On the contrary, his only mistake was that he didn't see that the naive idealistic pseudo-democratization which co-opts the people's creativity to become conduits for advertising is one and the same as corporate capitalism.
I think Wikipedia, Wikileaks, the use of Blogs, Twitter and even the epitome-of-corporate-antiprivacy that is Facebook by political movements: all present very strong counterevidence to your claim that the web has not been democratized.
The heart of any information medium has to be commerce, in that there has to be way to economically support the infrastructure costs of the medium but what makes the web more democratic is:
1) The infrastructure costs are very low and falling (The cost of a web server that you can run two hundred blogs off is not more than $200 / year)
2) Quite contrary to what Jobs claimed, everyone on the web is already a publisher.
Another example of this is restaurant reviews. The basic argument is familiar: a single restaurant reviewer in a newspaper is an elite, and this creates the potential for abuse of power. He could demand kickbacks from restaurants to ensure positive reviews or promote his friends' restaurants at the expense of competitors, and so on. Decentralization is proposed as the solution: instead of a single restaurant review, individual patrons review restaurants on a web site and it averages the reviews, and even if a few of them are corrupt, it's much harder to subvert the system. So problem solved, it's a much more trustworthy system. Except for one minor problem: Yelp implements this idea, and restaurant owners have complained that Yelp has abused their power by trying to extort advertising dollars from them by threatening to delete positive reviews and post negative reviews.
The pattern should be clear: moving from a centralized system to a decentralized network doesn't eliminate power, it just moves it to a different place where it can be potentially abused by a different group of elites. That position of power comes from controlling the protocol which aggregates each individual node on the network. The nodes can be decentralized and distributed, but the cost for this is that they must all speak the same language to connect to each other, which is a centralization at a different level.
That's why further decentralization doesn't solve the Yelp problem. We could imagine a federated system of restaurant reviews where individual reviews are stored on servers controlled by individuals, so they can't be deleted. But this just moves the power to a different level - the system for aggregating the peers on the node becomes the position of power, which could potentially be exploited for power and money to an elite. A similar relationship exists between Facebook and Diaspora. This is why Google promotes decentralization, because it is the centralized place you have to pass through in order to get to all that decentralized content, and there's lots of money to be had in owning that position. The handful of multinational corporations that control the internet backbones are also in a similar position of power, control and profit. This is ideal position to hold power, because the average person is completely clueless that these are positions of power. Think of how few people are aware of the importance of network neutrality, for example. Evgeny Morozov makes similar points in his TED talk entitled "How the Net aids dictatorships."
Really, the people promoting decentralization as a moral imperative are the ones who are profiting from it, from VC backed startups who stand to make millions or even billions of dollars to global multinationals who already are. Here again, the idealistic hacker ethos and ruthless corporate capitalism turn out to be one and the same, a nice example of the Hegelian coincidence of opposites.
The fact is, if you go use the "edit" button right now and make a good-faith improvement, your edit is overwhelmingly likely to stand.
The "oligarchy" you refer to consists of many hundreds of people, freely nominated from among all the site's users, elected by the votes of every Wikipedia user. If you've made just a few edits, you can OK or neg new members of the "oligarchy".
What you're of course ignoring is the fact that Wikipedia's overwhelming success at their original mission has resulted in a ridiculously valuable position in everyone's search results and a huge influx of random users. I'm not a fan of the bureaucracy at all, but I at least respect the abuse, misuse, and obnoxiousness they're up against.
It's amazing to me that they're as good as they are. They certainly aren't some weird mindfuck or exploitation scheme, as you seem to be implying.
This logic of "Democracy is great! But of course we have to have some standards..." has been used to conceal elite power for centuries. In the US, political participation was originally reserved for white, male property owners, because it was thought that the standard for voting is rationality, which women and lesser races don't have. The elites permit democracy, but they reserve the right to decide what the standards for participation should be. Who decides what "good-faith" means? This isn't conspiracy, it is ideological delusion: elites become corrupt because they're convinced of their own benevolence, that because they stand for Democracy and Decentralization (today's empty signifiers, replacing God, Nation), preserving their elite position is justified. It is definitely not because they cynically manipulate, pulling the strings behind the scenes while laughing at the deluded masses. It's a natural human tendency to see yourself as acting only for the greater good, and to adopt an ideology that explains why what's good for you is good for all.
As I mentioned before, my preferred solution to elite power is not some fantasy of "true democracy", which only ends up concealing real power. Nor do I think that elite control is necessarily a bad thing, only concealing elite power behind mask of democracy. Scientific knowledge is an obvious arena where we are best served by having an elite. But if they abuse their power, we should be ready with the (metaphorical) guillotine. In the case of Facebook, the real response is not a different, more decentralized system, but the guillotine of strong privacy regulations. Or government enforcement of net neutrality, and so on. The libertarian & anti-government leanings of the tech community is more evidence in favor of my argument. Is this not just another way to defend an oligarchy? I think many sincerely believe that this is the best arrangement, but avoiding the facts might cast some doubt on this.