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The fall of Soviet Union in 1991 symbolised the victory of democracy over communism. In the rush to consolidate democratic forces, the president Boris Yeltsin initiated several reforms in governance and economy. But the common man of Russia was far from enjoying the fruits of democracy. Yeltsin''s privatisation agenda of the 1990s, though acclaimed to be a success at that time, later posed serious hurdles to modern Russia. One of the offshoots of the privatisation programme was the emergence of Oligarchs, whose proximity to the Kremlin won them covert political favours and business deals. When Vladimir Putin came to power in 2000, the nexus of politics and Oligarchs started falling out. Though Putin partially succeeded in keeping a tab on Oligarchs'' political activities, he could not sufficiently convince the world about the Kremlin''s integrity. This has cost Russia dear in terms of foreign investment and international diplomacy. This case study attempts to tie all the loose ends that led to the persecution and the eventual exile of Oligarchs. The case study also delves into the process of the infamous privatisation of the 1990s, which many observed as the root cause for Russia''s present-day problems.