The end of the Soviet era and the dissolution of the colossal communist empire have begot significant and radical changes both in the world and in the space soon dubbed “the post-Soviet”. Changes have impacted the post-soviet cities as well especially as regards their image, their trends and policies, their lifestyle and values, etc. – all those transformations occurring in the context of an uncertain atmosphere, marked on one hand, by the Soviet legacy and the recent past sequelae, and on the other, by the seeds of a fragile democracy that was only knocking off in the post-Soviet city in the early 1990s. This article aims at analyzing the metamorphosis of one of the post-Soviet cities - the city of Chisinau - in the period from 1991 to 2011, viewed through the prism of political changes that have been made during the last twenty years of independence. Being a centre and promoter of Moldovan national liberation movement in late 1980s, Chisinau launched - through some of its democracy-minded and pro-European mayors and residents – in a fight for its future – a battle that would result in the abandonment of the “post-Soviet city” label and in the transformation of the city in a truly European capital, where democratic and general human values would rise to the rank of unwritten laws and citizens’ mentality would not accommodate any more nostalgia and/or reminiscent of Soviet times. Twenty years of freedom and independence – accompanied by both feelings of uncertainty and hopes – have demonstrated that achievement of those above-mentioned desiderata is a matter of time, especially due to the fact that from 1991 onwards there have been implemented contradictory policies, appropriate to political colors of all decision makers who have succeeded at the helm of the capital and/or the state. One of such policies has consisted in building and/or re-building monuments in Chisinau glorifying regimes and/or past events, that became – due to different approach to their historical significance – points of rigorous debate in Moldovan society. To those concerns, on one hand, the memorial complex „Eternity” – and on the other hand – on the opposite side of the barricades - the commemorative stone of a monument to the victims of the Soviet occupation and of the totalitarian communist regime. The first one was renovated by Moldovan communist authorities in 2006 and denoted the rehabilitation of the Soviet practices in regard to celebrating the “Victory” day/9 May and/ or the Soviet “liberation” of Moldovan territory. The second one was installed by liberals and the liberal mayor of Chisinau in the Great National Assembly Square, in 2010. The “battle” over monuments, the “battle” over commemorative holidays and dates, the “battle” over mayoralty in June of 2011 – the last being ardently fought between the left-oriented and Europe-oriented citizens – have proved that the process of transition and transformation of the postSoviet city is a demanding and long lasting one. Even though Chisinau has scored notable changes in its evolution over the last two decades - by changing the street names from those with a Soviet flavor to those of national significance; by electing and promoting democratic and open-minded Mayors as it was at least the case of Nicolae Costin; by transforming the Great National Assembly Square in a place of memory; by changing its image and by moving closer towards the European standards - Moldovan capital-city keeps fighting for its future.