Daniel Bensaïd (1946–2010) was a leading figure of May ’68, a Marxist thinker and an influential French public intellectual. His theoretical and political trajectory is divided into two distinct periods separated by the historical turn of 1989: the fall of the Berlin Wall and the end of the ussr. This also coincided with an existential turn due to his contracting aids, which brought him close to death. After this turn, he played the role of a ‘border-crosser’ between generations, intellectual currents and geopolitical areas within the radical left. In the 1990s, he began a critical rereading of Marx and tried to transcend Trotskyism, confronting its legacy with other currents of critical thought, notably the Frankfurt School. Since this pivotal moment, his writings reveal a permanent and intense dialogue with the work of Walter Benjamin, which he reinterpreted in a contemporary, political perspective, rethinking the political dilemmas of the twenty-first century through a Messianic vision of history. This article emphasises the affinities between two historical constellations – 1939 and 1989 – which, in spite of their obvious differences, were equally shaped by a feeling of defeat, and allowed a fruitful ‘encounter’ between French and German philosophers.