I am wondering if there could be a way to outsmart the system. Perhaps trades are monitored automatically and once flagged for suspicious timing and returns, th

I am wondering if there could be a way to outsmart the system. Perhaps trades are monitored automatically and once flagged for suspicious timing and returns, they are reviewed manually. What if someone was trading in a smart way, e.g. purpusfully accepting losses on the same stock/derivate, trading during non-blackout periods, focusing on more than one stock excessively. This could reduce the risk for automatic detection. And finally, when you are reviewed manually, you should be able to present some fancy excel models that you pull out your ass to support your "buying decisions" when you made the insider trading moves. The biggest thing would be, however, to keep your partner in crime at distance so there is not obvious evidence that you spoke about trading. I wonder how hard it is to outsmart the system and I can imagine that there are many people out there who play it very well.