The Secret Life Of A Con Man: 'I Scam Innocent People For A Living'

GM, as we'll call him, once spent three weeks casing a mother of three, learning everything he could about her life, routine and preferences. When he finally found a way in, he robbed her of over $1,000. It was a good score. And because she was a piece of crap — GM concluded — the crime was justifiable.

He later found his research was flawed, however. The woman's husband had recently left her, burdening her with the care of three children. And she was in financial trouble. She wasn't so bad after all. So he gave the money back. Well, half.

"She deserved half," says GM, taking a sip of iced coffee.

"Did you drop the money in her mailbox or something?" I ask.

"I FedExed it to her." He grins. "With a note that said, 'A fool and their money are soon parted.'"

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Why am I having coffee with a grifter on a Monday night? Because he answered my Craigslist post titled, "Seeking a Con Artist for Interview." Because I figured there was no other way to get a con artist to open up, I offered $75 and anonymity.

"Okay, so I think you are looking for me," wrote GM in his response. "I do not grift honest people. That is my rule."

And that's how I met GM, a con man with a conscience.

GM had agreed to do an in-person interview the next morning at a coffee shop of his choosing, one with "good escape routes and foot traffic, so I can disappear if I feel you are not being forthcoming." He would approach me, he said, and he promised not to do anything slick. In his emails, he presented himself as principled: a Robin Hood-type who used cons to teach manners to the greedy.

With these types of people, simply explaining ethical behavior goes in one ear and out the other. But when you hit them in the wallet you have their complete attention.

"Don't be surprised if I am not who you were expecting," he continued. "You should check your initial thoughts or ideas as to what I am at the door."

"I will be as open-minded as I can," I wrote.

GM cancelled two hours later.

The next morning, GM called me from a blocked number to apologize.

"You know what?" he said, "I'm going out to dinner with my fiancé. How 'bout I pick you up after and we go have that conversation?"

Pick me up?

"Where do you live?" he asked. Stuttering, I suggested meeting somewhere besides my apartment.

"Okay, I'll grab you at six," he said. "Don't be late."

I was locking up my bike when I heard GM's voice fifty feet away. "Are you Dustin?" he asked from the driver's seat of his running car. A man on a bike across the street shook his head. GM had guessed wrong. It spooked him.

It looked as if he was about to drive away when I came around the passenger side of his car and knocked on the window. That really spooked him. But he didn't leave. He got out and scanned the road behind us, looking for irregularities and for cops.

"C'mon," he said.

I sat down and placed my bag in my lap. I tried to avoid any sudden or suspicious movements, so as to make it seem like I could be fiddling with a recording device or alerting law enforcement listening in on secret microphones.

GM was wearing dark sunglasses and a baseball hat. He looked like one of those concealed poker players on TV, the ones with tells to hide. He turned the car down a street and asked, "Am I what you were expecting?"

"I don't know what I was expecting."

What does a con man look like, I thought? GM was clean-cut and reasonably good-looking. He was even-keeled and rather pleasant, actually. But I could tell he was wondering if this risk was worth $75. A couple of minutes into the drive, we both loosened up. He started talking about the BBC TV show Hustle, and said it was a good portrayal of grifting.

I was relieved when we pulled up to a coffee shop about six minutes into the ride. I considered it Phase 1 in not ending up in a ditch that night. By the time he offered to buy me a coffee, I was pretty confident that GM wasn't a serial killer. He just tricked people out of money from time to time.

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I had wondered how GM finds his "dishonest" marks.

Gas station cashiers can't be trusted, according to GM. Some will take a winning lottery ticket from a customer, say it's not a winner and then throw it in the trash. When the "loser" leaves, the cashier reaches in the trash and claims the winning ticket. But the state publishes the names of cashiers who have gotten caught pulling this stunt. This is GM's black list. He uses it to give them a taste of their own medicine.

GM pulls one trick called the Pigeon Drop. It requires a $5 and $50 bill. He enters a coffee shop and introduces himself, makes small talk. Establishes trust. Then he comes back in later when it's busy. As he orders, he holds the $50 bill in plain sight, waving it around. When GM's sure the cashier knows it's a $50, he orders a coffee.

"When the cashier brings the order and looks at the $50 in my hand, I quickly order something else, like a blueberry muffin." Now that the cashier is sure GM will pay with a $50, he replaces it with the $5. He says he gets paid every time.

For GM, grifting is a family business. He told me that when he was young, the bank foreclosed on his father's home because of a glitch with the mortgage. Suddenly, GM, his father, mother and older sister were out on the street.

When GM's father couldn't find work, he joined a bank-robbing crew and started hitting armored cars. When his father got busted, the federal judge cleared out the courtroom and asked him to give up the members of his crew. He told the judge to go to hell. He got fifteen years.

In jail, GM's father shared a cell with a renowned grifter who taught him short cons like the Pigeon Drop and long cons involving larger sums of money, more players and higher stakes. When he was released, he started grifting, and sometimes brought GM's sister along. He kept GM out of it, not wanting to corrupt his youngest child, but the boy kept his ears open. He learned the Pigeon Drop, he said, over family dinner.

I asked him how he feels during a con like the Pigeon Drop. Do grifters get anxious? I asked if he experienced an adrenaline rush, and if he was ever scared.

"It's a touch of fear, a touch of happiness," he said.

GM didn't get into the con game right away. He said he listened to his father's stories for years before attempting his first grift. Even now, he prefers to minimize risk, to keep a low profile — to run the short con. GM is proudly small-time. Not so with his sister.

"I'll call her Katrina," he said. "She has balls. Big, brass, outrageous, like, no-problem-pick-pocketing-a-cop balls." He says he's scared of her. GM has rules, boundaries, certain things he just won't do. "Katrina," he says, "has no boundaries."

