This article responds to the relative neglect of reading Mahmoud Darwish from a postmodern perspective. Inspired by postmodern theory, we suggest that Darwish after the Oslo agreements in 1993 has a displaced and dialectical relationship with the collective identity; he utilizes a transition from being into becoming, from filiation into affiliation, knowingthat this transition mirrors rifts, ruptures and fractures in the Palestinian historical and geopolitical conditions in the post-Oslo era. By looking at poems written after the Oslo Accords, which were described by Bashir Abu-Mannehas ‘the root cause of the disintegration and liquidation of Palestinian agency’, we argue that Darwish’s persona manifests the postmodern intellectual who is tempted to leave the collective and expatriate himself to hone an independent self and thought that provides a fresh perspective and a new understanding of Palestinian collectivity (2016, 159). While Darwish’s pre-Oslo poetryexpressed a collective voice, identification and commitment to the national narrative, he, after Oslo, becomes more personal and, perhaps, detached from and critical of nationalist political entities and narratives. Building on theoretical insights from both postcolonial and postmodern intellectuals, we also articulate ways in which the dialectical relationship between postcolonialism and postmodernism appears in Darwish’s poetry. We find that the persona at times combines, and at other times, fluctuates between singularity and multiplicity, certainty and suspicion, the collective and the personal, place and space, tradition and innovation while seeking revision, transition, contingency, dynamism, and fluidity which are especially needed at this post-Oslo period.