Regan Killackey was goofing around with his son and daughter in a party supply store in September 2019, snapping photos. His daughter put on a mask of Donald Trump. His son held up a silver plastic sword, and Killackey grimaced.
Killackey, a high school teacher, posted the family photos to his personal Instagram.
Five years later, in the days following the attempted assassination of Trump at a campaign rally, an anonymous tipster sent a screenshot of the Trump mask photo to the Oklahoma Department of Education with a description: “Posted picture on personal Instagram account of the fictitious stabbing of fake presidential candidate mask.”
The department took swift action, and filed to take away Killackey’s teacher certification — the harshest discipline the department can take against an educator. The proceedings are typically reserved for serious offenses, such as child abuse, predatory behavior or criminal charges.
But in Killackey’s case, Superintendent of Public Instruction Ryan Walters prioritized punishing a teacher over political speech he disagreed with in order to score political points.
The First Amendment prohibits disciplining a teacher for political speech made as a private citizen, multiple lawyers and free speech experts said.
“For Walters, who is attempting to build this profile of a patriotic American wrapped in a flag, this sort of behavior is about as un-American as it gets,” said Ryan Kiesel, a civil rights attorney and former state representative.
This shift began with Summer Boismier, who taught English at Norman High School and caught Ryan Walters’ attention in 2022 with a demonstration against House Bill 1775, a state law prohibiting certain conversations about race and gender.
Prior to the start of school that year, Boismier covered her bookshelves with red paper, the words “books the state doesn’t want you to read,” and a QR code to the Brooklyn Public Library, which offers any student free access to banned books.
Walters, then secretary of education, called for the board to revoke her license.
“There is no place for a teacher with a liberal political agenda in the classroom,” he said.
As superintendent, he continued to pursue revocation, even though she resigned and moved out of state. Walters and the board rejected a hearing officer’s recommendation that Boismier keep her teaching license and, even though her certification expired this summer, voted in August to revoke it.
Walters has said Boismier violated the teacher’s code of conduct.
The department did not make Boismier’s revocation order public until a federal judge ordered SDE to explain whether the board violated an injunction that postponed enforcement of parts of House Bill 1775. In the response filed Sept. 12, the Department of Education said Boismier’s certificate was revoked because she violated three conduct rules requiring teachers to meet certain professional performance and conduct standards and to “protect the student from conditions harmful to learning or to health and safety.”
Sending a Message
For Killackey, a 20-year veteran educator, the department has taken first steps in the process to remove his license but he remains certified.
He teaches AP English at Edmond Public Schools. He’s one of the plaintiffs suing the state over HB 1775 because, he said, the law inhibits his ability to teach. After the law passed in 2021, Killackey said school officials advised teachers to avoid books by non-white and female authors. He said he wants his class to read books such as To Kill a Mockingbird and Their Eyes Were Watching God, so Black students see themselves reflected in the course material, too.
Limited details about the allegations against Killackey were gathered from the anonymous complaint to the department, obtained under the Oklahoma Open Records Act, and public statements by Walters, who taught high school history before his foray into politics.
“We want to make sure to send a message loud and clear: no one will be able to teach in the state of Oklahoma if they advocate for the assassination of President Trump, or any elected official,” Walters said, referring to Killackey and another teacher without naming them at the July 31 meeting.
He posted the soundbite to X and tagged Libs of TikTok, its founder Chaya Raichik, and former president Donald Trump.
The tip about Killackey came two weeks earlier from an IP address that Oklahoma Watch traced to New York City’s city hall. The tipster listed their name as Concerned Citizen.
“I am a tax pay (sic) and will NOT condone this type of indoctrination of our youth,” they wrote. “Please look into this matter.”
The department is also trying to take away Ardmore teacher Alison Scott’s certification over a social media post. Two weeks earlier, Libs of TikTok, whose posts on X fuel outrage, division, and have been connected to bomb threats, amplified Scott’s reply to a Facebook post after the attempted assassination of Trump.
“Wish they had a better scope,” reads the comment, followed by the shrug emoji.
Walters responded on X right away.
“This is unacceptable,” Walters wrote. “SDE is investigating. We will not allow teachers to cheer on violence against @realDonaldTrump.”
Later the same day, Walters, in another X post, wrote he’d be “taking her teaching certificate.”
