This chapter focuses on the need to maximize the education and training of young Italian urban planners in relation to the major challenges connected to the present condition of the country as a place with a strong level of corruption, malfeasance, and Mafia influence. The term criminal informality, by comparing spatial forms and systems of 'regulating competitors', offers some possible strategies for reconstructing the relationship between public institutions and citizens, especially in those contexts such as the illegal urban neighbourhood created by the Mafias as latent planners. The interviews revealed that the average young practicing planner appeared unfamiliar with issues of the illicit powers of criminal organizations and their direct or indirect influences upon urban areas. This was also the case with young planners from the southern regions where organized crime is structurally present and where problems connected to the strong asymmetry of power are both endemic and historically rooted.