In 2008, the authors published a review that highlighted an emerging trend for medical schools to change their names to those of wealthy donors. Since 2008, the names of ten benefactors have been added to the medical schools receiving their gifts. Twenty-three of the 141 U.S. medical schools accredited by the Liaison Committee on Medical Education are currently named after donors. Large donations have the potential to positively affect all stakeholders by improving the resources that are available for research, teaching, and clinical care, but the rapid increase in the naming of medical schools after wealthy benefactors raises important concerns for those same stakeholders. In this perspective, the authors explore such concerns and identify mitigating strategies that institutions facing these issues in the future can use to ensure that the benefit associated with a gift outweighs any adverse impact. The authors argue for a strong presumption of impropriety when a donor possesses a conflict of interest with the potential to affect clinicians’ judgment. They go on to assess how donors’ control of funds may have an impact on institutional mission and research agenda, and analyze the right of an organization to remove a benefactor’s name for alleged wrongdoing. The perspective considers how renaming may negatively affect brand recognition and the associated impact on students, residents, faculty, and alumni. Finally, it concludes with an analysis of taxpayer-funded organizations and the concern that educational renaming will lead to a slippery slope in which other public goods are effectively purchased by wealthy donors.