In 1999, the City of Los Angeles passed the Adaptive Re-use Ordinance (ARO). Eighteen years later, Downtown Los Angeles is attracting more and more residents and has become the main center of the city’s new transportation network. Using adaptive re-use as a driver for urban regeneration, developers have transformed the former disaffected downtown into a desirable place to live. This chapter identifies that the planning innovation is the result of negotiations between different stakeholders groups. However, social sustainability could be enhanced by introducing policies to maintain a certain percentage of affordable housing in re-use projects. The entrepreneurial nature of adaptive re-use strategies in the LA context has prioritized economic revitalization over social considerations.