In Berlin, throughout the last 30 years, sales of state-owned property to reduce the city’s debt were defended as a land policy without alternative by policymakers. These solutions in land policy were not discussed as an ethical issue but as pragmatic considerations. This article reframes Berlin’s land policy as a wicked problem, an approach justified and critically outlined by multiple risk perceptions and ethics in planning. Ethics in planning and myths of property relations are derived from Cultural Theory (CT). Following this typology, risk perceptions and preferred tendering processes in Berlin’s land and real estate policy between 1990 and 2020 will be analysed as monorational re-solutions. Building on a literature and policy review, as well as 20 expert interviews, this article examines today’s expectations towards land policy and identifies five periods of monorational re-solutions and their waves of intergenerational consequences for present and future generations. To illustrate intergenerational injustice in land policy, according to CT, the article puts forward a typology of risk perceptions in tendering processes.