The poor, women, immigrants, and racial minorities disproportionately bear the social, cultural, economic, and environmental costs of the land-use and natural resource planning processes. These negative social and environmental outcomes can be attributed in part to conventional policy and planning principles, which emphasize competitive, majoritarian, and utilitarian decision-making, but fail to adequately consider moral implications. In response to conventional planning, there are alternative planning theories that emphasize the importance of empowerment, cooperation, and transformation. Through the analysis of two exemplary case studies, the Gila River Indian Community and the Arizona Water Settlement Agreement (AWSA), and the Hawaiian island of Kaho’olawe and the Kaho’olawe Island Reserve Commission (KIRC), the author observes how innovative planning practices play out in real world policy and planning settings. The AWSA and the return of Kaho’olawe are first and foremost stories of activists and community leaders fighting for justice. Federal lawsuits acted as the equalizers that facilitated change and collaborative planning. The uniqueness of the AWSA and Kaho’olawe speak to the serendipitous confluence of historical, cultural and political context. Ultimately, equitable planning practices are the “rational” choice for government officials and agencies.