I pretend I’m an elder millennial, but in reality, I am a Gen X-er who came of age in the mid-to-late ‘90s. And if there’s one film that captures my suburban Southern California teen years, it’s “Clueless,” Amy Heckerling’s 1995 retelling of Jane Austen’s “Emma” via a Beverly Hills high school. I’ve seen it so many times that I’ve committed most of the script to memory, to the annoyance of my family.

And that’s perhaps how and why, as I stood, shoulder to shoulder, with other reporters in the clerk’s office of a New York state appeals court on Monday, “Clueless” immediately leaped to mind. 

But let’s rewind the VCR, so to speak. How did we all find ourselves crammed into an administrative office? 

You might remember that a four-judge panel of New York’s first tier of appeals courts last Thursday lifted the temporary stay of Judge Arthur Engoron’s twin gag orders on Donald Trump and his lawyers in the civil fraud trial against the former president and others.

And that meant that as of Thursday afternoon, Trump was once again prohibited from making any statement, whether in or outside court, about the judge’s courtroom staff, including the judge’s principal law clerk. At that time, I understood, due to the nature of the relief Trump sought and my analysis of New York court rules, that Trump would be stuck with that gag order through the duration of the trial, including his own testimony. 

Nonetheless, I was warned that Trump could always swing for the fences with some unusual legal maneuver. And indeed, by Monday morning, Trump’s lawyers filed papers essentially asking a single judge of the same court that lifted the stay to permit him to appeal that order to New York’s highest court, the confusingly-named Court of Appeals, while rushing briefing on the merits of his appeal, both by Wednesday. That would allow them time to secure relief before Trump takes the stand again on Dec. 11 — and empower Trump to rail against the clerk in the courtroom, the hallway and, perhaps most importantly, his online fundraising solicitations.

So by Monday at 3 p.m. ET, I gathered with a handful of journalists at the New York state appeals court. But rather than sitting in an elegant courtroom, we witnessed a surreal scene unfold in the clerk’s office. And the players — an assistant state solicitor general, a lawyer for the court system there on Engoron’s behalf, and Trump lawyers Chris Kise and Cliff Robert — stood at the counter as a court attorney listened from the other side. There, Kise and Robert pleaded to have their filing signed by the appellate judge on duty. They argued no issue could be more important than the ongoing deprivation of the First Amendment rights of their client.

But, the court attorney explained, their request for permission to seek relief from last week’s order was procedurally defective. Instead of seeking relief from a single judge, they should have filed a different kind of motion addressed to a full panel. But even if their filing were treated as a motion, the court attorney continued, the New York attorney general’s office had a right to respond, and under ordinary court rules, its brief would not be due until Dec. 11, the day of Trump’s planned testimony, unless the state would agree to file sooner. And the AG’s office said it would not.

Moreover, the court attorney noted the underlying appeal of the gag order could not be expedited because Team Trump already had agreed its appeal would be “returnable,” or ready for court review, on that same day: Dec. 11.

Kise seemed genuinely flummoxed. Wasn’t there someone, anyone from whom he could get a sooner hearing? We are talking about the speech rights of the former president and the GOP presidential front-runner, he noted, an urgency creeping into his Floridian drawl.  

And that’s when I remembered how, in “Clueless”, Alicia Silverstone’s character, the lovably clueless — and daughter of a litigator — Cher Horowitz, fails her driver’s license test so miserably that the examiner makes her pull over. Nonetheless, she asks, eyes wide with a mix of privilege and naiveté, whether there is someone above him with whom she can speak. The examiner gruffly responds, “Girlie, as far as you are concerned, I’m the messiah of the DMV.” She then shuffles to the passenger seat, visibly shrunk by a defeat she could not talk her way out of. 

Kise, of course, neither resembles the Fred Segal-clad Silverstone nor did he adorably whine as she did. In fact, he was far more subdued in tone than in recent courtroom battles either with the state attorney general’s team or Engoron. But when told repeatedly there was nothing his team could do to expedite either of their two imagined avenues for relief before Dec. 11, he seemed palpably frustrated a la “Clueless.” Surely, you are not the ultimate authority on this, he suggested to the civil servant before him. 

And to be clear, she wasn’t the official last word. Justice Sallie Manzanet-Daniels, who presided over the four-judge panel that reinstated the gag order last week, officially endorsed the denial of Team Trump’s application and the briefing schedule. 

But the thrust of what the court attorney told the parties from the counter of the clerk’s office remained true: Without the consent of the AG’s office and given their own delay, there was no getting a hearing earlier than next Monday. And that means Trump, to the extent that he testifies on Dec. 11, has to do so with the gag order still in place. There are no witnesses expected after him, nor can his legal team simply call a timeout until their applications are resolved. 

Following Monday’s proceedings, Kise confidently assured me and other reporters that he has no concern about Trump’s fidelity to the gag order. But Trump has already violated the order twice, earning fines each time. Meanwhile, last week, Engoron warned he will enforce the order “vigorously,” a pledge that could extend to 30 days in jail if Trump is held in contempt.

So Trump’s lawyers now have an unenviable problem: Allow their client to risk a third violation or tell the most ungovernable, independent client that he may not take the stand. And of course, had they and he made different choices along the way, they wouldn’t even be in this position; even seeking appellate relief last Friday might have obviated this mess.  

As Cher might say, “Oops. Their bad.”