‘You messed with the wrong guy’: Florida Man menaces teen with a gun over ding-dong ditch

A Florida man, Santiago Cairo, of Boca Raton, has been arrested and charged with aggravated assault with a deadly weapon. He allegedly pulled a gun on a 14-year-old kid playing the classic, and sometimes infuriating, prank known as ding-dong ditch. Cairo, 40, was reportedly so incensed by the doorbell ring-and-run that he armed himself and confronted the teen, yelling, “You messed with the wrong guy,” which is, quite frankly, a line straight out of a movie.

The incident went down around 8 PM on October 16, 2025, at Cairo’s house, according to Fox. Cairo noticed a group of people near his front door and immediately thought they were trying to break into his home. To be fair, with the way property crime is going these days, it’s easy to get jumpy, but this time around, the motivation was mischief, not robbery. Cairo called 911, which is the right thing to do, but then he decided to take matters into his own hands, arming himself with a gun before deputies could even arrive.

This is where the stories start to feel like night and day. Cairo’s account to the authorities paints one picture. He told investigators that he absolutely did not aim the gun at the teenager. Instead, he claimed he kept it in a “low ready position” while waiting for the police. That sounds like a guy who’s trying to de-escalate, or at least maintain a defensive posture without being overly aggressive.

This ding-dong ditch turned into an armed threat

On the other hand, the young prankster’s account is much scarier. The teen admitted to the ding-dong ditch but alleged that Cairo confronted him, holding both a flashlight and a gun. Along with the “You messed with the wrong guy” line, the teen said Cairo ordered him to get down on his knees and even grabbed his shoulder in an attempt to push him to the ground. That’s a massive difference from a “low ready position,” and it’s no wonder the kid ran straight to the arriving law enforcement officers for safety when they finally showed up.

The police investigation quickly determined that the juvenile never attempted to break in; it really was just a silly prank. Moving forward from that discovery, deputies booked Cairo on the serious charge of aggravated assault with a firearm. He was eventually released from the Palm Beach County Jail after posting a $10,000 bond.

Even Cairo himself reportedly admitted to police that he “went too far” when he was responding to the situation, which, I mean, is a pretty massive understatement given that a firearm was involved. His attorney, however, has maintained his client’s innocence, stating that Cairo “never in fact pointed his firearm at anyone or put his hands on anyone.” Still, the court will have to decide whether the teen’s fear was reasonable given the commands and the presence of a weapon.

While you have a right to protect yourself and your property, self-defense and Stand Your Ground laws definitely have their limits. What makes this story even more interesting is the strong support Cairo is getting from his neighbors.

Mary Elizabeth Hall, who lives right next door, has publicly defended him and even expressed her disappointment at the outcome. She told reporters that she “question[s] if it was a prank, or if they were trying to steal something,” adding that their South Florida neighborhood has been hit with an influx of car break-ins. This gives you a little more context as to why Cairo might have been so quick to assume the worst.

Hall believes her neighbor did the right thing in trying to protect his home and property, going so far as to say, “My neighbor did the right thing, and the outcome was not the right thing.” She’s hoping for a better result for him in court next month. This sounds silly, as others have lost their lives to people reacting poorly to this small prank. She added, “I hope the outcome is that the young man learns a very serious lesson, and that my neighbor, Santiago, his name is cleared.”