Hong Kong used to be a major gateway to China and an intermediary between China and the world particularly the West. However, the world has changed now. Intense US-China rivalry, regional conflicts and anti-globalisation sentiments are defining the new normal. Also, China has transited from an era of reforms through opening to Western markets and methods to the present new era of the China path to modernization. After 2019 China has taken national security as a priority in the city while the doubtful West now sees it as a system less separate from the mainland. Hong Kong seems caught in a dilemma and risks losing its strategic distinctness and connectedness. Can it reinvent its intermediary role in a more complex and polarized world?