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> They may have been thinking they could make >$5-10M on trading options on insider knowledge on upcoming OpenAI deals (or ending thereoff)

I agree he may have been thinking that, but it's another sign this guy was not the sharpest tool in the shed. I'm not an expert myself but was once stranded in an airport with an F500 CFO who definitely was. That's when I learned it's surprisingly difficult to make millions of dollars trading on insider information. While you can definitely make the trades, the hard parts are:

1. Getting away with it. Making a lot of money quickly requires being right when almost everyone else was wrong, which is easy for watchdog algorithms to spot. And if you work for a company involved in the transaction you're already on a watch list, so you have to enlist someone else you really trust as your accomplice to make the trades in their name - and it really helps if they're someone who has an existing history of making this size and kind of trade. Otherwise, your accomplice's name will automatically start at the top of the suspect list for investigation.

2. You need the right kind of actionable opportunity to come along. Transactions for which insider info could let you double or triple your money in one deal are pretty rare. More than that usually requires leveraging yourself up or having a lot of cash to put at risk. Unfortunately, the nature of insider info is it's about transactions which can end up being delayed or not happening at all at the very last minute for random reasons. So 'going big' with cash or leverage usually comes with a >~10% chance you could lose that cash or whatever assets you borrowed against.

Yes, it's potentially possible for an expert to find or engineer exactly the right kind of oppty, already have the resources required, and to have already prepared the mechanisms needed to get away with it undetected. But if you're that person, you already know all this. This CFO had been at the nexus of insider info for 14 years and could only think of one instance where he might have made big money trading on info he had, and that one blew up 6 hours before the announcement when the CEO of the acquisition target was randomly arrested in a prostitution sting (partying too early I suppose).

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