The alignment of the above plans with the existing urban planning regulations and the local politics is necessary for securing the viability of such plans, either in the short or the long term. These issues are discussed in this paper. Reference is made in particular to the key elements of the 21st Century Plan for New Orleans. Certain implementation strategies that could enhance the performance of this plan are suggested. At the same time, similar plans related to New Orleans are presented and analyzed at the level that they can be used as the basis for securing the success of the 21st Century Plan.The City Planning Commission has initiated the 21st Century Plan in order to help the gradual recovery of New Orleans. Initially, the above plan seemed to be simple, as of its organizing and execution. In practice, it has been proved as having many implications all of which need to be carefully reviewed so that their effects on the plan are minimized. The key differentiation of the specific plan, compared to others of a similar role, is the following one: the plan has been highly based ‘on the broad participation of the public’ (Neighborhoods Partnership Network 2009, online article). This means that individuals across New Orleans would suggest their ideas in regard to the structure/ content of the Plan. Then, the authorities will take a decision having in mind the following fact: all plans have certain rates of failure, other more and other less. Also, amendments would be allowed, since the needs of people and the technological advancements can be differentiated through the decades. This means that the flexibility of the Plan would be a key requirement, among other characteristics, for its success.