Sixth-grade students are challenged in understanding social studies content relevant to particular contexts, then connecting the content and context to their contemporary lives while communicating new knowledge to peers and teachers. Using political cartoons published after September 11, 2001, one sixth-grade social studies teacher designed probing questions and developed meaningful learning experiences relating historical events to current concerns of the students supplementing their curriculum and textbook. Through verbal and written interactions, the students demonstrated in-depth understanding of September 11, 2001, and consequential global ramifications. Subsequently, this teacher used the same strategy to engage learners in additional historical events effectively integrating social studies and literacy to introduce conflict analysis, increase critical thinking, expand text connections, and enhance literacy skills. (Contains 4 online resources.)