Traditional interpretations of Cao Cao's Short-Song Ballad: Singing to Wine, influenced by his image in Song and Yuan narratives and a contextual criticism framework, often regard the poem as an expression of his yearning for talented individuals and frustration over unfulfilled ambitions. However, such readings fail to address three critical dimensions: first, the "intertextuality" embedded within the poem; second, the emotional divergence between the poetic and real -world spaces; and third, the impact of Confucian thought on shaping aristocratic personalities during the late Eastern Han Dynasty. These omissions dissolve the emotional contradictions and tensions within the text. Short-Song Ballad: Singing to Wine essentially reflects Cao Cao's attachment to the ethos of the scholar-official class. Internally, the poem conveys Cao Cao's pursuit of a stable social and ethical structure and his disillusionment with the absence of a "wise ruler" in the real world. Externally, the thematic coherence across the poem series and the influence of the "wandering immortal poetry" tradition highlight Cao Cao's aspiration for the scholar-official identity.