Playing to the theme of the thread, the drug use and gay activities ensure that he will be compliant to his handlers demands on pain of having that more "out" than most observers already understand. He is too valuable as a tool to manipulate right now to "out" him. When he leaves office, there will be little reason to protect him.
Outstanding observations on all points. I doubt he considers himself such an urchin, though, and instead imagines everything that has been dumped in his lap as simply his due.