The choice of analysing the Olympic Games of Rome 1960 and Barcelona 1992 belongs to the conflicting and diverse impact generated on the two cities. These two events created a big urban transformation, which allows for a new critical perspective concerning public services and management measures. I will examine how management models either prevent or increase the exploitation of the intangible benefits, necessarily associated with the Olympic event. Olympic venues are at the heart of Olympic planning, as they constitute the citizens’ Olympic legacy. In fact, these venues’ sitting capacity and their technology determine their future use and value among the citizens, possibly enhancing the sportive practice within the local community. The Olympic venues` design, supported by a strong public transportation system, is therefore of pivotal importance in order to develop a new and stable city economically able to apply its own resources and to limit the environmental impact, like cost instability. My critical analysis regarding these two mega-events is carried out through the development of 13 guidelines, aiming to offer effective criteria in order to guarantee not only an economic revenue but also intangible, future benefits. This investigation shows how cities should gain from these intangible benefits, which develop as a consequence of both the Olympic bid’s success and the infrastructural evolution. Only thanks to these new philosophies, cities and regions, as a consequence, could profit from the intangible benefits belonging to the Olympic Games, including employment, structure and infrastructure use, tourism, job offers, SME, cultural development, decision making, and trade.