So let's say, hypothetically, that Sheldon didn't use any of his own money to buy his shares, but borrowed money (being the good capitalist that he is). He knows that Pinetree must sell, so he sells shares also to satisfy his creditors, knowing he can buy them back cheaper due to the compounding effect of his shares being sold along with Pinetree.
Let's say he sold 2 million shares over 3 days starting at 1.10 per share. Combined with Pinetree, the effect drops the share price 25 cents. If he knows they have shares to sell and they wil do so til August 26, AND he was allowed to resign and begin trading 48 hours later, knowing that there is no insider information ( thus, no news is bad news), he could continue to sell along with Pinetree and then begin to buy back shares, say next Tuesday, to replenish his inventory at a much cheaper price. Possible he could do this with many million shares. Knowing that the fall is sell side imbalance and not fundamentally driven, would it be worth it? Maybe, especially if his selling caught Pinetree off guard and then forced them to sell more.
The only flaw in this scenario is if the company decides to announce info earlier and he gets halted out. Not likely. Just spitballing here.
