Imagine you have a million Bitcoins and the price goes to 1000$ and more. Wouldn't you or any normal person sell at least some part of it? Don't tell me he doesn't care about money or he wants to wait for a higher price. This makes no sense.
What price anonymity? Only he can tell you what value it has for him.
A $1000 price means thousands of people will be constantly scanning his known coins for signs of life. As soon as something did twitch people would be going all out to find out where they were headed. He couldn't use any type of exchange for fear of being dug out. He'd be depending on exchange owners to be secure and they don't exactly have a great track record nor could they resist digging around either.
You couldn't use them to pay for a product because it has to be shipped somewhere. You couldn't buy anything digital just in case it's been marked somehow. He kind of scuppered himself a bit.