Hong Kong was described as a “city of protests”, long before the 2019 Protests, by its Special Administrative Region Government, in dialogues with international interlocutors, in part to promote a positive image of difference from Mainland China and in part to address criticisms against its public order legislation. That is now very much a matter of the past. This paper considers the watershed years of 2019 and 2020 when expressions of dissent in Hong Kong since resumption of exercise of Chinese sovereignty in 1997 have morphed from peaceful, symbolic and occasional to violent, divisive and sustained. Two lines of discussion follow. The first reflects on the so-called “#bewater” approach of dissent/resistance that seemed formless, multiplicated and apparently leaderless at the time. The second considers the errors on the part of the protesters and the regime responses that have now resulted in the incarceration, exile, disqualification, disenfranchisement and silence of many.