Managed retreat (MR) involves permanent resettlement of existing households and communities away from areas at risk, here coastal flood risk. On post-Sandy Staten Island, New York, where MR has been successful, our research findings from interviews and a focus group of key stakeholders and commentators indicate there are very significant political impediments as well as financial constraints to MR programs being successful without the experience of a disaster and a repetitive sequence of hazardous events. Pre-disaster and long-term plans for reducing risks in such vulnerable areas are easy to advocate but not to implement. Many coastal locations globally will need some form of MR, where current risk is very high as a legacy of past decisions and where many communities will not be defendable against the expected future sea level rise. With leadership and community commitment locally MR agendas can and should be pursued: the optimistic scenario. But success appears likely only in the aftermath of a major disaster. This suggests strongly that we may have to await those inevitable disasters, and then be ready to act, rather than vice versa: a worrying conclusion and a dismal prognosis.