This paper will discuss the paradox of Jakarta that embedded in the process of urbanization process of the city, since the colonial periods until the last decade of the twenty-first century. The discussion of the paper will depart from the notion that the urban dynamic of Jakarta is seen as the co-product of local cultural power with the social process that happening in the wider arena, i.e., capitalism. In this regard, the capital city of Jakarta has been massively integrated into the scaffolding of the world economy since Indonesia open the liberalization window in 1971. The significant number of the capital influx energizes the urban development in Jakarta and all the cities in the country including the nearby cities of the major city Jakarta. At this point, the rapid urbanization process has been taking place in socio-cultural context of Indonesia that be motorized mainly by the state, the business, and the society including the kampong dwellers. In this connection, urban characteristic of Jakarta has been marked by the presence a comparatively wide disparities among the well-to-do and the poor people. In this connection, the issue of bridging the urban paradox of Jakarta with a holistic approach is highly important. Learning from the past failure, the urban justice approach and agendas of the city must be transformed into more comprehensive, humanistic, and democratic form. In this regard, it is matter to introduce policy that the poor has an access to the land rights as well urban political agendas. However, it is also urgent to empower the poor as the potential and equal actor to the urban development, with pertaining historical backgrounds, socio-economic aspects, political concerns, gender issues, sustainable dimensions, as well the culture, especially local wisdom.