The Price of Arrogance: A Young Man’s Wake-Up Call

For over 40 years, I’ve sat on this bench, watching people, some good, some not, come before me. I’ve witnessed fear, anger, pride, and even humility. One thing I’ve learned is simple: court is not just about punishment, it’s about truth and respect. It’s where people come to learn lessons they might not have heard before, especially the lessons their parents forgot to teach them.

On a rainy Tuesday, October 14th, a case landed on my desk that I knew was going to be trouble. Case number 24 CR7719. The charges? Disorderly conduct, harassment, criminal mischief, and most disturbing of all, assault on a public-facing employee. The defendant’s name was Carter Winslow, 22. Even his name sounded expensive, like something you’d hear in an exclusive club.

When Carter walked in, the room grew quiet in that particular way—people didn’t notice him for his danger, but because he looked out of place, like the kind of person who doesn’t belong among the rest of us. He was dressed to impress—white Dior button-down, LV belt buckle, Christian Louboutin shoes with the signature red soles, a big Rolex on his wrist, and a smirk on his face like the courtroom was his stage.

His lawyer, Daniel Crest, stood confidently by his side, and the two seemed like they were already preparing to leave. Across from them, the victim, Luis Rivera, sat calmly. A 56-year-old janitor and Desert Storm veteran, Luis didn’t have the arrogance Carter wore like a badge. His hands were rough, his clothes plain, but his posture said everything—he had dignity. He was a man who worked for everything he had, and he carried the weight of his past, including raising his granddaughter, Sophia, whose mother struggled with addiction.

The incident happened on September 27th at 10:47 p.m., just one minute before the case was filed. Carter had been partying with friends at a rooftop lounge when they came into the Harbor Tower lobby, loud and disruptive. Luis, just doing his job, politely asked them to lower their voices. That’s when Carter decided to turn it into a game. He taunted Luis with cruel words, mocking his job, his life, and then shoved his cleaning cart, knocking it into the wall.

But it didn’t stop there. As Luis bent down to pick it up, Carter slapped the caution sign out of his hands and laughed. “Careful, he might slip on his own poverty.” That moment wasn’t just about a cart getting shoved. It was about someone who thought their wealth gave them the right to humiliate another human being.

I asked Luis why he didn’t walk away, and his response stuck with me. “Because I need this job,” he said simply. That hit hard. Luis wasn’t working because he wanted to; he was working because he had no choice. His wife had passed away four years ago from breast cancer, and now he took care of his granddaughter, Sophia, whose asthma cost him over $300 a month in inhalers. Every shift, every dollar, was for her.

When Officer Megan Halley testified, she told the court that after the incident, Carter was found standing by his black Lamborghini Urus, smugly telling officers, “I pay more in taxes than this whole building makes.” His arrogance seemed endless. But the facts kept coming. Security footage showed Carter shoving the cart, laughing, and mocking Luis. But then it got worse. A Snapchat video surfaced. Carter’s friend had filmed the entire incident, and the caption read: “Watch the help scramble,” followed by Carter’s voice laughing, “Say thank you, Luis. Say thank you for my generosity.”

The video shocked everyone. It wasn’t just a joke anymore—it was pure cruelty. Luis had been reduced to an object for Carter’s amusement, all while he filmed it for the internet to see. Carter tried to brush it off, saying, “It’s just the internet. People post stuff.”

But what he didn’t realize was that it wasn’t just the internet. It was a courtroom, and there were consequences. And then, like a storm brewing, a witness stepped forward—Rachel Kim, a nurse at Rhode Island Hospital, who had witnessed the entire thing. She said she had seen a lot of suffering in her life, but never had she seen someone enjoy causing pain the way Carter had.

Carter’s defense was that he was drunk, that it was all just a misunderstanding. He offered an apology and suggested anger management classes, hoping for a dismissal. But when he scoffed and mocked the court, something inside me shifted. He didn’t get it. He wasn’t sorry for what he had done. He was sorry he had been caught.

And then came the turning point. Officer Halley brought up a detail that changed everything. After Carter had been released that night, he had posted a picture of himself with a bottle of champagne, showing off his expensive watch and mocking the incident with the caption, “Just got arrested because a janitor cried, ‘Poverty is loud.’”

But what Carter didn’t realize was that he had just handed the authorities a gift. The photo tagged the location—Harbor Tower, the exact building where there had been a string of break-ins. The FBI had been investigating these thefts, and Carter’s post gave them the key they needed. Carter had just incriminated himself with his own words.

I turned to Carter, “You came into my courtroom thinking this was entertainment. You mocked a man who served his country and cleaned up after people who thought they were better than him. You filmed it. You posted it. You laughed.”

Then I asked, “Where do you work, Mr. Winslow?”

He smugly replied, “I don’t work. My family has investments.”

I could see the disparity now—he wasn’t just a spoiled kid. He was someone who thought his money gave him power over others. But the law doesn’t care about your money. It doesn’t care about your labels or your brand. The law cares about respect, about dignity, and about the truth.

I sentenced Carter to six months of community service. Not the kind where you show up for a photo op, but real work. He would spend 30 hours a week cleaning toilets, picking up trash, and removing graffiti at city parks and transit stations. He would do this under the supervision of Thomas Briggs at the Providence Department of Public Facilities. And once a month, he would work alongside Luis Rivera, under supervision, at Harbor Tower.

I looked at Carter. “You wanted a viral moment. You got one. But you didn’t get to choose how you’d be remembered.”

Carter’s father, Richard Winslow, arrived shortly after, and I could see the weight of the moment hitting him. He wasn’t angry with me or with the court. He was ashamed of his son. And when he told Carter, “You’re going to do it. If you don’t, I’m freezing the trust distribution,” Carter knew this wasn’t something money could fix anymore.

Carter’s arrogance had led him to this point. He thought he could buy respect. He thought he could mock others without consequences. But in the end, it wasn’t about money. It was about what kind of person you choose to be when you think no one is watching.

I left the courtroom that day with a quiet satisfaction. Justice had been served, but more importantly, Carter had been given the opportunity to learn a lesson that many never get the chance to. A lesson about humility, about dignity, and about the real price of respect.