Nonprofit healthcare organizations are confronting an unprecedented series of challenges as they strive to maintain positive operating margins in the face of declining reimbursement from insurance companies and governmental payers. The crisis is particularly acute at smaller and mid-sized organizations. Having played a major role in their communities for decades, they are finding that the healthcare business model is changing. Medical practice models are being upended as many doctors are closing their independent clinical practices and becoming hospital employees in response to decreasing reimbursement levels and ever-greater demands for capital investment, and in pursuit of a more manageable professional lifestyle. In hospitals and clinics, the old-style model of brick-and-mortar buildings located in major urban centers is being challenged by new delivery systems such as suburban mall-style "big box" shell structures with flexible wards that can easily be changed in response to the advent of new equipment and practices, free from the strictures of plaster walls and concrete slabs. This paper will argue that healthcare organizations must consider adopting the endowment management model that has been developed over the last three decades by educational institutions and increasingly copied by other types of nonprofits. The fact that it will take healthcare organizations several years to implement these changes and begin to reap their benefits makes this task all the more urgent. Along the way, leaders of healthcare organizations will need to consider the following questions: What is the role of the endowment in our healthcare organization? How do actual and potential donors evaluate our skill in managing our present endowment? How can we make the case for larger endowments--and contributions--at a time of fiscal uncertainty? It is in the interest of healthcare organizations, rating agencies, and donors that healthcare endowments evolve toward becoming more like those of other long-term nonprofit institutions.