All the rules by which GM abides, such as avoiding honest people and not grifting people he knows, his sister couldn't give a damn about. For example, GM never enters people's homes. That's sacrilege, even if they're a lousy person. He quipped: "My sister would break into someone's house, sprawl out on the couch and watch pay-per-view."

"She grabbed this guy's wallet on the street once," he continued. "When he spun around and accused her of stealing it, she started screaming, 'This guy touched my bush!'" According to GM, avoiding a scene is an unbreakable rule in grifting. Not only did Katrina make a scene, she then ran into a nearby restaurant and called the police on the victim. She was gone before she was needed for questioning.

"She's incredible," says GM. "And smart, too. Her IQ is off the charts."

While GM's cons to supplement his income, grifting seems to be Katrina's full-time job. She's a natural deceiver, and everyone's a potential sucker, even their own father. She pulled one con where she pretended to enroll in a local college. She brought their dad to orientation, and would sit at the kitchen table on Sundays for hours, acting as if she was doing homework.

"My dad was writing checks for a year before he figured it out."

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GM says grifting requires discipline and patience. "Slight of hand is also important," says GM, referencing the Pigeon Drop. "You need to be good at misdirection, distracting a mark's attention at crucial moments. It takes practice.

"Know their routine, like when they pick up their kids, when they leave for work. The hardest person to grift is an erratic person. You can't predict what an erratic person will do."

Suckering a mark is all about gaining their trust and managing their perception of you. It's important that they develop their own ideas about you, rather than hearing them from you. "The best grift is to plant an idea in their heads."

Staying out of jail also requires discernment, being able to read a situation and bail if things don't feel right. GM likens himself to a wolf in this regard. On the hunt a wolf can't just pounce on anything that moves. It must discriminate, and cut a potential meal loose if conditions aren't right. This skill is lost on Katrina.

"My sister doesn't have the ‘cut and run' mentality. She thinks she can get out of anything." And she has, so far.

"But she's fixing to go down," GM admits. He's so afraid of doing cons with his sister that he has a rule to only pull one grift per year with her. He doesn't want to be there when the axe comes down.

GM never forgets the stakes. Years ago he gave his fiancé bail money in case he gets caught. "One slip up, it's game over."

He admitted to going twenty-two months without grifting. But he always comes back, partly because if he doesn't get greedy — i.e., sticks with the short con — he can fly under the radar and make easy money. But the scores don't seem significant enough to justify even minimal risk. $45 here, $100 there, maybe $1,000 if he risks a long con.

The juice, as the saying goes, doesn't seem worth the squeeze. Perhaps grifting satisfies some emotional need? An opportunity to be deviant, to screw the system, to stick it to a dishonest person? Maybe it's the rush: a touch of fear, a touch of happiness? Perhaps grifting is just in his blood. As any heir to a family empire knows, leaving the nest can be difficult.

If GM feels conflicted about his work, Katrina feels nothing. He's returned half of the money to a mark in dire straits; Katrina probably would have tried for more. Talking about her, GM uses phrases such as "lack of remorse," "fearlessness," "natural manipulator." I cautiously throw out the word "psychopath."

He didn't miss a beat. "She's a pure psychopath," he agrees.

She once planned a con called the "leukemia scam." She would shave her head, convince everyone in the community she was dying of cancer and then ask for charity. All because she needed money to go Jamaica.

When their father talked her out of the leukemia scam, Katrina settled for a con in which she slept with eight "boyfriends" and told them each not to wear condoms. Several weeks later she informed each man that she was pregnant and needed $500 for an abortion.

Like her brother, Katrina has all the cunning of a wolf, but none of the restraint. As her cons get bigger and more daring, she regularly exhibits the very character flaw GM seeks to exploit: greed. GM doesn't approve of a con like the leukemia scam because it takes advantage of people's compassion. Their father thinks it's gotten out of control. Even he admits that he may have created a monster.

Out of curiosity, I looked up the meaning of the name Katrina. It means pure.

No matter how small-time GM remains, he is always burdened by the possibility that his past will catch up with him.

"Grifting is not as glamorous as you may think," he says. "I constantly worry that I am going to cross paths with an old mark and it's a fear that returns every time I'm in a large crowd."

Interestingly enough, GM didn't guard his secrets. He gave them away, almost as if he needed someone to help shoulder the burden. Why else would he divulge such private information? It couldn't just have been for $75.

Where will he be in five years, I wondered? It seems inevitable Katrina would be staring at the inside of a jail cell. Unlike his sister, however, GM seems capable of change.

It had occurred to me that GM's whole story could have been fabricated. Perhaps I had been off the mark. GM seemed sincere, reflective, a decent guy on the surface. But was he a "good guy?" Or had he given me the kind of con man I needed to meet?

If GM's story had all been a lie, my hat's off to him. It was a stunning performance.

On the drive home, GM said I should try a grift myself. "Give the Pigeon Drop a try."

I said I would. I lied.

He turned the car onto my street. "Got something for me, bud?"

The stipend. Right. "Of course," I said, pulling a white envelope from my bag. He told me I could put it the middle console.

"Do you want to count it?"

"It's alright," he said. "I trust you."

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Dustin Grinnell is a writer based in Boston. His creative nonfiction has appeared in such publications as New Scientist, Vice, Outside Online, The Boston Globe, The Washington Post, The Philadelphia Inquirer, Writer's Digest, Salon and Narratively, among others. He is also the author of two sci-fi/adventure novels – The Genius Dilemma and Without Limits.

This article was originally published at Narratively. Reprinted with permission from the author.