Worldwide human population expansion and rising standards of living place increasing pressure on wildlife populations and their habitats. Conflict regarding conservation and preservation of endangered species is among the greatest challenges of the 21st century. Endangered species management on private lands magnifies the problems encountered by natural resource policy-makers and managers. Given that conservation of endangered species increasingly depends on securing cooperation of private property owners in local communities, understanding how to secure that cooperation is important. We used an ethnographic approach to critically review the Habitat Conservation Plan (HCP) processes used in attempts to develop regional HCPs to benefit the Houston toad (Bufo houstonensis) and the Florida Key deer (Odocoileus virginianus clavium; hereafter, Key deer). In both cases, the process was framed as a search for the optimum solution through collaboration and consensus building, and in neither case was the solution achieved. The paradoxical nature of liberal democracy precluded the possibility of a single, ideal solution. Failing to find the optimal solution led to disillusionment and pessimism with the process among HCP participants. We suggest that within democratic political contexts, approaches to conservation planning that center around bounded conflict, which is rooted in acknowledgment of the paradox inherent to the ideals of liberty and equality, are more likely to produce satisfactory results than are consensus-based approaches.