Overview [1]

Henry Travillion Wingate was born in Jackson, Mississippi, on January 6, 1947. He earned a bachelor’s degree from Grinnell College in 1969, and a J.D. from Yale Law School in 1972.

Wingate launched his legal career by serving as a law clerk with Community Legal Aid in the city of Jackson from 1972-1973.

In 1973 as well, he worked as a private-practice attorney based in Jackson,

From 1973-1976, Wingate was a Lieutenant in the U.S. Naval Legal Services Office, where he worked as a senior assistant defense counsel from 1973-1974, and as a trial counsel from 1974-1976.

From 1975-1983, he was an adjunct faculty member at several different schools:

• 1975-1976: Golden Gate University
• 1976: Tidewater Community College
• 1978-1983: Mississippi College School of Law

From 1976-1980, Wingate was a Special Assistant Attorney General in Mississippi.

From 1980-1984, he was an Assistant District Attorney in Mississippi’s Seventh Judicial District.

From 1984-1985, he was an Assistant U.S. Attorney for the Southern District of Mississippi.

On September 11, 1985, President Ronald Reagan nominated Wingate for a judgeship with the United States District Court for the Southern District of Mississippi. Thirty-five days later, Wingate was confirmed on a voice vote of the U.S. Senate. He has held this District Court position ever since, including a period from 2003-2010 when he was the court’s Chief Judge.

Careless Use of Artificial Intelligence to Create a Pro-DEI Ruling Rife with Serious Errors

In 2025, Judge Wingate played a key role in determining the fate of House Bill 1193, a recently passed Mississippi state law that:

• barred public educational institutions from creating or funding any offices, programs, or staff positions tasked with advancing Diversity, Equity & Inclusion (DEI) policies;[2]
• made it illegal for educational institutions to require or consider diversity statements when making decisions on student admissions;
• made it illegal for educational institutions to require diversity training for staff hires;
• restricted the teaching or endorsing of “divisive concepts” such as those “promoting transgender ideology, gender-neutral pronouns, deconstruction of heteronormativity, gender theory (or) sexual privilege”; and
• mandated that students be taught that biological sex is determined exclusively by chromosomes and not by how a person subjectively “feels” or “identifies.”

After being passed by the Mississippi Legislature in April 2025, HB 1193 was challenged in June 2025 by the following plaintiffs:

• the Mississippi Association Of Educators
• United Campus Workers Southeast Local 3821
• Fostering Lgbtq+ Advocacy, Resources, Environments (FLARE)
• Women in Science and Engineering

The defendants included:

• the Board of Trustees of State Institutions of Higher Learning
• the Mississippi Community College Board
• the Mississippi State Board Of Education
• the Mississippi Charter School Authorizer Board

Also in June 2025, Judge Wingate was assigned to preside over the case.

The plaintiffs’ complaint – dated June 9, 2025 — read, in part, as follows:

• “Under this law, known as House Bill 1193 of the 2025 legislative session, history teachers will be banned from discussing slavery, the Civil War, discrimination in the past and present, the civil rights movement, the women’s suffrage and women’s rights movements, the LGBTQ rights movement, and many other aspects of American life and life throughout the world. Constitutional law professors must excise from their textbooks and lectures all references to the Fourteenth Amendment and cases about discrimination. Courses in family law, sociology, and biology must avoid discussions of differences and different treatment related to sex and gender identity. Teachers of English Literature must remove from their reading lists, and school librarians must remove from their shelves, works by authors like Richard Wright, Toni Morrison, William Faulkner, Rita Mae Brown, and many, many others.”
• “In addition, the law prohibits all public-school educators, and possibly students, from ‘engag[ing]’ in a number of so-called ‘divisive concepts’ relating to race, sex, color, gender identity, sexual orientation and national origin that would effectively ban discussion of certain viewpoints concerning affirmative action, unconscious bias, and collective responsibility.”
• “The prohibitions of the act come with open-ended and potentially severe consequences for any violations. Schools are required ‘to cure all actions relating to the violation,’ but the law provides no specifics on what constitutes a ‘cure.’ Given that most ‘violations’ of the free speech restrictions are likely to come from teachers and students, and that no language in the bill states otherwise, it is reasonable to conclude that teachers can be disciplined and even terminated and students can be disciplined and even expelled as part of a school’s ‘cure.’ Moreover, if a school violates the law with respect to two or more specific violations, ‘the State of Mississippi shall withhold the disbursement’ of ‘any and all funds appropriated by the Legislature’ for the particular university, community college, junior college, or K-12 public school at issue. Without state funding, the school would likely close, all students would be sent home, and all teachers and all other employees would be terminated.”
• “This far-reaching and draconian law contains viewpoint-based and content-based restrictions and violates the First Amendment rights of educators and students to free speech and to speak and learn about the prohibited subjects, the First and Fourteenth Amendment rights of educators and students to engage in their jobs and their education without concern that they might violate some of the vague and incomprehensible provisions of the law, the Fourteenth Amendment equal protection rights of educators and students to speak and learn specifically about ‘issues related to race, sex, color, gender identity, sexual orientation or national origin,’ and the Fourteenth Amendment due process rights of students to go to school[,] and [of] employees to work at schools[,] without the funding being cut off because of two purported violations of this law that those students and employees did not commit.”

