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A federal judge has been removed from a challenge to Mississippi’s anti-DEI law after the Fifth Circuit called his handling of the case a “sloppy job,” pointing to orders riddled with factual errors, apparently AI-blown case citing and misapplications of Supreme Court precedent.
In an opinion written by Reagan-appointed Judge Jerry Smith, the appeals court vacated Reagan-appointed Judge Henry Wingate’s preliminary injunction blocking the law and ordered the case reassigned to another judge — an “extraordinary” and “rarely invoked” decision.
“This district judge negligently exercised his Article III power by issuing sloppy decrees based on lies and fabrications,” Smith wrote, adding that “the district court — or perhaps, being charitable, its AI agent — ignored and manipulated existing law, apparently to satisfy a political 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 filed suit, 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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University of Louisville students are holding a rally to protect diversity, equity, and inclusion (DEI) on their campus in March 2024. (Clare Grant/Courier Journal / USA TODAY NETWORK / USA TODAY NETWORK via Imagn Images)
Wingate replaced the order just two days later after Mississippi officials pointed out major factual errors, including 11 people and organizations identified as plaintiffs who were never part of the case, two officials wrongly named as defendants, and unsubstantiated claims that three schools had already canceled DEI programs because of the law.
The original TRO also cited purported statements from four individuals that appeared nowhere in the record and “may not even exist,” according to the Fifth Circuit. He also attributed language to the bill that does not appear in the law, including references to “racial or sexual stereotyping,” “racial or sexual scapegoating,” “critical race theory” and “institutional bias.”
“We are grateful – and even fortunate – that 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 out of public view,” Smith wrote.
Humans use laptops and computers to interact with AI, helping them create, code, train AI or analyze big data with fast and cutting-edge technology. (Getty Images/Wanan Yossingkum)
Even the corrected TRO contained errors, including a citation of 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 also part of the shoddy reasoning of the preliminary injunction.”
Wingate later admitted that a lawyer used artificial intelligence to help draft the TRO, following accusations of AI use that surfaced publicly. Wingate said the errors were “material” and did not affect the court’s “fundamental legal reasoning or final judgment on the merits.”
The Fifth Circuit rejected this explanation, wondering “how so many erroneous facts could not, at least marginally, ‘affect’ the ‘fundamental legal reasoning’ or support of 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, overstepping the bounds of court injunctions, and mishandling legal protections for government and public official speech.
The panel focused on the Supreme Court’s 2024 decision in Moody v. NetChoice, which establishes a two-step test for courts considering First Amendment challenges seeking to strike down a law entirely.
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Under Moody’s analysis, a court can strike down an entire law on the basis of the First Amendment only if its unconstitutional applications far outweigh its constitutional applications. The appeals court took issue with Wingate’s description of the Moody framework as “supposedly” required.
“The fact that Judge Wingate twice refers to Moody’s 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 respecting the Supreme Court’s binding authority is further reason to condemn the preliminary injunction,” Smith continued.
The appeals court also faulted Wingate for his reasoning in granting preliminary relief, pointing to his decision that the court “should pause in the face of a volatile area with such dire possible consequences.”
“This completely sets back the entire law on injunctive relief,” Smith wrote.
“A preliminary injunction cannot be sustained simply because there is a possibility of success on the merits,” Smith continued.
The appeals court also accused Wingate of misinterpreting the Supreme Court’s 2025 decision in Trump v. CASA, which prevents judges from issuing orders beyond what is necessary to protect people who have filed a lawsuit.
Wingate cited CASA in concluding that injunctions like the one submitted to him “should be all-or-nothing restitution.”
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“This is almost the exact opposite of what CASA says,” Smith wrote. “The portion cited was the Supreme Court warning against too broad a remedy and urging judges to tailor the remedy to what is absolutely necessary and nothing more.”
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The Fifth Circuit sent the case back to the Southern District of Mississippi, where a new judge will review it.
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