical Jesus (an aspect of biblical studies) and the proclamation of the biblical Jesus (an aspect of the mission of the Church). This intersection undoubtedly occurs in the context we currently find ourselves, the evangelical seminary setting. This paper explores a passage, Matthew 4:-11, that has both significant theological content but also some rather difficult historical issues. When confronted with this type of problem, is it possible to navigate the passage in such a way that the historical Jesus and the theological Christ remain recognizable to one another? How can we best teach this passage, and others like it, to our students who will be subsequently be preaching it in their own churches? The hope is that the conclusions set forth in this paper will provide a way forward, but also open up a discussion that will yield even more acute directives for those forced to handle this issue in the future. This paper was presented at the Asbury Advanced Research Program Interdisciplinary Colloquium for 2017 on Biblical Studies and the Mission of the Church.