In his book Ibn Khaldun’s Philosophy of History, Muhsin Mahdi identifies Ibn Khaldun with the figure of the philosopher in Ibn B?jja’s Regime of the Solitary, a lonely rational investigator (f??i?) constantly in flight from ideological opponents and easily manipulated mobs. This image of the solitary philosopher was once identified as the appropriate metonymy for the condition of Islamic philosophy, allegedly a short-lived project stifled by the intransigence of Islamic religious thought and cultural incompatibility. This narrative has been largely debunked by modern scholarship but the question of the difficulty of the philosophical pursuit still looms in the background. This paper takes up the example of Ibn Khaldun’s status as an alienated historian and lonely rational investigator through his autobiography (al-Ta?r?f b? Ibn Khald?n wa ri?latihi gharban wa sharqan) as well as his reception in contemporary Tunisian fiction, in which his solitariness is repurposed. It aims to explore how in Ibn Khaldun’s self-narrative as well as in his afterlife in the fictional worlds of Hussein El-Wad’s and Kamel Riahi, political power, rather than cultural incompatibility, emerges as the limit experience of the philosophical pursuit (in the Foucauldian sense of the experience of both the condition of the intensification of something and its impossibility). In Ibn Khaldun’s autobiography and modern Tunisian texts, the political, rather than the cultural, represents the site of hope for philosophical thought as well as its alienating betrayal. Ibn Khaldun conceived of history as the locus of rational and moral education that can help political elites found and maintain prosperous polities. He devoted his career to this pedagogical role. His hopes were often undermined by short-sighted political expediencies forcing him into a life of constant exile. This life of ambition and disenchantment with power is taken up by the aforementioned authors, rendering Ibn Khaldun a morose critic of the irrationalities of the neoliberal state and its betrayal of its population. This paper investigates, then, the interplay between the philosophical and the political in Ibn Khaldun’s life and his cultural afterlife.