In different fields of academia today there is renewed interest in the relationship between religion and politics. However, this literature often focuses on beliefs such as extremism and nationalism at the expense of historically contextualized discussion about the organization and practices associated with religion. As analysts observe the ‘retreat’ of the promise of secular modernity, it is easy to be left with little or no grounded understanding of how religious organizations are engaging in spaces of contested politics or how this engagement can help us to understand more appropriately what ‘religion’ or ‘politics’ mean to individuals and communities on personal and organizational levels. Within this broader debate, this paper introduces a research project that explores one form of religious practice: the ability of religious leaders to cross violent or politicized borders in times of contestation and conflict. The empirical focus on the Sri Lankan Catholic Church, in Tamil areas in the north, presents the activity of priests in such circumstances as a form of ‘brokerage’, facilitated and constrained by their religious, institutional setting.