> Not entirely - they link to a lot of cached stuff that isn't out there any more.
Google caches web pages, but after the original web page is taken down, the Google cached copy will disappear some time later. i.e. Google does not keep copies of pages available that it knows no longer exist. If it did, it would knowingly be sending searchers to "Error 404" pages, and that wouldn't be a good searcher experience. It does not do that. This ruling isn't about cached pages, it's about links to actual pages on the web.
> The fact that the stuff is out there is also confirmed by things like the wayback machine
No, the wayback machine has its own cached copy, and Google does not index that. In other words, you won't find things that are only in the wayback machine in Google's search results.
That's not to say generally that Google won't index some other cached copy but when, it comes down to it, in many cases there's little difference between a cached copy and the original. If you're searching for something, and Google knows a page that's relevant, it may well recommend that page and that's what Google's searchers want it to do.
What this case is really about is WHERE in the search results a particular page is listed, as if these newspaper articles were not so prominent it wouldn't really be an issue. The guy is saying "Newspaper articles from 16 years ago aren't really that relevant." His problem is that he hasn't done anything particularly noteworthy since. If there were over 100 more recent, more "relevant", results for his name then his past misdemeanours would be buried.