The dissertation addresses the lack of in-depth research that thoroughly compares the thoughts of Heidegger and Benjamin. Existing literature is dominated by anecdotal juxtapositions. While Heidegger’s and Benjamin’s works offer numerous potential points of comparison, it has yet to be clarified how these parallels align with Benjamin’s well-known critique of Heidegger. In what follows, I compare Heidegger’s deconstruction with Benjamin’s translation. The research hypothesis posits that both concepts are rooted in phenomenology, particularly in Husserl’s method of phenomenological reduction. While Heidegger’s connection to phenomenology is extensively documented, Benjamin’s affinity with it has largely gone unnoticed. Accordingly, this thesis provides the first comprehensive account of the phenomenological aspects of Benjamin’s early thought. My central argument is that while both Heidegger and Benjamin employ phenomenological reduction in their early work, they do so from profoundly different metaphysical perspectives. As a result, the sense and trajectory of their phenomenological reductions diverge significantly: Benjamin’s approach remains closely aligned with Husserl’s original intent, whereas Heidegger’s, as Husserl himself rightly observed, does not.