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This paper examines how negotiations over property rights and land management have long served as tools of autocratic power, with a focus on post-Soviet Ukraine. By tracing the evolution of land management from a century of autocratic governance to the pivotal reforms of the early 1990s, I argue that legacy institutions, most notably the Soviet Ukrainian Land Code, continue to shape contemporary property regimes. The paper analyzes the enactment of Ukraine’s 1991 Land Code and Act “On Property” (Pro vlasnist’), situating it within the broader context of Gorbachev’s Perestroika reforms and Ukraine’s subsequent independence. It reveals a paradox: while post-Soviet Ukraine sought to transition toward Western democratic governance through privatization, the persistence of autocratic legal frameworks and institutional inertia meant that the state retained a disproportionate influence over land and property rights. The paper explores the paradox of Ukraine’s post-Soviet transition. Despite aspirations for a democratic, market-oriented society, the new state, led by figures such as President Leonid Kravchuk, was heavily influenced by Soviet-era institutions and mindsets. The legacy Soviet Land Code served as a blueprint that limited the potential for a radical break from autocratic property management practices. As the government embarked on privatization, the state remained the primary orchestrator of the transition, highlighting the enduring grip of autocratic legal structures even in a nominally democratic context. By highlighting this paradox in Ukraine, the paper contributes to scholarly debates on the persistence of imperial legacies in modern governance, illustrating the complex challenges of transitioning from autocratic systems to democratic governance.