In Chile, some elite private schools have developed a particular approach towards citizenship education, acknowledging the privileged social position their students occupy, while inviting them to disrupt the same social structure that has produced this privilege. However, the enduring salience of Chilean society's inequalities begs the question of how effective this approach truly is. This paper attempts to answer this, examining a Chilean private school and a particular service-learning activity. Through ethnographic methods and an analysis rooted in cultural production theory, the paper argues that, although many of its components are still quite problematic, service-learning activities like this one do provide opportunities for promoting participatory and social justice citizenship education, through the students' engagement in "collective deliberations." However, these opportunities are neutralized when framed within a particular cultural fact--here called the Discourse of the Leaders--which displaces the enactment of students' citizenship into a future that still does not exist. The article provides a more nuanced understanding of the different ways inequitable social structures of privilege are dealt with in elite educational institutions that explicitly purport to challenge them. It also offers new avenues for educators to contribute to citizenship education practices that can more effectively promote social change.