In the past two decades, two big processes have changed the urban configuration of Jerusalem: The construction of the West Bank separation barrier, leaving the majority of the Palestinian neighborhoods of the city completely cut out from their hinterland and neighboring Palestinian cities, and the ongoing planning and construction of the light rail project in Jerusalem. The light rail project is a part of a transportation infrastructure upgrade that came as a response to the city’s urban sprawl and its heavy traffic problem. These two processes seem to be of a contradictive nature: one is of absolute separation and segregation, and the other is of interconnection and integration. The truth, as always, is more complex, and these two processes are deeply rooted in the colonization of the city. This thesis researches the relations between urban planning and the process of colonization, and, in particular, the role of transportation infrastructure in manifesting colonization patterns in the urban space in the city of Jerusalem. It analyzes the dynamics that influence urban planning in a divided city that is subjected to urban conflict and examines the problems, urban damage, and social injustice that are caused by it. The design part of this thesis explores the potential of urban planning and design as a means of a decolonization and reconciliation process and proposes a transition to a transit-oriented development framework to support it. From the understanding of the powerful role that transportation infrastructure plays in the colonization and segregation of the city, the main research question of this thesis is: How could Transit-Oriented Development (TOD) serve as an instrument for decolonization and inclusion in Jerusalem? To answer this question, this thesis takes the approach of alternative planning – grounded on the existing spatial and social conditions of the city while exploring alternative urban planning and design given a different political framework. This approach enables a critical debate about existing narratives and assumptions, stimulates discussion, and imagines a different future beyond existing political constraints. The design part of the thesis consists of three levels: Strategic planning, in the form of a city-scale urban vision that explores a transit-oriented development framework to the city as a means for decolonization. Governance design, exploring implementation strategies and governance transformation to support the urban vision and implement it on the local scale. Urban design: Two key projects on a local scale are designed in important nodes of the urban vision. The design of the key projects examines the implications of the urban vision on the local scale and explores the potentials of decolonization on the urban form and public space.