Smart people are pretty quickly able to identify gaps in a process (and there are always gaps). Jaded people realize that nobody really cares what you do, good or bad; all that matters is hitting the metrics. And cynical people feel entitled because of what they've been through ("I gave my life to this company, and they don't appreciate it...").

The higher you are in management, the more you have of all of those traits. Theft and fraud are so pervasive and most managers get away with it for years. Even if they are caught, at worst, they are merely fired.

The more Machiavellian-types rope in low-level employees. So while it might seem like a "gang" of 20-somethings at an electronics store made off with a shipment. The reality is, an upper-level manager provided the cover for them to do so, and knew how to leave just enough evidence that it was an inside job, but not enough for the police to bother. For example, the badge used to access the storage area might belong to a little old lady who is honest to a fault and would be readily identified by security cameras. And if anyone questions why the store greeter has such privileged access, then it was just an honest mistake.