Within the special issue, this paper aims to contribute to the debate on VIP urbanism in specific relation to phenomena of alpha territorialisation. Accordingly, it tries to apply this international figure to long-term analyses of the Milan case study, which can be considered an original intersection between the articulation of urbanisation and socio-spatial polarisation processes in the Italian national context and the dynamics of global cities, integrating international trends with site-specific characteristics. On this background and in relation to a comparison with the London case study, the article retraces the recent evolution of spatial processes, policy and planning in the Milan urban core: on the one hand, by recognising different local strategies, phases and possible meanings of phenomena of alpha territorialisation; on the other hand, by identifying open challenges for further research, policy making and planning. Two issues seem worth to be underlined and further explored: both the characteristics and spatial effects of super-rich in Milan, and the opportunities for value-capture mechanisms to work.