In this article, I argue for the importance of conducting comparative studies of educational interventions implemented within the same sociopolitical environment. Taking into account both arguments for comparative research in education and recent calls for context-rich vertical case studies, I suggest that horizontal comparisons in a single environment provide a nuanced view of divergent programmatic approaches and outcomes and allow us to better understand the agency of actors in the educational realm. I draw on the concept of multilevel opportunity structure to explore the work of two encounter organizations in Israel bringing together Jewish and Palestinian youth--Peace Child Israel and Sadaka Reut--and explain why the responses of each organization to shifting political environments in the Israeli context over the past 30 years, especially post-2000, led to different outcomes in terms of organizational survival. My analysis demonstrates how methodological choices affect the potential for theory building in comparative education and points to the importance of examining educational initiatives at an organizational level in order to better understand the relationship between educational initiatives and the broader sociopolitical context.