If x > y , the Dentist wins. Because then the judge is going to say, "You, Epiphyte, owe this poor aggrieved minority shareholder $ x . But as I look at the parlous state of the corporation’s finances I see that there’s no way for you to raise that kind of money. And so the only way to settle the debt is to give the plaintiff the one asset you have in abundance, which is your crappy stock. And since the value of the whole corporation is really, really close to being zero, you’re going to have to give him almost all of it."