The allegations cited above were replete with misrepresentations and distortions of HB 1193, as evidenced by the substance of the following key excerpts from the actual text of the bill:

• “The purpose of this act is to prohibit public schools and public postsecondary educational institutions from taking certain actions and engaging in discriminatory practices.  This act seeks to ensure that employment, academic opportunities, and student engagement are based solely on individual merit, qualifications, and academic performance, without consideration of an individual’s views on diversity, equity and inclusion (DEI).”
• “‘Divisive concepts'” are concepts that: (i)  One (1) race, sex, color, ethnicity, gender identity, sexual orientation, religion or national origin is inherently superior to another race or sex; (ii)  An individual, by virtue of his or her race, sex, color, ethnicity, gender identity, sexual orientation, religion or national origin, is inherently racist, sexist or oppressive, whether consciously or unconsciously; (iii)  An individual should be discriminated against or treated adversely solely because of their race, sex, color, ethnicity, gender identity, sexual orientation, religion or national origin; (iv)  Members of one (1) race, one (1) sex, one (1) color, one (1) ethnicity, certain gender identity, sexual orientation, religion or national origin cannot and should not attempt to treat others without respect to race, color, ethnicity or sex, gender identity, sexual orientation, religion or national origin; (v)  An individual’s moral character is necessarily determined by his or her race, color, ethnicity, sex, gender identity, sexual orientation, religion or national origin; (vi)  An individual, by virtue of his or her race, color, ethnicity, sex, gender identity, sexual orientation, religion or national origin, bears responsibility for actions committed in the past by other members of any class listed herein; (vii)  An individual should feel discomfort, guilt, anguish or any other form of psychological distress on account of his or her race, color, ethnicity, sex, gender identity, sexual orientation, gender identity, religion or national origin; or (viii) Meritocracy or traits such as a hard work ethic are racist or sexist, or were created by a particular class to oppress another class.”
• “No public school or public postsecondary educational institution shall: (a)  Require, request, or consider diversity statements or similar materials from job applicants as part of the hiring process, contract renewal process, evaluation or promotion process; (b)  Require, request, or consider diversity statements or similar materials from applicants for admission to academic programs; (c)  Require, induce or compel students or employees to participate in diversity training; (d)  Require, induce, or compel students or employees to endorse, assent to or publicly express a divisive concept; (e)  Penalize or discriminate against a student, employee or contractor on the basis of his or her refusal to support, believe, endorse, embrace, confess, act upon or otherwise assent to a divisive concept; or (f)  Maintain any programs, including academic programs or courses, or offices that promote or endorse divisive concepts or concepts promoting transgender ideology, gender-neutral pronouns, heteronormativity, gender theory, sexual privilege or any related formulation of these concepts.”
• “All public schools and public postsecondary educational institutions in Mississippi, shall teach, promote and distribute information based on the scientific policy that there are two (2) genders, male and female.  A male has a chromosome of XY, and a female has a chromosome of XX.”

Notwithstanding the plaintiffs’ obvious mischaracterizations of HB 1193, Judge Wingate — on July 20, 2025 — issued a short-term Temporary Restraining Order (TRO) as an emergency measure to block enforcement of the bill for a strictly limited time period of 28 days (expiring August 17, 2025).

