Now to finish this off, If you plan a 10b5-1 while knowing that a catastrophic event is looming, is there any way to prove that as insider trading? (without obvious testimony from another person)
Let's use a biotech with a drug in a trial that is giving off obvious signs of being a dud as an example.
In view of the more recent SEC statements on this issue, I'd say this puts it too strongly. The SEC has basically said that if you do this then you potentially call the validity of the whole Plan into question, which would potentially remove the safe harbor for any other prior transactions. So such an action is not at all risk-free from a legal perspective in my view.
There would likely also be a big outcry and bad publicity. So for any reputable firm or individual I think such action is quite unlikely.