Background: Residents with performance problems create substantial burden on programs and institutions. Understanding the nature and quality of performance problems can help in learning to address performance problems. Aim: We sought to illuminate the effects of resident performance problems and the potential solutions for those problems from the perspectives of people with various roles in health care. Methods: We created a composite portrait from several residents who demonstrated a cluster of common performance characteristics and whose chronic or serious maladaptive behavior and response to situations created problems for themselves, for their clinical colleagues, and for faculty of their residency program. The composite was derived from in-depth interviews of program directors and review of resident records. We solicited practitioners from multiple fields to respond to the portrait by answering a series of questions about severity, prognosis, and how and whether one could reliably remediate a person with these performance characteristics. We present their perspectives in a manner borrowed from the New England Journal of Medicine's "Case Records of the Massachusetts General Hospital." Results: We created a composite portrait of a resident whose behavior suggested he felt entitled to benefits his peers were not entitled to. Experts reflecting on his behavior varied in their opinion about the effect the resident would have on the health care system. They suggested approaches to remediation that required substantial time and effort from the faculty. Conclusion: Programs must balance the needs of individual residents to adjust their behaviors with the needs of the health care system and other people within it.