After Wingate entered the TRO blocking HB 1193 from taking effect, both sides of the legal debate noticed significant factual errors in the text of his ruling – e.g., references to plaintiffs and defendants that were not parties to the case, and quotations that had not been spoken or written by anyone involved in the case. In  a FindLaw.com article, attorney Vaidehi Mehta enumerated with specificity a number of those errors. Some notable excerpts from her piece:

• “You don’t have to read very far into Judge Wingate’s order to smell something off. In its very first footnote, the document listed an array of plaintiffs, including the Mississippi Library Association and Delta Sigma Theta Sorority Inc.  The problem? None of these organizations had ever been parties to the lawsuit. The order also named officials such as the ‘Commissioner of Higher Education’ and ‘State Superintendent of Education’ as defendants, even though neither had been sued in those capacities.”
• “The order repeatedly referenced terms such as ‘race or sex stereotyping,’ ‘race or sex scapegoating,’ and ‘critical race theory,’ placing these phrases in quotation marks as if they were direct quotes from HB 1193. This created the impression that these specific concepts were expressly defined or prohibited by the statute. However … none of these phrases appear anywhere in the law itself.”
• “Judge Wingate’s order referenced the ‘cessation of DEI offices and initiatives at Jackson State University, Alcorn State University, and Hinds Community College’ and ‘cancellation of implicit bias and Safe Zone training.’ It cited the plaintiff’s complaint as the source of these allegations. The problem … is that the plaintiffs never made any such allegations.”
• “One of the more puzzling aspects of Judge Wingate’s original temporary restraining order was his reference to a case called ‘Cousins v. School Board of City of Norfolk,’ supposedly decided by the Fourth Circuit in 1974. When attorneys involved in the litigation searched legal databases for Cousins v. School Board of City of Norfolk from 1974, nothing turned up — not even a remotely similar case with that citation or party configuration…. [T]he case simply did not exist in the record of published federal appellate decisions.”
• “Perhaps the most egregious error was the use of supposed evidence that simply wasn’t there. The order cited sworn declarations from four individuals (Brandy Williams, Leslie-Burl McLemore, Dr. Rhea Bishop, and Natalie Collier) as key support for the court’s findings. It even pointed to specific exhibit numbers in the case record … as if these documents were filed and available for review. But when attorneys and observers checked the actual court filings, they discovered a different reality. The exhibits that Judge Wingate referenced did exist, but they contained declarations from entirely different people.”

In light of the foregoing errors, the Mississippi Attorney General’s office joined with the plaintiffs in filing a motion on July 22, 2025, to clarify or correct the judge’s order.

In response, Wingate rescinded his July 20 TRO and replaced it with a corrected version on July 23. He then removed the initial TRO from the public docket, backdating the amended order to July 20, to make it look as though the corrected version were the original.

After Wingate replaced the original ruling with a corrected version, lawyers for the state of Mississippi asked him not only to explain why there had been so many errors in the original, but also to “preserve the record” of where the errors had occurred and subsequently had been corrected.

But Wingate complied only partially. In early August 2025 he said that his original ruling contained “clerical errors referencing improper parties and factual allegations,” but he declined to explain why or how they had found their way into his TRO. “No further explanation is warranted,” wrote the judge, refusing also to make the original, error-filled ruling accessible on the public docket.

On August 18, 2025, Wingate upgraded his July 23 TRO to a Preliminary Injunction mandating the continuance of a statewide prohibition against the enforcement of HB 1193 for however long the lawsuit might go on. “This Court generally agrees with Plaintiffs’ view of the challenged portions of (House Bill 1193),” he wrote. “It [the statute] is unconstitutionally vague, fails to treat speech in a viewpoint-neutral manner, and carries with it serious risks of terrible consequences with respect to the chilling of expression and academic freedom.”

Asserting further that HB 1193 was “at odds” with “the public interest of this State,” the judge added: “Although Defendants wish this Court to narrow its gaze to the roles of affected persons—whether the speech is public versus private—this Court has delved deeper and looked at the contours of speech prohibition, causing this Court to visit the concept of academic freedom.”

