In any case, Tim Berners-Lee wasn't an amateur. He was a computer scientist who had experience with information systems before creating the Web. But his design was clever AND simple and accessible to use for amateurs.

If I remember the context of the "created by amateurs" quote, it was really Alan Kay complaining that the web wasn't designed by OO principles. He wanted the web to consist of objects encapsulating their own presentation logic, rater than document in declarative languages. So basically something like Java applets instead of web pages.

While OO is great for software design, I believe declarative documents have proven to be much better as a foundation for a decentralized information system. Think about how to implement Google, accessibility, readability.com and so on in a web of encapsulated objects. And it is not by accident that TBL chose declarative languages over objects, he actually though about it: http://www.w3.org/2001/tag/doc/leastPower-2006-01-23.html

This is an example of the contextual insight you talk about, and which I believe Kay lacks in this case.

EDIT: The interview is here: http://www.drdobbs.com/article/print?articleId=240003442&sit... It is not totally clear what he is arguing, but is seems he is suggesting that the only job of the browser should be to execute arbitrary code safely, but any actual features beyond this should be provided by the objects. So the browser should really be a VM or a mini-operating system executing object code in a safe sandbox. This seem to be the philosophically opposite of TBL's principle of least power.

Honestly, it seems like Kay is ranting a lot in the interview. When something like the web is not designed the way he would have done it, the only reason he can imagine is that the designers must have been ignorant amateurs.