This paper investigates the structure of interplay in cross-scale linkages between stakeholders in resource management. Cross-scale interactions emerge because of the benefits of individual stakeholder groups in undertaking them. Hence there are uneven gains from cross-scale interactions. The political economy framework outlined in the paper suggests that inequality in power-weighted decision-making has consequences for winning and losing groups within cross-scale interactions. Cross-scale interactions by powerful stakeholders have the potential to undermine trust in resource management arrangements. If government regulators, for example, mobilise information and resources from cross-level interactions to reinforce their authority, this often disempowers other stakeholders such as resource users. Offsetting such impacts, some cross-scale interactions can be empowering for local level user groups in creating social and political capital. These issues are illustrated with observations on a fragile co-management system for resource management in a marine protected area in Tobago in the Caribbean. The case study illustrates that the structure of the cross-scale interplay in terms of relative winners and losers, determines its sustainability.