Earlier quoted context omitted.
>high ranking executive risking a jail term to avoid losing 50k of stock is (again IMO), absolutely irrational. You act as if this is a real senario and would have a non-negligible probability of occurring.
There is a non-negligible possibility of this occurring. Insider trading is ridiculously easy to prosecute (the market is closely monitored) and the government regularly seeks prison time for executives. Rich people go to jail all the time for it.
Is that true? What do you mean by "all the time"?