In comparison, the department waited more than a year to file to revoke the teaching certificate of Phil Koons, a football coach accused of bullying and harassing student athletes. Parents voiced concerns at a Ringling school board meeting in February 2023. Koons was placed on administrative leave while law enforcement investigated, but that summer, the superintendent reinstated Koons, KFOR reported.
Prosecutors charged Koons with outraging public decency, a misdemeanor, in October, and that’s when he stepped away from the school district, according to The Oklahoman. (Koons, in federal court documents, denied the allegations.)
Hidden Allegations
The Department of Education has delayed multiple requests by Oklahoma Watch for a copy of their application to revoke Killackey’s certificate, which includes a summary of the allegations and a statement of facts. A request made Aug. 6 under the Oklahoma Open Records Act is pending.
Cara Nicklas, an attorney who represents the Board of Education, said in a voicemail message that it’s up to the department to decide whether to release the document.
“My initial concern is that we can’t release applications because that’s in the investigatory process,” she said. “That would be because of a need to protect the teachers from unfair publicity when there hasn’t been any conclusion made about the allegations.”
The department has previously provided such documents to Oklahoma Watch under the law, which states agencies can’t deny access to records that are otherwise public just because the records have been placed in an investigation file.
In August, the department amended its complaint against Killackey by adding a video clip its investigator found online. In the video, posted in 2021, Killackey heckles a street vendor in Edmond selling Trump merchandise, asking through the window whether he has any Al-Qaeda or Taliban hats.
In response to questions about Killackey and Scott, Director of Communications Dan Isett said: “Just like in many other professions, Oklahoma teachers are bound by professional conduct standards which set a high bar for teachers’ behavior both in and out of the classroom.”
Courts, though, have upheld public employees’ constitutional right to free speech, with few exceptions. Political speech is central to the First Amendment protection.
“It doesn’t matter if people find the remarks unpalatable,” said Ken Paulson, director of the Free Speech Center at Middle Tennessee State University. “No amount of political outrage can undermine their constitutional rights.”
One exception is when the comments are an extension of their job, but the state would have to show the teachers’ comments made as part of their professional duties, not as private citizens, Paulson said.
That didn’t stop Libs of TikTok from trying to get workers fired for comments made in the wake of the Trump shooting. They included school and university employees, a restaurant worker, a fire chief and a pharmacy worker. The account’s founder, Chaya Raichik, has endorsed Trump for president.
Libs of TikTok’s involvement could bolster the public workers’ defense, showing the complaints were political and not a question of professional competence, Paulson said.
Another exception to free speech is if comments incite violence, but it’s narrow, said Aaron Terr, director of public advocacy at the Foundation for Individual Rights and Expression. He considered Scott’s comment and Killackey’s post and said neither sounded like incitement or true threats, a standard established by a 1969 Supreme Court decision that overturned the conviction of a Ku Klux Klan leader for his speech at a rally.
The courts again upheld free speech rights in the 1980s case of a Houston woman fired from her job at a constable’s office. On the day President Ronald Reagan was shot and wounded, she was heard on the phone saying, “If they go for him again, I hope they get him.”
After a judge reinstated her with back pay, the woman said she meant she didn’t like Reagan’s policies, not that she was going to shoot him herself, according to a 1988 story in the Los Angeles Times.
Due Process Disregarded
Killackey found out the state was seeking revocation when his name appeared on the July 31 board agenda. The Department didn’t mail its application to revoke until Aug. 22, weeks past the statutory deadline of three days.
Revocation is a legal process and the teacher holds the right to have a hearing, bring witnesses and obtain legal representation. At its core is due process and the right to know the nature of the charges and evidence.
Due process rights exist to protect citizens from unfair or improper government intrusion.
Teacher certification, which requires a bachelor’s degree in education, passing scores on two competency exams, is — legally — a property right, said Brent Rowland, an attorney at the Oklahoma Appleseed Center for Law and Justice in Tulsa. That’s why there are rules and processes limiting when certification can be revoked.
“If you think about the investment this represents for a teacher, not only education, training and, in a lot of cases, years of service, there have to be protections around an administrative agency or any government action wiping those out,” Rowland said.
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Oklahoma Watch, at oklahomawatch.org, is a nonprofit, nonpartisan news organization that covers public-policy issues facing the state.