"All kinds from all over. And knowing full well how horrible it would be to work a full year Okinawa they drank. The job of the special guards was to see that they didn't tear the barracks down."
Who else was very surprised that Jack worked in a jail? He's passive as an authoritative figure, and enjoys drinking with the inmates. Maybe he was using the profession as another way to meet "mad people."
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I think Jack got the job because it allowed him to have money. He doesn't want to get to the inmates because he never has a substantial conversation with any of them. He drinks with them simply because he wants to drink and there is nothing else to do. Everyone else knew that Jack was not a real guard he saw the guards as something below him.
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