Most Epic Benchslap Ever: Fifth Circuit Orders Judge Booted From DEI Case Over AI

Oct 23, 2026 10:40 AM
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Most Epic Benchslap Ever: Fifth Circuit Orders Judge Booted From DEI Case Over AI
AP Photo/Patrick Sison, File

When does "artificial intelligence" cross the line to organic stupidity? Judge Henry Wingate just found out the hard way. The Fifth Circuit has taken the extraordinary step of ordering his removal from a case it remanded for reconsideration by an actual judge, after Wingate screwed up not one but two rulings through the use of AI ... and incompetent judgment on top.

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Courthouse News Service reported the story late yesterday, as did Reuters behind its paywall. Wingate had issued TROs preventing the enforcement of a new Mississippi law that prohibits the use of DEI policies in public education. However, his first TRO relied on an AI review of case law that turned out to be in error, at which point Wingate imposed another TRO that was just as faulty (via Instapundit and Will Chamberlain):

In a scathing opinion, U.S. Circuit Judge Jerry Smith criticized U.S. District Judge Henry Wingate, a fellow Ronald Reagan appointee, for his rulings finding a group of teachers, students and parents were likely to succeed in their claims that the law violates the First Amendment and is unconstitutionally vague.

The panel ordered that the case be assigned to a different judge on remand, finding that Wingate had based his decision “on impoverished legal analysis that barely paid lip-service to the precedents of the Supreme Court or this court, seeming at times purposely to misconstrue the law by manipulating the words of statutes and cases, without regard to their texts’ meaning as a whole.”

The panel noted factual errors in a temporary restraining order that appeared to be the result of AI hallucinations, including naming plaintiffs and defendants who were not parties to the case, quoting terms that did not actually appear in the act and citing evidence not in the record.

Amazingly, Wingate tried to correct the AI record with what appears to be another AI hallucination:

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When U.S. Senator Chuck Grassley, an Iowa Republican, accused the court of having used AI to write the temporary restraining order, Wingate acknowledged the use of artificial intelligence, claiming a law clerk had used AI to write a draft of the order that was mistakenly docketed.

While Wingate issued a corrected version of the order, the panel noted that version contains a citation to a non-existent case that appears to be another AI hallucination. The judges found this was also problematic for a subsequent preliminary injunction Wingate had issued.

Needless to say, the Fifth Circuit panel reviewing the case did not find this amusing in the least. The result, Will Chamberlain comments, is "the most vicious benchslap I've ever seen in an appellate opinion." In his written opinion overturning all the TROs, Judge Jerry Smith ordered Wingate removed from the case entirely, and suggested that the next judge stick to the law, the facts, and human intelligence.

First, Judge Smith lays out the bizarre path the case took to this review:

The proceedings in the district court were a botch job, to say the least. Judge Henry Wingate issued a temporary restraining order (“TRO”) enjoining enforcement of H.B. 1193 that contained several factual assertions nowhere to be found in the record, or indeed, in any proceeding of the case. Those included mention of plaintiffs and defendants not in the complaint, supposed “declarations” from non-existent or never-present individuals, false quotations purporting to be taken from the text of H.B. 1193, and several erroneous claims that the law had already led to the demise of apparently fictitious programs.

After this came to light, Judge Wingate replaced the TRO without explaining. 

Forging forward despite the bungled TRO, Judge Wingate issued a pre-enforcement preliminary injunction. The various state defendants appeal.

At oral argument in this court, it was discovered that even the “corrected” TRO—which was incorporated by reference into the preliminary injunction order—still contained hallucinated information (namely, a citation to a purported Fourth Circuit case, “Cousins v. School Bd. of City of Norfolk,” that does not exist).

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Smith blasts Wingate in direct and unmistakable terms for his incompetence and dishonesty:

This district judge carelessly exercised his Article III power by issuing sloppy edicts based on falsehoods and fabrications. Upon discovering some of these falsehoods, Judge Wingate dug in his heels and claimed that the hallucinated claims had no bearing on its reasoning; he offered no explanation as to why he included such apparently irrelevant material in the original TRO or why the TRO nevertheless was justified in its absence.

Moreover, the district court got the law wrong. The TRO and preliminary injunction order rested on impoverished legal analysis that barely paid lip-service to the precedents of the Supreme Court or this court, seeming at times purposely to misconstrue the law by manipulating the words of statutes and cases, without regard to their texts’ meaning as a whole. The district court—or perhaps, being charitable, its AI agent—ignored and manipulated governing law, apparently to satisfy a policy agenda.

The ruling essentially fires Wingate from the case:

Because of the extraordinarily grave errors by the district court, we vacate and remand for assignment to a different district judge. Per the Supreme Court’s decision in Moody, we instruct the new judge to conduct proceedings consistent with federal law as interpreted by the Supreme Court and this circuit. 

Smith uses the rest of the ruling to go into detail on all of these points. The summary above that leads the opinion is sufficient to grasping the technical issues Smith explores. This is a unanimous ruling, although the concurrence from Judge Haynes suggests that he thinks there's more to the underlying complaint:

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I concur in the last paragraph of the majority opinion. I think it is important on the remand to take a more full look at the House Bill 1193 in play. I also think it is very important to make sure that teachers at school are in no way limited or forbidden from teaching the students not to discriminate as set out in Title VII, including race, color, religion, sex, gender, etc. 

Haynes raises no opposition to booting Wingate off the case, nor to the characterization of his competence and integrity. 

What makes this most frustrating is the string of scandals already extant in the legal system over AI. In just one year in the UK alone, nearly four dozen cases of AI misuse were filed. The issue may be worse in the US, where "big law" firms like Morgan & Morgan and Sullivan & Cromwell have been sanctioned over filing claims filled with AI "hallucinations." Judges and their clerks are supposed to provide checks against that issue, not contribute to it. 

Now Wingate has gotten a public humiliation over his incompetence. Want to bet that the Fifth Circuit will apply extra scrutiny to Wingate's rulings on appeal in the future? The rest of the judges in the Fifth Circuit's jurisdiction should get the message as well. Perhaps that will penetrate human intelligence in the future, and limit the use of AI. 

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