Russian transition has not been a revolutionary jump from the totalitarian order to an ideal market economy and democracy but an incremental process that has so far resulted in a hybrid system aptly called “oligarchic capitalism”.  We study the evolution of the first post-communist oligarchy through examining the careers of 296 most prominent first-wave post-communist business tycoons.  We find that 43 percent of them consisted of “insider oligarchs” deriving their status from privileged nomenklatura background dating back to the previous regime.  The rest were "outsider oligarchs" who did not have such background.  Compared to insider oligarchs, the outsider oligarchs were younger, had higher-quality human capital and were disproportionately Jewish.  Their first major business success tended to happen in sectors neglected in the planned economy.  But the overwhelming majority of them subsequently developed their own special relationship with the government.  It appears that instead of changing the rules of the social-economic game, the new entrants were themselves changed by those rules.