Although Arabic literary and historical sources from both ancient and modern times have affirmed Ibn al-Muʽtazz’s (d. 908) inestimable legacy as a scholar in poetics and rhetoric during the height of the Abbasid caliphate (8th – 10th centuries), less scholarly attention has been paid to his political and social attitude that must have been behind a number of disputations that were obscured by his poetry and poetics. Ibn al-Muʽtazz’s longstanding literary fame and distorted readings of his stormy biography have led to a decontextualization of the “fair doomed prince” devoted to belle lettres, neglecting to observe his keen political thought in its historical context. To date, few attempts have been made to pursue an interdisciplinary reading of al-Muʽtazz’s works to paint a comprehensive picture of this unconventional intellectual figure. Ibn al-Mu’tazz is more compelling in light of his comprehensive knowledge of languages of learning (e.g., Greek, Persian), expertise outside of literature and rhetoric (e.g., medical learning), and development of new categories for conceptualizing Arabic literary aesthetics, however, imbued with political and ethical considerations. Using a holistic methodology that draws on Arabic rhetorical analytical tools as well as the sociology of literature, this intervention aims to briefly provide the first critical inquiry into caliph Ibn al-Muʽtazz’s Fuṣūl al-tamāthīl fī tabāshīr al-surūr [Examples and Similes on the Pleasure of Sharing Joy], a small treatise on wine and courtly amusement. Notably, my research investigates al-Muʽtazz’s decision to use the introduction of his charming, brief treatise as the staging ground for his political manifesto. Arguing Fuṣūl as a ʿliterary artifact,ʾ this study explores this work as a stage to vindicate positions polemically or the trench from which it is possible to boost the last mufākharāt about languishing Abbasid caliphate. Merging poetry and wine, Fuṣūl is a unique place where munaẓārāt and nostalgia interact in a very subtle and original way offering a keen insight into ninth-century Abbasid society, culture, and politics.