My Scam Story #56

I’ve been calling myself every name in the book for days, so you don’t need to. I know I messed up, and I’m still kicking myself over it. But I’m sharing this because I don’t want anyone else to fall into the same trap I did. Here’s how it all went down.

I volunteer every week at a small church in St. Petersburg, Florida, helping with community outreach. A few months ago, I started noticing a guy who showed up regularly. Let’s call him Tom. He looked rough—worn clothes, tired eyes, like life had beaten him down. He said he was homeless, and my heart went out to him. Whenever we had meals at the church, I made sure he got a plate. He’d often ask folks for a few bucks, and the church even took up collections for him sometimes. I learned he was an ex-convict, trying to get back on his feet. Our pastor eventually warned us to stop giving him cash because he was double-dipping—asking the church and then hitting up individuals. I should’ve listened, but I didn’t.

One Sunday, Tom asked if I could give him a ride to the motel where he was staying, a rundown place off 34th Street. I said sure. When we got there, he said he was short on cash for the room and some food. He looked desperate, so I handed over $50. He paid for the room right in front of me, which made me feel like I’d done something good. Then he asked for my number in case he needed help again. I gave it to him. Looking back, that was my first big mistake.

On the drive, Tom opened up. He said he’d just landed a job and was expecting a big inheritance from his late father—enough to turn his life around. I was happy for him, didn’t think much of it. He promised to pay me back the $50, but I brushed it off, saying it wasn’t a big deal. I just wanted to help.

That night, my phone started blowing up. Tom was texting me nonstop, saying he needed money for equipment for his new job. “I’m gonna lose this before I even start,” he wrote, sounding frantic. I should’ve seen the red flags, but instead, I felt bad for him. I sent him $200 through a cash app, thinking I was saving his job. He swore he’d pay me back once he got his first paycheck.

A few days later, he called me while I was at work. He was panicking, saying the police had shown up and he owed $275 for some registration issue from his past. I didn’t ask enough questions—I just sent the money, worried he’d end up in jail.

This went on for weeks. We had a hurricane warning in the Tampa Bay area, and Tom said he needed cash to stay in a hotel to ride out the storm. I sent $300. Every time he asked for money, it was a new crisis. One day, it was $400 to keep him off the streets. Another, it was $600 to secure his inheritance, which he kept saying was “almost here.” He’d update me constantly about this supposed windfall, how it was tied up in legal stuff but would come through any day. I believed him because I wanted to believe he was turning his life around.

He even gave me a specific date when the inheritance would hit. He said he’d pay me back everything—over $10,000 by then—and throw in extra as a thank-you. I told him I just wanted what I’d given, but he insisted. When that day came, surprise, surprise—another crazy story. Something about a lawyer screwing up the paperwork, and he needed $800 to fix it. I sent it, thinking if I didn’t, I’d never see my money again.

That’s when the scam shifted. It felt like I was trapped. Every new request came with a threat—if I didn’t send money, he’d be stranded, lose the inheritance, and I’d be out everything. I was in too deep, chasing the hope of getting my money back. The amounts kept climbing: $500 for a “legal fee,” $700 for “emergency travel.” By the time I stopped, I’d given him nearly $15,000 over two months.

I finally broke down and told my sister and a close friend. They were shocked and told me to cut him off immediately. I felt so stupid, but their support gave me the push I needed. The next time Tom called, I told him I was done—no more money until he paid me back. He didn’t stop. He kept spinning wild stories, even claiming his life was in danger without another $1,000. For the first time, I said no. He got angry, saying I’d never see my money and threatening to call my parents to “tell them everything.” I told him my family already knew, and he backed off, saying it was “just a civil matter” and I couldn’t do anything about it.

I’ve spent a lot of time replaying this in my head. I thought I was helping someone in my community, doing something good in the name of faith. Tom leaned into that, always talking about God’s will, how my help was a blessing. I ate it up, thinking I was making a difference. No religion asks you to drain your savings for one person, but I let my guard down. I ignored the warnings, the inconsistencies, the gut feeling that something was off.

Writing this makes me feel exposed, like I’m admitting to the world how naive I was. But if it stops even one person from falling for a similar con, it’s worth it. People like Tom prey on kindness, spinning lies so convincing you don’t see the truth until it’s too late. There are real people out there struggling, and I wish I’d given that money to them instead. I’m trying to move on, to learn from this without letting it define me. It’s hard, but I’m getting there.