The informant is both a controversial medium of security and a maligned cultural figure. Their actions and stories about their actions are integral nodes in the economy of fear that structures surveillance society. This paper examines how Cold War and war on terror informants tell stories about themselves (Budenz 1947; Speckhard and Shaikh 2014) against the backdrop of a “fear of small numbers” (Appadurai 2006) on the home front. The overlapping intentions (confession, memoir, apology) and I’s (narrated, narrating, and ideological) in their memoirs provide an entry point for assessing how informants assert their authority and how they reproduce the security cultures in which they find themselves. Each memoir draws on ideological pairings central to discourses of infiltration and radicalization, respectively. The authors confess to having been the duped or radicalized westerner but narrate from the position of the patriotic Catholic or “good Muslim.” Ultimately, I argue that the narrative and ideological climax of the memoirs lies in how the transformation from enemy to friend is presented: as the result of a chance encounter. This shifts the fear of small numbers from the one amongst us who might become a traitor to the slim and incalculable probability through which one returns from extremism, which is by definition less than one. Marked as the exception, the narrative reinforces the necessity of the informant in security practices.