Trump must be his lawyer's nightmare: He is constantly undermining any legal suit he has a part in. They go to all the trouble to create some fanciful justification for their case, and then he goes on twitter and craps all over it. His fans may be stupid enough to believe two (or more!) mutually exclusive things at once, but judges make a career of never doing that. Trump makes the common mistake of assuming judges are no smarter than he is.

John Roberts is willing to suspend belief and accept a ridiculous legal theory, but not when Trump can't bother to stick with just one lie.