In her classic essay on a set of controversies in the life of the distinguished al-Khatib al-Baghdadi (d. 463/1071), Fedwa Malti-Douglas (1977) drew attention to the ways in which biographical dictionaries were not only repositories of prosopographical data, but also literary artefacts reflecting particular textual strategies that shape the narrative. More recently, this kind of analysis was extended further in the monograph by Michael Cooperson (2000) on the various biographical representations of four distinct figures from the time of al-Ma'mun, including the caliph himself. A key member of al-Ma'mun’s court, the chief judge Yahya b. Aktham (d. 242/857) offers a further useful test case for studying how medieval Muslims authors chose and interpreted the biographical material on a distant historical figure. For Cooperson, Ibn Aktham’s religious credentials and his relationship to the caliph proved strategically useful for a Sunni “remaking” of al-Ma'mun. But that still leaves unresolved the problems with Ibn Aktham himself, foremost among which were the accusations of liwat and related immoral conduct. A review of Ibn Aktham’s representation in the sources and their treatment of the various aspects of his life thus allows us to explore key questions about Arabic biographical literature. In particular, the topic of the scandal alone reveals a striking divergence between the tabaqat and the accounts appearing in other belletristic/adab sources—thus in a way supporting Wadad al-Qadi’s (2006) appraisal of the genre as an “alternative history” by the 'ulama. Taking a diachronic view starting with the first extensive and complicated biography of Yahya b. Aktham by none other than al-Khatib al-Baghdadi, this paper investigates whether and how the subject’s theological identity affects the perception of details reported about his personal life. In Ibn Aktham’s case, the fact that he was left untainted by the Mihna (having ceded his position to the Mu'tazili chief judge Ibn Abi Du'ad) and enjoyed the support of Ahmad b. Hanbal, became a crucial detail that helped manage his reputation. However, an interesting shift would occur such that later medieval biographers like al-Dhahabi (d. 748/1348) and Mughaltay (d. 762/1361), would impose a logic of personality on the narrative of Ibn Aktham’s life, to explain what even gets labelled as youthful indiscretions. Following the course of this development reveals how over time individual authors could both work within the tradition but also depart from it.