This chapter argues that reading Chelsea Manning as an outsider truth-teller, and developing a defense of outsider truth-telling, is important to our understanding of the relationship between democracy and truth more generally. Outsider truth-telling reveals problems with, and offers an important alternative to, our dominant understanding of truth and democracy, namely, that democracy is dependent on truth because it offers prepolitical stability for a society of diverse viewpoints. The chapter argues that this dominant view actually grew out of particular historical circumstances and is tied to a raced, classed, and gendered conception of truth-telling. In this context, outsider truth-tellers should be understood as crucial yet vulnerable figures in democracy, revealing from a position of social illegibility an unsettling reality that their societies need to see. This chapter calls democratic theorists to raise, thematize, and address, as central concerns for democracy, the predicaments and problems surrounding outsider truth-telling.