Eh, I think a lot of the responses here are a little too deterministic. To be clear, all the points raised are valid. Soviet-era institutions, norms, and societal expectations; the post-Soviet economic shocks; the corrupt, disastrous privatizations; the conflicts with NATO over Serbia/Yugoslavia; state control over the media (which was increasing through Yeltsin's last term); the 1998 Russian Financial Crisis; democracy's weak roots in Russia: all of these made Russia susceptible to a descent back into autocracy. There was no singular moment either where democracy was fully snuffed out; it was gradual, and even during Putin's first term, there was real opposition to him in the Russian Duma.
But just because the conditions are present doesn't make an outcome inevitable. Let's not forget that the
1999 parliamentary elections in Russia, ironically the first of the Putin Era, were widely seen by observers as being the most democratic in post-Soviet Russian history. You can make a plausible argument that Putin was somewhat better-situated than other rivals to establish a dictatorial system. He became president basically by acclimation and faced very little opposition early on because he was a cipher with whom different factions all felt comfortable. (Including, ironically, Russian liberals.) His relative youth also helped. In other words, Putin was both skeptical of democracy and had the means with which to erode it. An alternative leader might have lacked one or both of these. Someone like
Yevgeniy Primakov, for example, would have hardly been a liberal leader, and in fact would likely have been somewhat more anti-Western than early Putin. But he also would have encountered wider opposition early on, making it perhaps more difficult to re-consolidate power in the Kremlin. He would also have long since passed the scene, and the result may well have been a less top down, pharaonic political system.
Now, I have a hard time seeing this as a
liberal democracy. But it isn't crazy to imagine a present-day Russia that was still somewhat corrupt, chaotic, and illiberal, but still basically democratic, with a wider number of media outlets, competitive elections, and some rotation in office. Think of most middle-income democracies (like in Latin America) or for a nearer example think Romania, Bulgaria, or Poland. (Admittedly, the last one not so hot right now.) Or in a somewhat more pessimistic scenario, Ukraine or Georgia. In fact, this is what many observers expected in the late 1990s and early 2000s, when the consensus among both domestic and international political observers was that elections had become too institutionalized in Russia for a real dictatorship to reemerge.