Originally Posted by rickg523

Well under the circumstance, knowing he's showing up on day two, the hotel could have activated his key. That would have been the decent thing to do. At the very least, if they have decided that they're in the rate-collection business instead of the hospitality business, they could have informed him of the consequences of his delay.
But not only didn't they do that, if you read the OP they rather deceptively said they'd "hold his reservation," by which it turns out, means "we'll rent you a room for nights two through five for a $1000 fee for not using the room tonight. Which we will hide from you until you check out."
It's indefensible. And no T&C makes what this hotel did right.