Antiguans and Barbudans have both raised concerns over the disaster recovery solutions put in place to mitigate damages sustained during Hurricane Irma in September 2017. In Barbuda, the potential loss of commonhold land ownership and the possibility of a land grab by foreign investors has tended to portray the island as a victim of disaster capitalism rather than as a resilient community. At the same time, neither island has addressed its vulnerabilities to future extreme events through any substantive legislative response, or immediate policy shifts. While it is vital that we attend to the exploitation of vulnerable populations and the efforts of economic restructuring that follow a disaster to better understand the impact of major weather events, we propose that the threat to commonhold land tenure in Barbuda and the legislative overreach of Antigua’s government on the matter following Hurricane Irma can be understood in terms of various landscape legacies and continuities rooted in ongoing struggles over land in Antigua and Barbuda spanning the periods of slavery, emancipation, and post-colonial independence. This paper situates the past with distinction in order to understand the resilience of land tenure regimes, and the ways in which this resilience affects the quality of post-disaster response in the post-Irma era. Using path dependency theory, we examine the tensions over land tenure in response to Hurricane Irma within the framework of colonial legacies of land rights. More specifically, this paper attempts to examine how these land tenure regimes took shape, and in what ways it has been contested and resisted over time. Our findings demonstrate how the imposition of modern land-use solutions atop a landscape shaped by 18th- and 19th-century practices complicates the mandate to plan for and mitigate the impacts of future disasters. The impact of Hurricane Irma on Barbuda further shows how resistance to legislative change might result in a form of ecological restraint rooted in social-cohesion and commonhold land tenure that is now coming under threat.