The late imperial period saw the development of a significant and substantial, although somewhat small, civil society in Kiev. After 100 years, the fall of communism gave way to increasing growth of the public sphere again. Now, however, critics are calling Ukraine’s recent civil society development a façade. What conditions have changed and new challenges arisen in the last century that have affected the function, composition, and capacity of voluntary associations and organizations? Can history shed some light on Ukraine’s current “third sector crisis”? This thesis examines the development of civil society in both late imperial and post-communist Kiev. A historically diverse and foreign-dominated nation, Ukraine has remained a multi-cultural, multi-lingual, and multi-confessional state with large Ukrainian, Russian, Polish, and Jewish populations. In the 19th century, rapid urbanization and industrialization, coupled with declining power of Russian imperial rule, led to a growing public sphere and civil society in urban centers such as Kiev. The increasing number of voluntary associations largely included recreational, professional, and social organizations, which functioned as public spaces for individuals to unite around civic causes. The fall of communism and the collapse of the USSR again allowed for a growing public sphere and civil society in Kiev. The political climate, however, had changed dramatically throughout the 20th century, as had the international system. As voluntary associations increased in number once again, this time much more political in nature, they largely included NGOs, political parties, media groups, and activist organizations, which functioned as information vehicles and mobilizing networks, unifying around nationalist political goals. Kiev’s late imperial civil society developed internally from largely private funding to address social justice issues, whereas Kiev’s post-communist civil society developed with strong elite and external influence, funded by many state actors and international governments, to address political issues and provide financial benefits. The former had substance, but lacked power to influence the state, while the latter had power to change the regime, but lacks substance so much that it has been called a façade. Over the last century, conditions have changed in a way that poses increasing challenges to civil society development in Kiev. This work contributes to the current discourse and understanding of civil society in Ukraine as it has developed historically and in recent years. By placing the case of Kiev in a comparative historical context and a broader regional historical context, it demonstrates how Ukraine’s civil society development follows historical patterns and is inextricably linked to political climate, national sentiment, and international influence. It argues that the nature of voluntary associations and institutions--their function, composition, structure, and societal impact--determines the quality of the civil society. It further suggests mechanisms for change, on several levels, which could serve as the first steps toward improving the relevance, autonomy, and impact of third sector organizations in Kiev.