Despite numerous studies suggesting a path-dependent relationship between transport–land use policies and urban structures, particularly on the emergence of car-oriented development, this connection has rarely been explained with spatial evidence. To address this gap, this paper investigated the historical and spatial urban transformation of Greater Jakarta from three different time periods to understand today’s extensive use of and dependence on private vehicles. This study applied a multi-method approach of (1) historical literature review, (2) computational analysis of the street network using space syntax, and (3) visual analysis of video recordings to allow for a comprehensive insight into the socio-spatial aspects of urbanization as a path-dependent course. The findings indicate that Jakarta’s pedestrian network has been diminishing over time against the well-connected vehicular network. Furthermore, the remaining potential for walking cannot be actualized due to walking inconveniences at the street level. This suggests mobility inequality, since access to citywide urban functions is highly dependent on the access to private vehicles. It also provides spatial evidence that previous policies have had a long-term impact on socio-spatial structures. This paper contributes not only scientific reference for transport and mobility studies in the Southeast Asia region, but also a practical reference for urban planners and policy-makers on how to achieve sustainable development goals and to provide equal access for all.