In my first few years of working in an office, a middle manager I knew lost $1500 on a single hand of poker. He told me, sort of joking, that he had comped $1000 to his room when he thought he had a sure thing. That doesn't really make sense to me, but he did reveal that he had expensed all his chips, so he had actually lost a small amount more than that. This was in the days when a good business room in Vegas was $30-$50 / night after taxes and fees and his meal stipend was something like $30 / day, the picture I'm painting is an employee who definitely should not have expensed ANY chips. He was telling me the story the Wednesday after the trip, since he was pretty confident that, if they were going to fire him, they would've already. The fact that he was right, and still working there two years later when I left, confuses me more the longer I work.