This empirical and interdisciplinary study investigates the contribution of deeply enrooted social-political factors to the accumulation of exposure and vulnerability and amplification of cascading impacts of disasters, with implications on the creation and reinforcement of path dependency maintaining social-ecological systems on a maladaptive trajectory. Applying the Trajectory of Exposure and Vulnerability approach to Saint-Martin (Caribbean), we more specifically highlight how the causal chain linking historical geopolitical and political-institutional drivers to legal, economic, demographic, sociocultural, planning-related and environmental drivers, created the accumulation of exposure and vulnerability over time and contributed to the propagation and amplification of the impacts of tropical cyclones Irma and José in 2017. We find that historical social-political dynamics involving unsustainable development and settlement patterns, the weakness of local institutions, population mistrust in public authorities, high social inequalities and environmental degradation maintained Saint-Martin on a maladaptive trajectory through powerful reinforcing mechanisms operating both between and during cyclonic events. This study demonstrates that long-term interdisciplinary approaches are required for a better understanding of path dependency and the identification of levers to break it in risk-prone contexts. In Saint-Martin, breaking path dependency requires the alignment of local institutional capacities with national risk reduction policies, the promotion of social justice and involvement of local communities in decision making. This study therefore confirms the relevance of backward-looking approaches to support forward-looking climate adaptation.