A Florida woman was initially booked on charges of disorderly conduct, trespassing, and resisting an officer, according to Guessing Headlights. As she got in trouble for trespassing, the historical records from the Monroe County Sheriff’s Office showed that the woman entered a no-contest plea to trespassing and resisting detention. The bodycam footage of the incident was also uploaded to YouTube by Police Insider.
A judge found her guilty of both misdemeanor offenses, while prosecutors dropped the separate charge of hindering or interfering with police. She then got 12 months of probation, and later, a probation officer reported that she had tested positive for alcohol, violating a special condition of her probation.
Judge Mark Wilson signed a warrant related to the alleged violation, after which she was taken into custody. A few days later, she admitted to violating her probation. The judge revoked her probation and sentenced her to 13 days in the Monroe County Jail, giving her credit for the 13 days she had already served.
It all started with something very small
Police had been called to deal with a disturbance involving a group of customers near the swimming pool at Dante’s Pool Bar and Restaurant. The officer initially instructed the group to collect their belongings, pay their tab, and leave the property. “You have two minutes to get ready,” he said. “If you’re not done, I’m taking you to jail for trespassing.”
One woman wearing a blue plaid swimsuit was preparing to leave when her boyfriend picked her up and tried to carry her toward the exit gate. The officer was okay with the scene as the man was helping the woman, who was reportedly drunk according to the boyfriend, get off the property. However, the situation changed when she demanded to be put down.
That is when the officer stepped in and moved to handcuff the woman. “What am I going to jail for?” she asked. “I gave you two minutes to get your stuff and leave, but you wouldn’t,” the officer replied.
The woman kept insisting that she did nothing wrong, but the officer explained that she should have let her boyfriend help when he was trying to get her away from the situation. Instead, she told him to step away and apparently tried to start a fight with her boyfriend.
As she was placed inside the police vehicle, the boyfriend came to understand what went wrong. He explained that he had been closing out the group’s tab and wished he had intervened sooner.
The officer told the boyfriend that he did the right thing. However, he added that continuing to physically restrain someone who wants to be let go could have potentially exposed him to allegations of battery or kidnapping, and he could have gone to jail for that. The officer also revealed that the man whose behavior led to the original complaint had already left peacefully.
The boyfriend also mentioned that the bar was reportedly not pressing charges, so he failed to understand the process behind his girlfriend’s arrest. It was for trespassing, and because it looked like the woman was about to get physical with the boyfriend, the officer explained.
Published: Oct 15, 2026 03:30 pm