A Literal Stifler
Imagine what it would be like working for Steve Stifler from the American Pie movies (remember those?). It would probably be the most awesome thing in the world, especially if they’re your boss. They’re not the sharpest tool in the shed, so maybe you can get by with making all sorts of mistakes at the workplace.
Well, that’s wasn’t exactly the case in the OP’s story. The Stiffler in question came from a rich family, but he was trying his best to be as “normal” as possible. It sort of makes sense if someone who’s used to seeing millions not notice a $5,000 increase in their bank account, right? They’d probably think it was just interest or something.