My name is Anthony Romano. What Preston Whitfield IV didn’t know was that his family’s $4.2 million mansion was mortgaged through my bank. You see, Preston thought he was bullying some poor pizza shop owner. Instead, 24 hours later, he was staring at foreclosure papers. Sometimes the most dangerous people are the ones who look harmless.
I stayed completely silent during his racist rant. I nodded politely when he threatened to cancel my daughter’s wedding, and then I made a decision that would destroy his entire world. By the way, if this story sounds familiar, maybe you’ve dealt with entitled people who think money makes them better than everyone else. Hit that subscribe button.
I’d love to know where you’re watching from, especially if you’ve ever been underestimated because of your background. Trust me, you’re going to want to hear how this ends. It all started eight months ago when my daughter, Anna, brought home her fiancé.
Anna had been dating Preston for eight months when she finally brought him to our house in Federal Hill. I could see the disappointment in his eyes the moment he stepped out of his BMW and saw our neighborhood. Row houses, small yards, working families.
I was wearing my usual Saturday clothes: jeans and a Providence College t-shirt that had seen better days. My 1995 Honda Civic, with 240,000 miles, sat in the driveway next to his spotless car.
«So, you’re Anna’s father,» Preston said, extending a manicured hand. His Hermes belt probably cost more than most people make in a week.
«Anna tells me you work in finance?» he asked. I noticed the pause, the careful word choice.
«I work at a bank, yes.»
Anna jumped in quickly. «Dad’s being modest. He’s been with the same company for 25 years.» What she didn’t know was that I owned that company.
Preston’s smile was the kind rich people give to service workers—polite and distant. He glanced around our modest living room, taking in the worn furniture, the family photos on the mantel, and the framed picture of Anna’s Stanford graduation.
«Stanford,» he said, examining the diploma. «Impressive. Must have been quite an investment for your family.»
The way he said «investment» made it clear he thought we’d struggled to afford it. He had no idea I’d paid her full tuition for four years—$320,000—without touching a penny of my real assets.
«Anna worked very hard,» I said simply.
«Of course. Merit scholarships help so much, don’t they?»
Anna’s face reddened. She’d never told him about any scholarships because there weren’t any. She thought her father had taken out loans and made sacrifices, not knowing that Stanford’s yearly tuition was less than what Romano Financial made in an hour.
«Dad,» Anna said quietly, «Preston’s family is hosting an engagement party next month at the Yacht Club.»
«The Newport Country Club,» Preston added. «Been in my family for four generations.» He was marking territory, establishing a hierarchy: old money versus whatever he thought we were.
«That sounds wonderful,» I said.
«It will be,» Preston replied. «Though I have to be honest, Mr. Romano, Anna and I have been discussing the wedding, and we have some concerns about the venue situation.»
Here it comes, I thought.
«Anna showed me the reception hall you suggested, Russo’s on Federal Hill,» he said, pronouncing it like it was painful. «I’m sure it’s adequate for certain celebrations, but our guest list includes partners from my law firm, family friends, and business associates—people who expect a certain standard.»
Anna looked mortified. «Preston, we talked about this.»
«I know, sweetheart, and I want to make this work. But we need to be realistic about what kind of wedding represents both our families appropriately.» He meant his family; ours was just along for the ride.
I kept my expression neutral, but inside, something was shifting. I’d spent 15 years building Romano Financial from a single storefront loan office to 80 branches across New England. I’d done it quietly, deliberately, always staying below the radar. Anna thought I was just another bank employee because I wanted her to succeed on her own merit, not because of my money. But watching this entitled kid dismiss my daughter’s happiness for the sake of his social status was testing my patience.
«What did you have in mind?» I asked.
Preston brightened. «There’s a beautiful venue in Newport, Oceanside, where people like us typically»—he caught himself—»where the ceremony would be more appropriate for our combined social circles.»
People like us. Not people like me. He had no idea what people like me could really do.
The call came on a Tuesday evening while I was reviewing quarterly reports in my home office. Anna’s voice was strained. «Dad, can you come over? Preston and I need to talk to you about something important.»
Twenty minutes later, I was sitting in their Cambridge apartment, a place I’d helped Anna secure, but she thought she was renting with student loan money. Preston had clearly been pacing. His usually perfect hair was disheveled, and his tie was loosened.
«Mr. Romano,» he began, «I want to be direct. Anna and I have been looking at wedding venues, and we found the perfect location: the Chandler at Cliff Walk in Newport.»
I knew the place. Oceanside elegance. A $1,500 per person minimum.
«It’s beautiful,» Anna said quietly, «but it’s expensive.»
«How expensive?» I asked.
Preston cleared his throat. «For the guest list we’re planning, 200 people, the total would be approximately $300,000.»
Anna’s face went pale. I could see her doing the math, thinking about her father’s imaginary bank salary and wondering how we’d possibly afford it.
«That’s quite a bit,» I said.
«Which is why,» Preston continued, «I’ve been thinking about how to make this work for everyone. My family has connections at the venue. We could potentially get the cost down to, let’s say, $50,000 from your side.»
Fifty thousand dollars, like he was doing us a favor.
«The thing is,» he went on, «this really needs to be decided soon. The Chandler books up years in advance. If we don’t secure the date this week, we’ll lose it.»
It was an ultimatum wrapped in urgency. Anna was staring at her hands.
«Dad, you don’t have to—»
«Actually, I do,» Preston interrupted. «Anna, sweetheart, you know how important this is to both our families. My parents have already started planning. They’ve invited the senator, the mayor, and partners from three law firms. This isn’t just a wedding; it’s a networking event that will benefit both of us for years to come.»
Both of us. Again, he meant himself.
«And if we can’t make it work?» I asked.
Preston’s mask slipped for just a moment. «Well, then we’d have to seriously reconsider our timeline. Maybe postpone until we can find something more financially feasible.»
The threat was clear: $50,000 or no wedding. Anna’s eyes filled with tears.
«Preston, you’re putting my father in an impossible position.»
«I’m being realistic about our situation,» he replied. «Anna, your father works at a community bank. He’s probably making, what, $60,000 a year? Asking him to contribute $50,000 to a wedding is already generous, considering the proportional investment.»
Sixty thousand dollars a year. If only he knew. I watched my daughter’s face crumble. She was caught between the man she loved and the father she thought couldn’t afford to give her the wedding of her dreams. What she didn’t know was that $50,000 was what Romano Financial made in less than three hours.
