The year 2020 is a dividing line in Hong Kong's development as a special administrative region (SAR) under the 'One Country, Two Systems' framework. In response to political disorder and social unrest, seen as a separatist challenge to national authority, the Chinese central government has imposed a national security law on Hong Kong and later revamped the electoral system to ensure that only 'patriots' administer the city. Amid growing local anxieties about the future and international concerns, Beijing and the optimists expect the 'second transition' to get the SAR out of the political conundrum. Pessimists, however, predict the city's demise. It is critical time to consider the prospect of 'One Country, Two Systems' in the new era: Is it being bogged down in a path of retreat or can it open a new page for rebooting the once vibrant and self-confident metropolis?