The USA dropped the ball on this. I was screaming at the news (or anyone that would listen :) ) that we needed work closer with Yeltsin/Gorbachev to support the burgeoning democracy. The USA just patted itself on the back and didn't do anything diplomatically/financially other than lip service to build economic ties and then the big collapse and rise of oligarchs and Putin.
They actually did open up relations a lot, but Russia was like Mordor and the old ways were just too ingrained. The ball was less dropped and more the air slowly deflated.
