It was the day after the senior pranks when a Kendall County teenager and his friends were laughing about the annual tradition in their English class.
That year, all in good fun, Jackson Leggett said some of the seniors at Newark Community High School had toilet-papered the principal’s house and parked speed boats at the school.
They also chatted about a rumor going around about potential vandalism at the school, which Leggett said he tried to quash with the sarcastic quip, “What do you think I’m gonna do? Burn the school down?”
This October 2024 conversation — which Leggett intended as a joke — completely upended his senior year, according to a lawsuit Leggett filed last month in federal court against the school district, the superintendent, his teacher, Kendall County and a sheriff’s deputy.
The suit alleges that the then 17-year-old was wrongfully arrested, falsely charged with felony disorderly conduct and forced to miss out on many senior year milestones over what should have been treated as a “minor school disciplinary issue” at most.
The now 19-year-old also told the Tribune he was left “constantly nervous and scared” for months, and that his reputation was damaged in the small town, located about an hour and a half drive from Chicago. He said he’d never been in trouble with the law before.
“Even in schools, students have First Amendment rights,” said Julia Rickert, Leggett’s attorney and a partner at Loevy & Loevy. “They’re limited in that the school can punish speech sometimes, in a way that in public they couldn’t, but that they can’t make it into a crime.”
Tim Ulrich, the superintendent and principal at Newark Community High School District 18, said in a statement that the claims raised against the district and its employees are “meritless” and that the district “intends to vigorously defend itself and its employees against these claims.”
Dan Briars, a spokesperson for the Kendall County sheriff’s office, also said the department can’t comment on specific details of pending litigation but that they conduct “thorough, comprehensive investigations, and any resulting charges or arrests are based on and supported by probable cause.”
Senior pranks
Senior pranks had long been a rite of passage at Newark, Leggett said. He heard about them happening during homecoming week when he was a freshman, and from his brother who’s two years older than him.
The pranks the students chose in 2024 — toilet-papering the principal’s house and school and parking the boats — didn’t seem “out of the ordinary” to Leggett.
In fact, the lawsuit alleges that Ulrich was present for the pranks and told students they could continue so long as they “did no permanent damage.”
“I’m not going to say (Ulrich) was happy about it obviously because nobody wants that to happen to the school,” Leggett said. “But it happens every year, and he gave us permission. He could have said no.”
Another popular rite of passage in the Chicago area called “senior assassin” has grabbed headlines in recent months. A high school student in northwest Indiana is also facing a felony charge after participating in the game, which police warned can be dangerous.
But Leggett didn’t get in trouble for the pranks themselves, the lawsuit said, rather the jokes he made just hours after in class.
The teacher reported the morning’s conversation to administrators, according to the suit. On a discipline referral form, she wrote that Leggett had made “bizarre and unbelievable comments” such as burning down the school.
She also referenced alleged comments that Leggett denies making, such as burning Ulrich’s house and stealing his wife. She acknowledged in this form, however, that Leggett had been “making jokes.”
An assistant principal suspended Leggett for three days, and although he believed the punishment was unfair, he thought the ordeal was over. But the suit alleged that the principal “was determined to see it become a criminal matter,” and that he contacted the school resource officer, a Kendall County sheriff’s deputy.
During an interview with the deputy, the teacher said she told Leggett and another student to stop talking about the pranks and that “I wouldn’t be laughing and goofing off about it because (administrators) are gonna talk to you,” body camera footage shows.
She overheard the duo saying they maybe needed to “take it to the next level” because they didn’t understand what they could possibly be punished for, according to the footage.
“I feel like we sometimes are very lenient with them where other schools would not be so lenient with them,” she told the deputy, later adding, “Whether they were joking or not you never know sometimes.”
At the end of the interview, the deputy said although Ulrich was considering legal action, “I don’t think I may have a lot to go on just based off what you said … If it came off in a joking manner.”
The deputy wrote in a report that Ulrich, who wasn’t in the classroom at the time, “did not perceive the comments as a joke” and that he felt threatened by them.
Leggett said he’s completely baffled about why the principal allegedly pushed to escalate the case.
“I have no idea,” he said. “That’s what I want to figure out with this lawsuit.”
‘Huge piece taken out of my life’
Leggett didn’t think anything of the two police vehicles that pulled up near him while he was mowing a client’s lawn, at least at first. At the time, he ran a landscaping business with a friend.
He was shocked when officers walked up and arrested him. Leggett remembers asking if he could load up his mower and drive down the road so he wouldn’t be arrested at a client’s house, a request they denied.
“I was just very scared and worried and pretty mad,” he said. “I’ve never been arrested before. I have no idea what any of that looks like.”
He was charged with felony disorderly conduct and detained for eight days at a juvenile facility in Kane County. The charge was eventually dropped about seven months later in May 2025, according to the lawsuit. But Leggett said he can’t so easily forget his time at the detention facility.
“It was the absolute worst thing I’ll ever experience. It’s tough to talk about,” he said. “I had no idea when I was gonna get out of there. There’s hardly any windows. I couldn’t have any sunlight. I was going crazy in there.
“It’s something I’ll never forget, and I want to forget it,” he added.
While living with the threat of prosecution over his head, the suit alleged, Leggett’s education also suffered. He had to take classes online only for the rest of the year. He couldn’t attend senior prom or walk at his high school graduation. He even was excluded from the yearbook, the suit noted.
Leggett also couldn’t play basketball, a sport he said he’d enjoyed ever since he could dribble.
“It made me pretty sad because watching all my friends be able to do everything when I’m sitting at home,” he said.
One of the toughest parts of the situation, Leggett said, was the judgment he faced from others. While his friends “knew the truth,” he said it felt like others would talk behind his back, even when he went to the gas station. The landscaping business also took a massive hit, he said.
Leggett said his favorite pastime is hunting, something he’s no longer able to do. Because the sheriff’s deputy flagged him as a “clear and present danger” to state authorities, the suit alleged he’s been unable to obtain a firearm owner’s identification card, a violation of his Second Amendment rights.
“It’s a huge piece taken out of my life,” he said. “I just love being out in nature. It’s almost therapeutic, you know, like sitting up in a tree, waiting on a deer out in the woods, it’s beautiful.”
Leggett, who now works as a machine operator, said he hopes by sharing his story publicly that his friends and neighbors can get a better understanding of what happened to him. He said he also wants answers from the school and police.
“I think people are starting to change their ideas about me,” he said. “I hope this doesn’t happen to anybody else and that other schools see this and take things more seriously instead of just arresting people.”
