The way the experts play is by mutually assured destruction. You get enough blackmail material on someone to assure their cooperation, and you leak just enough to them for them to think they have some leverage over you.

That's why fraternity initiation rituals are usually at least embarrassing, sometimes humiliating, and maybe even illegal. Rather than ensuring cooperation using intimidation by strength and the constant threat of swift and certain retribution, as with organized crime's code of silence, that mutual blackmail ensures that whomever it is that acts against the group first loses most. The renegade can be dogpiled, discredited, and disavowed, and the damage to the group is minimized, because no one person can know all the dirty secrets.

If you want to take on the government, you have to be as clean as possible, while also knowing where a few of the bodies are buried. But in that case, it may be easier for the government to recruit you to switching to their side. So you also need the moral fortitude to put principles over huge, heaping piles of money. And in that case, how did you get to be CxO of a big company, again?

The proliferation of fake crimes like insider trading gives the state discretion to imprison anyone for basically political reasons. Any executive who owns financial instruments that refer to the firm that employs her can be found guilty of insider trading, if federal prosecutors wish.