This article examines the political, socio-economic, and military foundations of Ukraine’s first modern bid for statehood during the years 19a14–1921, focusing particularly on the role of Symon Petliura and the Ukrainian People’s Republic (UNR). It argues that Ukraine’s drive toward independence emerged not from an early separatist consensus but from the radicalization of the Russian Revolution, the collapse of imperial authority, and the Bolshevik coup of October 1917, which constituted a decisive breach of loyalty between Ukraine and the disintegrating Russian Empire. The analysis highlights three key dimensions of the Ukrainian revolutionary project: the evolution of political programs from autonomy to sovereignty; the centrality and unresolved nature of the agrarian question; and the attempted nationalization (Ukrainization) of the armed forces as a substitute for absent state structures. Particular attention is paid to the political thought and actions of Petliura, Vynnychenko, and Hrushevsky, whose differing ideological commitments shaped both the possibilities and limitations of the Ukrainian struggle for self-determination. While external powers viewed an independent Ukraine as incompatible with their strategic interests, and internal divisions undermined the consolidation of state institutions, the revolutionary experience forged a durable idea of Ukrainian statehood. The article concludes that although the UNR ultimately failed, its legacy – especially the political agency embodied by Petliura – created a foundational narrative that resurfaced in 1991 with the successful realization of Ukrainian independence.