Recent decades highlight an extraordinary growth of casino gambling all over the world. In the race to build casino-cities, particularly to reap economic and social benefits, most aspirers look to replicate the development models of the most famous casino-cities known to date, Las Vegas and Macao. Countries that have modelled after the aforementioned casino-cities have had mix results of success; e.g., Singapore, which followed Macao, yielded considerable success, while other states of the US which modelled Las Vegas, such as Atlantic City, did not have as much luck. In this respect, the countries adhere to the words of the wise; “Standing on the shoulders of the giants”. Yet, perhaps explaining why no country can really replicate the successful development experiences of Las Vegas and Macao, most countries fail to see beyond the glitz and glamor to recognize the key challenges and opportunities that helped make Las Vegas and Macao; e.g., with respect to the presence of domestic organized crime groups. This paper delves deep into identifying the key actors and circumstances that made the aforementioned cities what they are today, elucidating the integral development strategies used during their formative years. Utilizing a Marxian approach to understanding the state and state-civil society relations, the paper elucidates why no country can really replicate the development models of Las Vegas and Macao without appreciating its socio-political characteristics and the intricate ties between the upperworld and underworld during their formative years. In light of the findings, recommendations are provided for future research and pragmatic endeavours.