This chapter investigates whether literature that engages with politics is, or indeed should be, political, and in precisely what sense. It discusses the difference between poetry that is profoundly political—dealing with fundamental moral issues—and simple verse propaganda. It also asks whether freedom is/should be a political concept or if it is something more personal, reaching much deeper into our nature. Looking at several effects of political realities on the artistic process, the chapter argues for the necessity to address the larger, and timeless issues such as suffering, hope, and love, rather than adopting a partisan politics in one’s literary work. In portraying the effects of turbulent politics on individual lives, literature has a unique opportunity to ponder and celebrate our humanity. It can counteract the manipulative language of propaganda, by drawing on the rich resources of a language that, through moments of political upheaval, is able to sustain, if those values which sustain can clearly be articulated.