Most studies in the ‘world cities’ literature tend to frame the global connectivity of cities in the context of a specific form of globalization that began unfolding in the 1970s (i.e. the ‘new international division of labor’). In this paper, we argue for the need to frame the global connectivity of cities in long-term urban trajectories across different phases of globalization. To this end, we explore the trajectory of the Jakarta metropolitan area (JMA) from the period prior to the arrival of Western merchants into Southeast Asia into its current role as being one of the major cities in the Global South. We find that the emergence and ensuing path-dependent evolution of the JMA into a strategic site of economic globalization is linked with its initial formation as the Dutch strategic base for securing and expanding its commercial system in Asia and the repeated explicit and implicit privileging of the city as a strategic site for engagements with the wider global and regional context by the national government. The character and function of the JMA in the current stage of global economy is, therefore, a product of a long-term evolutionary process with different phases co-producing Jakarta into what it has become today.