In the 11th and the 12th centuries two voluminous biographical dictionaries, the Tarikh Baghdad by al-Khatib al-Baghdadi and the Tarikh Madinat Dimashq by Ibn Asakir respectively, made clear connections between the geographical imagination and questions of political loyalty and religious belonging among the ulama of those periods. While the cities evoked in both titles acted as the organizing principle for the selection of biographical entries to be included, they – and the regions in which they were located – should also be seen as objects of representation themselves in the introductions to the two works. In this paper, I will compare the representations of Baghdad and Iraq on the one hand and Damascus and Syria on the other to illuminate the discursive strategies employed by the authors to endow geographical space with particular political and religious meanings. What this comparison reveals is that the representation of geographical space cannot be reduced to a gesture of local pride or a formulaic convention of the genre but needs to be read, rather, as part of a carefully conceived discourse that allowed the authors to express loyalty and belonging particular to their historical contexts in evocative and compelling ways. Among the contrasts to be explored in this paper are: Syria as a territory of the Bible vs. Iraq as a territory of the Hadith; Iraq as the center of the wordly world (surrat al-dunya) vs. Syria as the holy land (al-ard al-muqaddasa); Damascus as a landscape of mosques and mazarat vs. Baghdad as a landscape of palaces and iqtaat. Among the similarities: both cities are linked closely to, and sometimes interchangeable with, their regions; both cities and regions are represented as threatened by wrong belief; both cities and regions have the capacity to attract the human capital of Islam; and both cities and regions act as foils to each other, and to other territories. By interpreting such contrasts and similarities as the products of discursive strategies and situating them within their historical contexts, I argue that the authors were tapping the geographical imagination selectively to articulate a language of loyalty and belonging appropriate to the challenges they perceived themselves to be facing in their respective periods. In other words, I engage the introductions to the Tarikh Baghdad and the Tarikh Madinat Dimashq as significant intellectual contributions to a politics of place in medieval Islamdom.