Undergraduate students often struggle with understanding the theories of Bourdieu, but they are essential for understanding how power and privilege are reproduced in society. Revealing students' complicity in this system is a powerful teaching moment, but it is often difficult to make the lesson and advanced theory accessible without triggering students' defense mechanisms. Discussions of oppression often generate reactions of resistance, paralysis, and rage. This article describes a simulation designed to thwart student passivity while also being cognizant of pushing students too far emotionally. By having students adopt an identity during play and then analyze the results of their simulation, students were able to identify with structural oppression and learn Bourdieu's principles of cultural capital and reproduction.