Drawing on a comparative case focused on two communities stationed at entrances to the Great Smoky Mountains National Park, the most visited national park in the US, we empirically test and extend theory on civic wealth creation (CWC), which involves the collaboration of multiple independent stakeholder groups to generate not only economic but also social and communal benefits for communities. Specifically, we trace the historical development of Gatlinburg, perhaps the most famous gateway community in the US, as compared to its unsung neighbor to better understand how interactions between the three independent stakeholder groups considered in CWC (enterprises, regimes of support, and community members), produce such stark differences in development over time, and with what effect on the types and amount of wealth created. We find that the alignment of stakeholder goals and the distribution of power across stakeholders accounts for differences in how civic wealth is created, sustained, or diminished over time. As such, this study offers an empirical advancement of civic wealth creation by identifying important mechanisms that drive the creation of different types of wealth for communities. In doing so, we examine how diverse stakeholders leverage purpose, policy, and entrepreneurship to create and distribute value for communities.