I have an unwholesome interest in scams.
A call from a boiler room
One day back in the 20th century I got a cold call from a young lady working in a boiler room somewhere. She had an Exciting Offer for me. She talked through her script with earnest, clumsy enthusiasm. I let her run for a minute, then gave her a couple of softball questions, which she fielded by awkwardly reading scripted answers. Then I took a guess.
“Is today your first day at this job?”
“Yeah, sorry, I’m still learning.”
“No harm done. You’re doing great. But can you tell me how your employer makes money from this?”
She started to paraphrase the rap from her script, but I interrupted her. “No, that is not how they make money.” Then I explained the scam to her.
She paused a long moment. “Wait. Really?”
“Yeah. Now, I don’t want to tell you what to do. Working this kind of job is a bummer. You wouldn’t have taken it if you didn’t really need the money.”
“I sure do.” She said it with conviction I was glad she could not muster when reading the script.
“So think about this. Your employer is lying to me in order to rip me off. Are you sure that they will keep the promises they made to you?”
“Oh.”
“Hang in there. And have a good day.”
“Thank you.”
I felt like a hero.
Short con on the street
One day I was walking up Powell Street in San Francisco, near Union Square, among the tourists. A man in a nice suit and no necktie approached me. He sheepishly confessed to being in a jam; things had gone sideways for him, his wife & kid were holed up in a hotel room, and he needed a little money to get his car and them back on the road.
He was good, but I made him work for it with some pointed questions. He had great answers, and he really sold the mix of anxiety and embarrassment. I gave him forty bucks, and he handled the blow beautifully — grateful and eager to go sort out his troubles. Worth every penny.
Maybe six or eight years later, I was walking up Powell again, and I saw him scouting the crowd; he was even wearing the same suit. I hoped I might get to see him work someone else. But instead he approached me. I understood him not recognizing me; the last time I had been clean-shaven, with my hair tied back, dressed casually, while this time I was beardy with my hair down and wore a good suit.
It was uncanny having him give me the exact same pitch again. I drew out my wallet, pulled out a couple of twenties, grinned, and said, “You told me the same story right here on Powell Street years ago; I gave you forty because I admired your craft. I’ll give you another forty now if you tell me why you marked me.”
He tried to bluff past it. He didn’t know what I was talking about, he had to get back to his wife and kid, blah blah blah.
“No, I already heard that one. But I really will pay to hear what about me got you to choose me as your mark,” I said cheerfully.
His demeanor changed. He was sorry he had bullshitted me. The reality was that he was in a different jam, but he figured the wife and kid thing would be more convincing. He started to lay out this whole different story.
“That’s not what I asked.” I waved the money. “Satisfy my curiosity, or don’t.”
His demeanor changed even more sharply. He was suddenly in tears. He was desperate because he was in trouble. He trembled. The guy was good. I feigned a sympathetic expression and enjoyed him working it for half a minute. But I pulled my hand with the money closer to me.
“Heartbreaking,” I said. “But not what I asked. It’s easy money. Do you want it? Tell me how you marked me.” I expected a lie, but was ready to enjoy one.
He stopped the shtick, suddenly and completely. He was expressionless, and for a moment he met my gaze with a psychopath’s dead eyes.
Then he just walked away.