Portraits of clinicians quickly became emblematic of what the COVID-19 pandemic has demanded of everyone, especially caregivers who witnessed deaths likely unprecedented in number during their careers. This article describes an arts-based research protocol exploring portraiture as a medium for representing and understanding clinicians’ experiences, mostly during the first year of the pandemic. This article presents Shadow of Corona, a large oil on canvas portrait commissioned by the AMA Journal of Ethics to commemorate the American Medical Association’s 175th year. The article also includes Sarah, a charcoal study drawing for that portrait, and Front Lines of Care, a 3 by 3 collection of 9 smaller oil on canvas portraits