Between October 2019 and March 2020 Chile experienced the most massive and heavily repressed cycle of social protests in its post-dictatorship (1973–90) history. This essay explores the social uprising as a critical event of political subjectivation through the story of Ricardo, an ordinary young medical technician with no background of political affiliation who fully immersed himself in the forefront of confrontation with the police in the ground zero protest zone, while also providing first-aid assistance to those injured. Two vectors triggering Ricardo’s unexpected and sudden transformation into an activist are identified: the intergenerational potency of antidictatorial memories and the power of the spontaneous multitude in demonstration. In recalling the dictatorship, Ricardo and his friends used to ask themselves, “What would I have done if I’d been there?” In the face of the social uprising, Ricardo brings to the present that generation-specific question and responds with total exposure, defending the multitude and healing the wounded. We argue that the event’s critical nature is interpreted in the light of the past. Ricardo’s involvement becomes an ethical imperative to his time and to his own history. This duty fuels his mobilization and desire for social transformation, blurring the analytical boundaries between ethics and politics.