Monday’s oral argument in the U.S. Court of Appeals for the District of Columbia Circuit on the validity of Judge Tanya Chutkan’s limited ban of defendant Donald Trump’s pretrial free speech rights underscores the uniquely problematic nature of the most important criminal prosecution in the nation’s history.

While Chutkan’s pretrial gag order was narrowly drawn to preclude only gangsterlike attacks on prosecutors, court staff, and trial witnesses—a much narrower ban than the government had sought—the former president’s lawyers argued that absent their client’s remarks having crossed any criminal lines, the First Amendment precludes imposition of the gag order. After a notably long 2½-hour debate about where such lines can and should be drawn, and the level of threat to witnesses that must be established before a gag order can be issued, the court adjourned to consider the matter.