Despite not being the first mass protests that claim Hong Kong's autonomy since the handover from British rule back to China in 1997, the 2019 protests has taken a historical character. However, the future remains uncertain. The protestor’s claims that started by asking to meet some commitments are now about claim for democracy transition as the only way out. The political crisis in Hong Kong has affected the fragile relationship with China and also confirms that the "one country, two systems" principle is in deep crisis with potential repercussions in Taiwan. This paper presents an analysis of the political crisis and its impact on the region through the historical and political context of Hong Kong, Beijing and Taiwan.