Island systems have limited geographical, ecological, and social capacity to metabolize waste materials produced by the economic activities of their growing populations. Conceptualized as a ‘wicked problem’, the faults and weaknesses in waste management systems on islands continue to cause acute and cumulative ecological and human health impacts. Trinidad and Tobago is one such island jurisdiction grappling with this situation, particularly being a petroleum-dependent economy. Through the lens of neo-institutional theory, this case study of waste management in Trinidad and Tobago unpacks the efforts, reactions, drivers and circumstances that have led to various successes and failures but no definitive solutions over time, especially regarding plastics and packaging materials. We identify three temporal phases of policy evolution that have altered the waste metabolism trajectory to date: (1) government led patriarchal approach of traditional landfilling combined with behavioral change campaigns to reduce, reuse, and recycle, (2) to a more democratic, shared burden, public-private partnership approach combined with attempts at incentive-based regulations, (3) to the present, more private sector-led voluntary bans on production and use of plastics. This study contributes to our understanding of the institutional factors that shape the search for solutions to the wicked problem of island waste metabolism.