Insurance is an interesting interdisciplinary topic that can offer generative meaning and relevance for students. By adapting real life examples and authentic simulations, mathematical concepts can be applied to insurance-related social studies issues and content. This article explores ways to teach insurance and related mathematical concepts to middle school students using an interdisciplinary approach and it demonstrates various concomitant benefits in teaching mathematics with the concept of insurance by connecting it to important democratic citizenship dispositions such as civic participation, critical thinking, interpersonal skills, and knowledge of political activity. The ultimate goal of this interdisciplinary approach is to develop students' ability to make informed and reasoned decisions as current and future consumer-citizens.