The article deals with the status of constitutional and legal support for the realization of the status of the city of Kyiv as the capital of Ukraine, as well as the conceptual problems of the current legislative initiatives in the sphere of local self-government and executive power in the city of Kyiv, using the experience of expert analysis. It is noted that over the years that have passed since the adoption of the legislative acts that determined the peculiarities and specifics of the organization and functioning of local self-government and executive power in the city of Kyiv, the corresponding relations have developed quite contradictory both in terms of the implementation of capital functions and activities of organizational structures of the city authorities, first of all, the Kyiv mayor, the Kyiv city council, the Kyiv city state administration, implementation of management in the districts of cities, etc. The set of objective and subjective reasons, legal, political and socioeconomic, internal and external factors, which necessitate improvement of legislative support of the organization and functioning of local selfgovernment and executive power in the city of Kyiv, are considered. A critical analysis of the drafts of the new version of the Law of Ukraine «On the Capital of Ukraine – Hero City Kyiv» is carried out (Reg. No. 2143 of 13.09.2019; Reg. No. 2143-1 of 19.09.2019; Reg. No. 2143-2 of 24.09.2019; Reg. No. 2143-3 of 24/09/2019). It is proved that these draft laws contain a number of conceptual shortcomings related to the regulation of metropolitan functions, the status of local self-government and executive power in the city of Kyiv, their tasks and competences, the place and role of the Charter of the territorial community of the city of Kyiv in the process of solving urban issues values, etc. The general conclusion is that the mechanism of implementation of local self-government and executive power in the city of Kyiv is extremely contradictory and inefficient, and modern legislative initiatives in the sphere of ensuring the status of the city of Kyiv not only eliminate the existing gaps and defects, but also create new problems of political, legal and socioeconomic, functional and institutional nature.