Mikhail Gorbachev has died

The United States didn't do enough to help Russia transition to democracy in the 1990s. There was no "Marshall Plan" after the Cold War like there was after World War II. This was a huge mistake, and we see the consequences now, with Russia having turned back toward totalitarianism and imperialism. Sadly, it seems that Gorbachev's efforts were mostly for naught. But it was courageous at the time to open up the Soviet Union to glasnost and perestroika.

Of course Yeltsin was a big part of the problem too.

The locals in power have to want to do it too. As soon as enough don’t want it, it is over.

I’m skeptical of the idea that you can impose Democracy.

You can't impose democracy, but if democracy and associated ideas such as the free market spectacularly fails the people – as it did in the 90s – then that certainly doesn't help. We probably could have done a thing or two to make it fail less. Would that have made a meaningful difference? Hard to say for sure, but it would have been worth to try.