This paper expands the repertoire of comparative urbanism by putting forward a method of ‘hopeful comparison’, in which we explore an asynchronous comparison between post-war Poland and Syria. Similar to the way that Polish architects used urban design as a ‘practice of hope’ during the Second World War, contemporary Syrian architects are now drafting reconstruction plans even if their implementation does not seem politically possible. Yet what role can an ethical, affective stance such as hope play in the methodology of comparative urbanism? In our comparative strategy the role of radical hope is threefold. First, it creates the comparative connection between two cities destroyed by urbicide, thus countering the destructive connectivities of war and, in case of Syria, capitalism, and foregrounding resilience and human connection (which also opens up the potential of healing). Second, radical hope provides a temporal reorientation of knowledge, redirecting the analysis from the traumatic past towards an open future. Third, in this way a hopeful comparison becomes a practical tool for thinking through concrete ethical and political dilemmas concerning reconstruction and property regimes. How to think about reconstruction when the conflict is still ongoing, and, if the property system is now weaponised as part of the conflict, how to avoid inadvertently reproducing this violence in the process of property restitution and reconstruction.