The influence that Hölderlin’s work had on the young Benjamin has been widely studied and debated. Little or nothing has been said, however, about the importance that Hölderlinian works and concepts had in Benjamin’s later thought. For much of the critical and biographical literature, it is as if Benjamin’s dense ruminations ended abruptly after 1924, as Benjamin completed his work on the Origin of German Tragic Drama and engaged in a complex relationship with Marxist thought. However, the contention that such a rupture actually occurred in Benjamin’s work is theoretically unconvincing. The aim of this paper is to unearth Hölderlin’s contribution to the articulation of the ethical perspective that drives Benjamin’s later reflexions on aesthetics and politics. Two sets of issues are addressed here: the identification of Hölderlin as the “bone of contention” between Benjamin and George’s circle and the identification of Hölderlin as an important link connecting Brecht and Benjamin.