I think what he did could have passed had he not made it official by writing letters and sending them. I think he could have conveyed all this orally in an ambiguous enough way.
The reason is that once this becomes official enough and "on the books" this kind of stuff would happen again. The real nightmare is not him doing it and getting way is every disgruntled agency employee doing it and then pointing fingers at this case saying "but you negotiated with him!".
So I think he wasn't smart enough, he could have had a chance at this had he not stirred the waters that much.
Another, general way of putting it, is that in large bureaucratic institutions (officially!) you never put your superiors in a position to make a new rule or break an existing rule.
His problems started earlier, I think. A red flag came up when I saw that he ticketed the fire chief (and got fired for his trouble). Then later he kept escalating some issue above his superiors, despite being warned that his career was on the line. The guy just doesn't know his place.
I would say he doesn't know how to play the game. How you play the game is you never break the rules while you make sure people know you're not the bitch. As the person above you said, he should have made vague threats. This is negotiation 101. Government wants leverage, former employee wants leverage. They have what he wants ($), he has what they want (information).
Last time I checked this was Hacker News. One of the commonly accepted meanings of 'hacker' is someone who challenges the existing order and power structures. You won't find many friends here with this attitude.
Last time I checked this article was about the CIA. One of the commonly accepted jobs of 'CIA' is someone who maintains the existing order and power structures. You won't make many friends in he CIA if you go against it.
The reason is that once this becomes official enough and "on the books" this kind of stuff would happen again. The real nightmare is not him doing it and getting way is every disgruntled agency employee doing it and then pointing fingers at this case saying "but you negotiated with him!".
So I think he wasn't smart enough, he could have had a chance at this had he not stirred the waters that much.
Another, general way of putting it, is that in large bureaucratic institutions (officially!) you never put your superiors in a position to make a new rule or break an existing rule.