Aspiration is one of the key factors that have been driving India’s urbanism since independence. The whole idea of defining a new nation on modern cities, which was based on aspirations that swayed towards the skewed image of the developed world still holds true. Such aspirations have more physical manifestations in Indian urban context, as state and central government have more power in cities than the city government itself (even though 20 years have passed after 74th Constitutional Amendment). Delhi presents a special case as land is under the control of the central government and Indian politics at the centre has been for more than a decade now governed by mixed ideologies of the multi party coalition government system. Delhi is India’s power house and urban initiatives that happens here is replicated all across the country, as can be seen from examples ranging from slum eviction to ultra modern metro rail replicated all across the country. Delhi now is on its aspirational image makeover to become a ‘World Class City!’ the new master plan vision, much flaunted by almost everyone in the government and development authorities. Recently Delhi wanted to become like London, before that it was Paris. All these aspirations are mere images which some have enough faith to call a vision, but have no concrete grounding on what needs to be done resulting to urban blunders. Citizens are fed with these images, constantly over different medias by interpreting it differently and as a result there started to have a contestation on urban facets between the authorities and the civil society where by the courts stand as mediators. The contestations have a wide range from mid 90s M C Mehta case that changed the industrial landscape of Delhi, to the ongoing BRT case that questions the very basis of a socialist nation called India.