In recent decades, physicians have diagnosed fictional and non-fictional characters through portraits, biographies and writing. We argue that such an exercise can be beneficial for a uniquely health humanities reason—better understanding of our current world and the social determinants of health. Drawing on the method of health and social justice studies, we explore the character of Shosha, who appears repeatedly in the writings of Nobel Prize winner Isaac Bashevis Singer. Singer’s strong story-telling skill and commitment to writing about the Jewish communities of prewar Poland in vivid detail preserve a slice of history, ensure that future generations will better understand what was destroyed by Nazi extermination policies, and provide lessons for modern political, hunger and war threats to human health. Shosha suffers from a lifelong debilitating disease that neither Singer nor subsequent commentaries ever name. The authors focus first on diagnosing the disease by consulting medical literature and experts. They then examine the value and pitfalls of this exercise and suggest that the lessons of understanding the disease historically, for teaching physicians how to recognise diseases rooted in war and poverty, and for enlightening all of us to the risks faced in human health by a world increasingly taking up arms and sliding towards fascism make diagnosing Shosha necessary and meaningful.