Let's say you are a board member or CEO of a company whose stock is due to tank badly and you can't sell it legally because of insider trading laws. Well, there is a work around called DIVORCE: reddit.com/r/wallstreetbets/comments/aeb3nq/how_to_insider_trade/ Lou Pai an officer of ENRON knocked up a striper and got a divorce just before the company's stock went into a death spiral. The divorce court actually made him to sell the stocks. He sold at $72, 4 months later the stock was at $1. Timing is everything. He made 270M and although later he was fine 31M, and he had to share the 270M, he still came out way ahead: "So, let's do the math. Allegedly made $270mil. Forced to liquidate shares for a divorce, 270/2=135mil. Settled with the SEC (probably "'no admission of wrongdoing", but barred from being a boardsitter for five years) for $31.5 mil. Walk away with ~100 mil (after legal fees, which were probably at least a couple of million). Not bad for a decade and a half's worth of "work"." "He sold his stock at $72, two months later it was $15, four months later, it was $1 and they filed for bankruptcy soon after"