This study examines Ibn Al-Shjari’s syntactic critiques of Al-Mutanabbi’s Diwan in Al-Amali, a 12th-century commentary often overshadowed by lexical and thematic analyses in medieval Arabic scholarship. By analyzing 83 syntactic objections across Ibn Al-Shjari’s work, this article argues that his rejection of darurat al-shiʿr (“poetic necessity”) as a justification for grammatical irregularities reframes Al-Mutanabbi’s ambiguities as deliberate rhetorical innovations. Employing a hybrid methodology of textual analysis and corpus linguistics, the study contrasts Ibn Al-Shjari’s framework with those of Ibn Jinni and Al-Ukbari, revealing his unique integration of classical Arabic grammar (nahw) and rhetoric (balagha). Key findings demonstrate how Ibn Al-Shjari prioritized contextual pragmatics over rigid grammatical norms, particularly in resolving pronominal references (e.g., “He pretends the favor, beginning with it”) and defending Al-Mutanabbi’s defiance of syntactic conventions (e.g., omitting the definite article al- in الفتى). The research underscores Ibn Al-Shjari’s role in bridging grammatical and rhetorical discourse, offering fresh insights into the interplay of syntax and creativity in Abbasid poetry. This study not only reclaims his overlooked contributions but also provides a model for re-evaluating pre-modern Arabic exegetical traditions through interdisciplinary lenses.