Indiana University-Purdue University Indianapolis (IUPUI) / The collapse of communism and the fall of the Soviet Union offered an unprecedented opportunity for the international community to support transitions to democracy in a region that had long known only totalitarian rule. Among the key players engaged in supporting efforts were U.S. grantmaking institutions, including both non-state and quasi-state aid providers. This thesis explores the motivations and evolving strategies of three different types of grantmaking institutions in a single country, Russia, with a particular focus on democracy aid provision from 1988-2002. The three types of grantmaking organizations examined through case studies include: the Ford Foundation, a private foundation with a history of international grantmaking spanning several decades; the Charles Stewart Mott Foundation, a private foundation known primarily for its domestic focus with a much shorter history of international grantmaking; and, finally, the National Endowment for Democracy, a U.S. government-created and heavily taxpayer-funded organization established as a private nonprofit organization to make grants specifically for democracy promotion. Motivating factors for initiating or expanding grantmaking in Russia in the late 1980s included a previous history of grantmaking in the region, a previously established institutional commitment to democracy promotion, international peace and security concerns, and interest from a top institutional leader. Over the course of the fourteen year period studied, five grantmaking features are identified as influencing the development of grantmaking strategies: professional grantmaking staff; organizational habit; global political, social, and economic environments; market and other funding source influences; and physical presence. Though subject to constraints, the non-state and quasi-state grantmaking institutions included in this study were able to avoid weaknesses identified with private philanthropy in other research and demonstrated a willingness to experiment and take risks, an ability to operate at the non-governmental level, and a commitment to long-term grantmaking, informed by expertise.