Hahnemann University Hospital provided care for Philadelphians starting in 1848, but its recent history has been riddled with financial turmoil that culminated in its rapid closure in summer 2019. As the hospital shuttered its doors to patients, it also orphaned 583 medical trainees. This crisis exposed vulnerabilities in graduate medical education (GME). In a firsthand account of the situation that developed in Philadelphia and reached academic institutions across the country, the authors reflect on lessons learned that may help leaders at other institutions mitigate the inevitable difficulties that arise when academic hospitals close. These lessons pertain to handling panic and administrative burdens in the aftermath of closure, the importance of well-defined processes, a clear understanding of GME funding, and strategies for placement of trainees that minimize disruption of their education.