Earlier quoted context omitted.
Is this the one where he says the web was designed by amateurs and it should have been a virtual machine instead? He says they did a better web 30 years before or something to that effect. If so I'll commit blasphemy and say he's wronger than wrong. I was especially offended that a curious person would display such ignorance in understanding the work of others. Without going too much into detail, if he believes this,…
That exact quote is from a more recent talk of his, but he does mention the web and his current distaste for the design principles it embodies. I would encourage you to still watch the talk as it his criticism of the web is an incredibly small portion of the overall talk. I wish that you had included more substance in your criticisms so I could have either agreed with you, disagreed, or explained my interpretation of…
The principle of least power basically means that you should convey meaning across the web using the least expressive language or abstraction possible. The reason is that you want give the client more choices to interpret the data/content, rather than forcing it to correspond.
http://www.w3.org/DesignIssues/Principles.html
Google, or any other search engine, would not be possible without the principle of least power. Mobile phones wouldn't have been able to use the web if the semantics were over-fitted for specific devices.
I've heard what is essentially Kay's argument from other sources too. Some computer scientist at Adobe (may have even been one of the founders) lamented that the web wasn't build on PDF. PDF is a Turing complete language that can describe any page layout.
Certainly after one has messed with CSS enough, you can see why he would say that (aside from the obvious favoritism). But it is terrible idea, in that it overfits content for specific devices, and is a vector for malware, etc. Once you are Turing complete, it's very hard to avoid these pitfalls.
Anyway, as I recall, Kay is making essentially the exact same argument as the Adobe guy, and the way he said it in that talk (Programming and Scaling, thanks below) displays astonishing ignorance for such a brilliant guy.
If Kay is right, then he should just create a web that is based on a VM. And then he can see how far it goes. It will never go anywhere because it will be broken by design.
That we are developing more VMs now for the web doesn't negate the point. The web should be layered; each kind of content should choose the least powerful channel to transmit it. If you need arbitrary code, then the least powerful abstraction is a Turing complete VM. But you don't need a Turing machine to display a blog post.