Examining history from the perspective of investigators who wrestle with involved scenarios for which no simple answers exist, or from which no obvious conclusions can be drawn, allows students to understand the historiographic process and the complex nature of historical events, while gaining valuable practice in applying analytical and critical thinking skills. This paper provides a lesson plan that illustrates the application of such higher-order thinking processes to a specific historical topic. The goal of this lesson plan is two-fold: (1) to provide students with factual knowledge about Jewish emigration from Germany during the Nazi era; and (2) to complicate student thinking about that emigration, thus fostering analytical and critical thinking processes that will allow students to consider historical events in increasingly sophisticated ways. This lesson plan asks students to evaluate the decision to stay or leave Germany from the perspective of German Jews (or Jewish Germans) who were faced with what became, in time, a matter of life or death. (Contains 19 resources and 63 notes.)