On October 6, 2025, U.S. Senate Judiciary Committee Chairman Chuck Grassley wrote a letter to Wingate, asking about his alleged use of generative Artificial Intelligence (AI) to draft court orders with little to no verification of their accuracy by human analysts.

In response to Grassley’s letter, Wingate on October 21 sent a letter to Robert Conrad, Director of the Administrative Office of the Courts, stating that one of his law clerks had used an AI tool known as Perplexity “strictly as a foundational drafting assistant to synthesize publicly available information on the docket.” “The law clerk who used GenAI in this case did not input any sealed, privileged, confidential, or otherwise non-public case information,” Wingate wrote. “The standard practice in my chambers is for every draft opinion to undergo several levels of review before becoming final and being docketed, including the use of cite checking tools. In this case, however, the opinion that was docketed on July 20, 2025, was an early draft that had not gone through the standard review process. It was a draft that should have never been docketed. This was a mistake.”

“The root cause of the errors identified in Defendant’s unopposed motion to clarify/correct was a lapse in human oversight, specifically the posting of a draft opinion instead of a final one and the failure to put the draft opinion through the final review process,” Wingate continued, adding: “Consistent with the Code of Conduct for United States Judges, I have taken appropriate action to address the law clerk’s conduct that resulted in the mistake. Additionally, I immediately implemented corrective measures in my chambers, including a plan whereby all draft opinions, orders, and memorandum decisions undergo a mandatory, independent review by a second law clerk before submission to me. All cited cases are printed from Westlaw and attached to a final draft.”

Condemnations of Wingate’s Lack of Professionalism

Indiana University law school professor Charles Geyh described Wingate’s original mistakes as “more egregious than I’m accustomed to seeing in federal court.”

“Our attorneys have never seen anything like this,” said an official from the Mississippi Attorney General’s Office.

Stephen Gillers, a professor at New York University School of Law, said that judges are ultimately accountable for the accuracy of their rulings, regardless of whether they are drafted with AI or traditional research. “The judge has to read the case which they cite,” Gillers stated. “If the judge is citing a case, whether the case comes from AI or a clerk doing traditional research, the judge should read that case.”

Footnotes:

[1]  https://ballotpedia.org/Henry_Wingate

[2]  Mike Gonzalez, Senior Research Fellow at the Heritage Foundation, has defined DEI as follows:

“DEI mushroomed under the Biden Administration,… which directed federal agencies to embed ‘equity’ as a central principle of governance…^. In practice, DEI transformed the federal government’s role from enforcing nondiscrimination law to actively doing the opposite—pursuing color-conscious policies—in order to manage demographic outcomes across society….

“Diversity demands that government, the private sector, the universities, all societal entities … choose individuals because of their membership in the immutable characteristics of race, sex, etc., regardless of merit, talent or virtue, until an office, a classroom, a military base, etc. resembles a given base population statistically. It constitutes an affront to the dignity of the individual….

“But notice that people would not be chosen—hired, promoted, elevated, etc.—according to diversity of opinion, on the contrary. The goal is groupthink; ending up with people mouthing off the same orthodoxy….

“The traditional meaning and sound of the word ‘equity’ are so close to the old American promise of ‘equality’ that many Americans may still believe it to mean that. That the word now means its functional opposite…. No matter how much harder you have exerted yourself than the person sitting next to you, you both should end up getting the same amount. That, I put to you, is not the American expectation, it is the Marxist promise, one written in sand, of course….

“Inclusion [means] an enforced separation of people by race…. [It] means including only expressions that promote the reigning orthodoxy and including those that dissent. Inclusion, in this understanding, means exclusion.

“All of this represents a significant departure from the traditional civil rights framework. The Civil Rights Act of 1964 and the Equal Protection Clause of the Constitution’s 14th amendment are grounded in the principle that government must treat individuals equally under neutral law, without regard to race or other immutable characteristics. DEI frameworks, by contrast, increasingly define fairness in terms of statistical parity among groups. DEI is therefore illegal and un-American…. But DEI is also immoral, as it proposes to treat people differently because of membership in an immutable characteristic, that is, a trait they were born into and which they can never change, such as race, sex, national origin, etc.”