Senior Prank at WHS Turns Destructive, Triggers Investigation by School Administrators and Police

A late-night break-in that school officials describe as an organized “senior prank” drew an estimated 100 students into Wilton High School this week, leaving behind widespread vandalism and prompting a joint investigation by administrators and the Wilton Police Department.

Principal Robert O’Donnell told GOOD Morning Wilton that the incident escalated well beyond traditional end-of-year hijinks, causing costly damage and significant disruption to the school community.

The incident involved approximately 100 students who entered the building in two separate waves — first around 10:30 p.m. on Wednesday, May 14, and again around 1:30 a.m. on Thursday, May 15. O’Donnell called it a “pre-planned, coordinated effort” that resulted in extensive vandalism.

Administrators spent Thursday conducting what O’Donnell called “the initial investigatory phase,” interviewing students and reviewing surveillance video to try to determine a timeline, and who was involved and to what degree. Based on what they’ve seen so far, O’Donnell said whatever the original intent was, it’s apparent things quickly escalated.

“Once they get in with a lot of kids, things can quickly go south, and in spite of what intentions they may have had, they ended up doing things they really should not be doing,” he said.

Today (Friday, May 16) is the last day of in-school attendance for seniors. They typically spend the last few weeks of the school year before graduation on individualized projects. In anticipation of end-of-year pranks that are likely to occur during seniors’ final week of classes, school leaders had tried to avert such an incident by ensuring doors were locked and increasing police patrols.

Senior pranks have been a tradition, but graduating classes typically consult with administrators before executing a prank that’s usually more benign.

“We’ve got a long history of trying to work on something that the kids find… interesting, challenging, something localized, where they feel like they’ve done something,” O’Donnell said.

“The class government officers that we were working with were not aware of the whole scope of this, so… there’s no indication right now that they were complicit. But you can get other groups that go more rogue, and that’s certainly part of what happened here,” he said.

At WHS since 2004, O’Donnell said he’s never seen something like what happened this year. “This is on the more extreme end,” he said.

The students’ actions included:

• Graffiti and vandalism using grease pens to write inappropriate and what O’Donnell called “unsavory” messages on dozens of windows and other surfaces
• Rearranging cafeteria furniture, including stacking all the chairs
• Displacing significant pieces of athletic equipment
• Smearing food on walls and doors
• Moving one golf cart from the garage into the cafeteria, and driving the other around inside the building
• Placing an abandoned, spray-painted pickup truck directly in front of the school’s main entrance

O’Donnell sent a letter to senior families and students Thursday morning to address what had happened.

“Seniors, I write to you to send the clear message that this incident went too far.  Parents, I write to you to ask that you ensure that your students are supervised and accounted for in the coming nights,” he wrote.

The cleanup effort has been substantial, with custodial staff working tirelessly to restore the school to its normal condition.

“The amount of time it takes to clean even one large window with a bunch of grease pen marked on it is one thing… we didn’t count them, but let’s say there’s 50 of them. Well, that’s a lot of time to clean things up,” he said.

“You get a bunch of kids inside of school with equipment and markers and some food stuff, and it just becomes a complete mess. That all is disruptive. It takes time to get it back in place before we could have kids in there in the morning before school,” O’Donnell said, adding, “I feel for our custodial staff.”

The school is working closely with the Wilton Police Department, with School Resource Officer Christopher Ventura leading the investigative process on behalf of the WPD. Police Information Officer Lt. Anna Tornello told GMW that while the police blotter listed the incident as “criminal mischief,” the report is not yet available as it has not been completed.

When asked whether any charges — trespassing, breaking and entering, vandalism or destruction of property — were being considered, she said that no criminal charges have been filed and “no arrests will be made at this time.”

“The actions stemmed from a ‘senior prank’ by the senior class, leading to their last day of school,” Tornello wrote, adding that disciplinary action will be “taken by the Wilton Schools administration.”

O’Donnell said the investigation is still open and the school’s primary focus remains on understanding the full scope of the incident before determining appropriate disciplinary actions.

Discipline will follow district policies, though specific penalties have not been decided, and O’Donnell indicated that “anything is on the table,” including potential restrictions on graduation participation, prom attendance, and other senior year privileges for those directly involved.

While disappointed, WHS administrators are being careful not to condemn the entire senior class. O’Donnell said most seniors had no role in the prank and still have positive milestones ahead.

“We have a lot of really, really good kids in this town. We don’t want to paint an entire class with a broad brush,” O’Donnell emphasized, adding, “They do have a lot to look forward to, and you just don’t want to see it tarnished … by stuff like this.”

GOOD Morning Wilton will continue to update this story once Wilton Police provide more information or school officials make any updates.

Editor’s note: The story has been updated to add two sentences that were originally omitted due to an editing error. The sentences were quotes from Lt. Anna Tornello in response to questions about possible charges or arrests being made in the case.