This study focused on the allocation decisions that college and university leaders make with potentially transformational donations and their associated decision-making processes. A gift was defined as potentially transformational if it was: 1) unrestricted and 2) exceeded 25% of an organization's annual revenues or existing endowment. These types of donations are extremely rare, and the use of such gifts is an understudied element of strategic financial decision-making in higher education. Qualitative case study analysis of eleven institutions that received potentially transformational donations from MacKenzie Scott in 2020 or 2021 was employed to explore how higher education leaders utilize gifts like these and the extent to which organizational characteristics and contexts influence the associated decision-making processes and choices. Case study sites were selected using stratified purposeful sampling to include a variety of allocation decisions and decision-making processes in the study. This study found that the professional backgrounds, leadership styles, and strategic preferences of college and university presidents had an outsized impact on the use of potentially transformational donations and the associated decision-making processes. Presidents influenced the allocation process by using framing to guide the development of choice sets for subsequent consideration. In addition, entity-specific characteristics and contexts also provided vital inputs into each college's calculus regarding what to do with the potentially transformational donation. These characteristics and contexts include locational factors, financial factors, and other entity-specific considerations. Inferred donor intent provided a third input to the allocation process. In the absence of donor restrictions, recipient organizations made sure to use the donations in a manner they believed the donor would approve. Outcomes ranged from highly conservative allocations, to bold choices to invest Scott's funding in experimental programs and capital expenditures designed to drive flywheels of financial and other returns. The study also found that adequately characterizing the decisions explored in this research required nuance, and the presence of related foundations may prompt additional considerations. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]