The judge is there to interpret and to apply the law. If there's a hole, there's a hole. And the incentives would be immense to find a legally defensible hole. Think bug bounty on an unfathomable scale.
When the law says "companies can't own themselves, even indirectly, or the CEO goes to jail" the judge will be able to see that company A owning company B which owns company A is indirect self-ownership, and send the CEO to jail. No matter how complicated a scheme the CEO comes up with, the judge can likely see through it.