During Russia’s Imperial and Soviet past and following the end of the Cold War, Western observers have associated Russia’s foreign policy with expansionism in the near abroad, and, in turn, this has been met by a policy of containment in the West, with some resulting in international conflict. In that regard, the behaviour of the post-Yeltsin Russian government has drawn a similar response by contemporary analysts. In light of the ongoing debate about Kremlin’s motives, this paper seeks to analyse the nature of the Russian ‘threat’ towards its neighbours by examining the relations between Ukraine and Russia since 1991 from the viewpoint of the Ukrainians. Relations between Ukraine and Russia have been viewed as a critical component of Russia’s near abroad policy. Due to historical, linguistic, and cultural links, Russians view Ukraine as their cultural birthplace and an inseparable part of Russian national identity. There is some official support by the Russian government for this position. Thus, attempts by Ukrainian authorities to establish greater sovereignty and independence from Moscow have been frequently met with Russian opposition in cultural, diplomatic, trade and security spheres. The key question emerges: what role has Russia played and how in Ukraine’s foreign policy? Through the in-depth examination of four case studies – Ukraine’s denuclearization in the early 1990s, the division of the Black Sea Fleet of 1997, the reversal of Odessa-Brody pipeline in 2004, and the Russo-Ukrainian gas crisis 2009 – I was able to construct four foreign policy making systems of Ukraine, which were in transformation since 1991. This systemic analysis reveals not only how Moscow was able to influence Ukrainian politics to benefit Russian interests, but under what domestic and external conditions it was able to do so.