A highly nuanced reading of the caliphate and its implications in Mamlūk society emerges from the ground-breaking discourse of the political theoretician and social historian ‘Abd al-Raḥmān Ibn Khaldūn (d. 1406). This paper limits its exploration of Ibn Khaldun’s views to three works: his presentation of norms on the caliphate and secular authority (mulk) expressed in his Muqaddima, the relevant sections of his history Kitāb al-‘ibār, as well as autobiographical recollections in al-Ta‘rīf bi-Ibn Khaldūn wa-riḥlatihi gharban wa-sharqan. While praising the Mamlūks directly in his Kitāb al-‘ibar and indirectly in the Muqaddima, Ibn Khaldūn legitimized their government while subliminally pointing to its flaws in comparison with the classical caliphate. Modern scholarship has characterized Ibn Khaldūn as an outsider and a subdued observer of the practices he witnessed in Mamlūk Egypt. This seems to be the case in regard to his lukewarm approach to the figurehead Abbasid caliphate of his own time. Ibn Khaldūn’s thought expands upon two important themes; the gradual extinction of Abbasid ‘aṣabiyya and the symbolic need for a true caliphate. There is some contradiction in this presentation. As a historian, he flatters the Mamlūks by casting them as rescuers of a corrupt Abbasid dynasty in decline. He likewise projects acceptance of the notion that the Abbasid caliph formally delegates the sultan with all of the caliphal prerogatives. It is thus somewhat unclear if Ibn Khaldūn believed the Mamlūks were sent by God to restore the caliphate, or that they absorbed and remade it in their own image with the Mamlūk sultan as acting imām-caliph. The normative and idealistic tone of the Muqaddima granted Ibn Khaldūn the ambiguity to discuss usurpation of authority without ever naming the Mamlūk sultans as further evidence of a trend. There is certainly a parallel with the other examples that Ibn Khaldūn gives of the sultanate or amirate eroding the authority of the caliphate, but one that he dared not associate with his patrons. This paper also considers the predicament of Ibn Khaldūn as a theoretician reluctant to bite the hand that fed him, in view of points argued by Leo Strauss’s Persecution and the Art of Writing.