In his very well-known essay “The Task of Translator,” an introduction to a translation of The Tableaux Parisiens of Baudelaire, Walter Benjamin regarded translation as a work of art that should be fully appreciated. The task of the translation should not be viewed within a narrow prism whereby translation is an instrument conveying information from the source text to the target text. Rather, it is a process that adds originality and gives new life to the source text. Benjamin contended that “a real translation is transparent; it does not cover the original, does not block its light, but allows the pure language, as though reinforced by its own medium, to shine upon the original all the more fully.” Benjamin, in his theorization of translation, addressed the main critiques staged against translation, and in his defense of the translator, he wrote that “the task of the translator consists in finding that intended effect upon the language into which he is translating which produces in it the echo of the original.” Similarly, Damrosch, in his book How to Read World Literature, reiterated the same idea when he stated that “When it is read intelligently, an excellent translation can be seen as an expansive transformation of the original, a concrete manifestation of cultural exchange, and a new stage in a work’s life as it moves from its first home out into the world.” These views of literary translation bespeak the creativity involved in the art of translation. The paper examines the English translation of Wafai Laila’s and Akram Alkatreb’s war poetry, focusing on how war, loss, displacement, and grief, among other, have inevitably affected the subjectivities of these two Syrian poets and been conceptualized in their artistic productions, in particular their poetry.