September 11, 2001, was a critical teachable moment that provided the author of this article and his team with an avenue to middle level curriculum that was relevant, challenging, integrative, and exploratory. Hurricane Katrina opened a similar window of opportunity for middle level educators to focus the minds of young adolescents on important issues that are meaningful to everyone. However, developing curriculum around events and issues like these requires a unique curricular process that allows teachers to plan in real-time as events unfold and issues become salient. Teachers need to adopt a generative approach to curriculum planning that involves responsive and reflective practices. In this article, the author draws upon his experiences as a seventh grade teacher during and after the terrorist attacks of September 2001 and as a middle level teacher-educator during the aftermath of Hurricane Katrina in September 2005 to describe this curricular process. (Contains 2 figures.)