Democratization didn't work cause the economy was primed for oligarchy after the fall of the soviet union, the economy was liberalized so quickly that democracy couldn't follow. The dream was never democracy in Russia, it was to completely privatize the oil and gas industry for foreign investors, surprise surprise, russian oligarchs take over and seize power for themselves. The danger with an economy so dependent on natural resources is that it is not dependent on other countries as much as manufacturing economies are, Russia has never had to cooperate to the same extent as other countries since they could just suck up more oil rather than trade manufacturing goods with other countries. The EU was perfectly fine with this arrangement until relatively recently, the EU got cheap oil and gas from it, so might as well help the Russians with surveillance equipment, money laundering, and gas pipelines. Russia being an oligarchic source of cheap oil served us well until it diden't. Now we have a big mean bully with imperial ambitions on our doorstep.