A federal judge was removed from a challenge to Mississippi’s anti-DEI law after the Fifth Circuit blasted his handling of the case as a “botch job,” pointing to orders riddled with factual errors, an apparent AI-hallucinated case citation and faulty applications of Supreme Court precedent.
In an opinion penned by Judge Jerry Smith, a Reagan appointee, the appeals court vacated Reagan-appointed Judge Henry Wingate’s preliminary injunction blocking the law and ordered the case reassigned to a different judge — an “extraordinary” and “rarely invoked” move.
“This district judge carelessly exercised his Article III power by issuing sloppy edicts based on falsehoods and fabrications,” Smith wrote, adding that “the district court—or perhaps, being charitable, its AI agent—ignored and manipulated governing law, apparently to satisfy a policy agenda.”
The controversy surrounding Wingate’s handling of the case began with serious errors in a temporary restraining order he issued in July after a group of teachers, parents and students sued, arguing that a Mississippi state law restricting DEI-related practices in public schools and universities violated the First and Fourteenth Amendments.
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Wingate replaced the order just two days later after Mississippi officials flagged major factual errors, including 11 individuals and organizations identified as plaintiffs who were never a part of the case, two officials incorrectly named as defendants and unsupported claims that three schools had already canceled DEI programs because of the law.
The original TRO also cited purported declarations from four people who did not appear anywhere in the record and “may not even exist,” according to the Fifth Circuit. It also attributed language to the bill that does not appear in the law, including references to “race or sex stereotyping,” “race or sex scapegoating,” “critical race theory” and “institutional bias.”
“We are grateful—and, indeed, lucky—that the defendants provided a copy of the original TRO as an exhibit in their July 28 motion, ECF 58-1, given that Judge Wingate kept it from public view,” Smith wrote.
Even the corrected TRO contained errors, including a citation to a nonexistent case that the Fifth Circuit called “an apparent AI hallucination.” Wingate cited the purported case while discussing the relationship between temporary restraining orders and preliminary injunctions, leading Smith to conclude that the fabricated citation was “arguably part of the shoddy reasoning of the preliminary injunction, too.”
Wingate later acknowledged that a law clerk had used artificial intelligence to assist in drafting the TRO, following accusations of AI use surfacing publicly. Wingate said the errors were “clerical” and did not affect the court’s “core legal reasoning or the ultimate judgment on the merits.”
The Fifth Circuit pushed back on that explanation, questioning “how so many mistaken facts could not at least marginally ‘affect’ ‘core legal reasoning’ or support for the judgment on the merits.”
The Fifth Circuit found major flaws in Wingate’s legal reasoning, accusing the judge of misinterpreting Supreme Court rulings on free speech challenges, exceeding the limits of court injunctions and mishandling legal protections for government and public-employee speech.
The panel zeroed in on the Supreme Court’s 2024 decision in Moody v. NetChoice, which sets a two-step test for courts considering First Amendment challenges seeking to strike down a law entirely.
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Under the Moody analysis, a court can strike down an entire law on First Amendment grounds only if its unconstitutional applications substantially outweigh its constitutional ones. The appeals court took issue with Wingate describing the Moody framework as “supposedly” required.
“That Judge Wingate twice refers to the Moody framework as ‘supposedly’ required calls into question whether he even tried in good faith to follow the law,” Smith wrote.
“The district court’s laxity in observing the binding authority of the Supreme Court is yet another reason to doom the preliminary injunction,” Smith continued.
The appeals court also faulted Wingate for his reasoning in granting preliminary relief, pointing to his ruling that the court “should pause when faced with an unsettled area with such dire possible consequences.”
“That gets the entire law of injunctive relief completely backwards,” Smith wrote.
“A preliminary injunction cannot stand just because there is a possibility of success on the merits,” Smith continued.
The appeals court also accused Wingate of misreading the Supreme Court’s 2025 decision in Trump v. CASA, which limits judges from issuing orders that go beyond what is needed to protect the people who filed the lawsuit.
Wingate cited CASA in concluding that injunctions like the one before him “should be all-or-nothing renditions.”
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“That is almost exactly the opposite of what CASA says,” Smith wrote. “The quoted portion was the Supreme Court’s cautioning against overbroad relief and urging judges to tailor relief to what is absolutely necessary and nothing more.”
The Fifth Circuit sent the case back to the Southern District of Mississippi, where a new judge will consider it.
