Democracy and capitalism are two of the most consequential institutional systems in the world. However, their dynamic complexity, current turmoil, and evolution make them challenging to study. High-engagement teaching can bring the subjects alive, motivate student exploration, inform choices, animate sensible policy recommendations, and make a deep impression capable of recall well after the course. In this article, the author reviews why teaching about democracy and capitalism can be challenging, how high-engagement teaching can respond to the challenges, and what kinds of strategies and materials can promote high engagement. Case studies afford excellent opportunities for high-engagement instruction and for doing economic analysis in realistic contexts. The article concludes with a review of examples of cases that focus on data analysis and decision-making.