That sucks, seems like a breakdown in communication, misinterpretation of the rules and logistics getting in your way.

I hope that his ongoing ticket from WAS is okay and that they didn't cancel the whole thing when he didn't board in ANC - fingers crossed.

I would ask for 50K in miles as compensation. You probably won't get it, but its what I think is reasonable. That said, there are errors here on your behalf -- I'm sure it seemed reasonable for you to carry his passport AND the gate agent could probably have made it work (despite the computer insisting for travel information) but you were carrying his documents.

good luck!