If they tried that they'd be tied up in court for years.
Theoretically, they could change the lockup period, or authorize more stock and have a shelf offering to pay him a dividend... but in either case they'd be sued immediately by the other shareholders.
He's cheat/crafty/cunning. As you know not as silly as many think he is.
You give him too much credit. Shittypants is a demented moron. What he does know, is how to hire people to do the thinking for him. He's done that forever, hire people then rip them off. There is no way he is capable of that business thought process, he's too locked in his one track presidential saving mode.
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