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This paper aims to re-visit W. B. Yeats’s elegies of Major Robert Gregory, with an emphasis on his complex attitude toward Gregory’s tragic death during the First World War. Although “In Memory of Major Robert Gregory” has been celebrated as one of the most accomplished elegies composed by Yeats, the poem’s apparently high praise of the deceased and deep sense of loss are tinged with doubts about the validity of Gregory’s rash, impulsive decisions that led ultimately to his death. Yeats’s ambivalence can be further detected in “Shepherd and Goatherd” and “An Irish Airman Foresees his Death,” two poems that deploy formal experiments and thereby express the poet’s unresolved feelings about Gregory’s death. In “Shepherd and Goatherd,” Yeats refuses to mention details regarding the problematic death, focusing instead on the therapeutic effects of poetry in a somewhat generalized way. In “An Irish Airman Foresees his Death,” the poet foregrounds a speaker immersed in Nietzschean tragic joy before his imminent death, but he simultaneously reveals the total absence of the speaker’s clear motivation for fighting on behalf of the British Army. Yeats’s ambivalence about the First World War, which is partially due to his Anglo-Irish identity, leads to his dialectical worldview that rarely leans toward an extreme conclusion.