It's worth noting that Nokia have had self-updating operating systems (ie. over-the-air) for years now. Admittedly, I wouldn't expect it to get much of a note in this article, but it's definitely not something that nobody has pulled off yet.
My Motorola phone did OTA updates 10 years ago. As gruber pointed out, that is likely to be the first to go from iTunes.
What he doesn't mention are the reasons Apple doesn't need to cut the cord- it helps their ecosystem. I need to install iTunes (and maybe Quicktime, maybe I check out the iTunes Store, maybe I'm doing it on my Mac). I'm sure the future is headed towards iOS devices that don't need a PC, but the alternative right now is not as painful for Apple as it is for consumers. And truth be told, plugging in a USB cable once in a while is not that painful for me either.
