Modern concerns that medical students and trainees suffer a loss of empathy during medical training have generated handwringing, research, and innovation. But a literary vignette from a well-known American author reveals adverse attitude changes during medical training have been noted for more than a hundred years. Loss of empathy and rise of cynicism among students has been a subject of academic scrutiny for many decades though the focus has shifted from deficiencies of the student to deficiencies of the care delivery system in which they learn. The causes of empathy loss were recognized in the vignette and are little changed: exhaustion due to the stress and burden of working with the acutely ill in high volume, a devaluing of patient suffering due to insecurity about one's own clinical competence, and working within health care systems that do not celebrate empathy or its sister virtue compassion, as useful or desirable skills on the road to clinical competence. But data is available that links empathetic relationships with many types of improved clinical outcomes. Evidence-based tools for relationship building are available for adaptation in the student/trainee situation. Educators should emphasize the link between empathy and improved clinical outcomes in designing empathy-sustaining curricula.