Gifting shares is also a change of ownership, which means reporting it. I'm not saying he won't do some Jew trick. Off the top of my head, he has the next CEO lined up as his replacement, who will be in on the scam coming up: Between reporing periods, and with enough time out of the company to just sell all of shares, he does so and triggers a capital loss.. He collects his cash and then leaks his story of selling the shares to a reporter. Everyone sees the story and dumps their shares, sending the share price in free fall. When it hits the bottom, the former CEO buys a buttload of shares (maybe all of them). The new CEO comes out in the next couple of days, just after that recent reporting period, and tells everyone "our sales are X and we're in a REALLY good financial position, I have just implemented a policy of only hiring all positions based on merit and competency, so we will find and fix all of these issues before any more happen". People see this an opportunity and then start wanting to buy the stock. The new CEO lists his shares for sale above the highest price being offered, someone buys that lot of shares (really the former CEO did from another account, so he just drove up the price). He repeats this multiple times until he gets price to where he wants it to be then starts selling for real, the shares he bought for $0.05 he is now selling for $50.00. He just turned his millions into billions.