It would be entertaining to see Trump obliterate his own legal positions in court, but I suspect we won't see it (I realize of course you're just joking).
In a somewhat different context, if a federal court instructs the U.S. Marshals to take action and Trump orders them not to under threat of termination (this would violate the law*), it's quite possible that people would resign rather than follow an order from Trump that is illegal.
Mass resignations are at least one potential check on the power of an executive branch that goes rogue.
*
28 U.S. Code § 566 - Powers and duties
"(a) It is the primary role and mission of the United States Marshals Service to provide for the security
and to obey, execute, and enforce all orders of the United States District Courts, the United States Courts of Appeals, the Court of International Trade, and the United States Tax Court, as provided by law." (emphasis added)
www.law.cornell.edu