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Love of the game
Americans have always had a soft spot for con artists. But will the honeymoon soon be over?



A short while ago, a man walked into a Boston police station bearing good news and bad news. Apparently, as a demographic, police officers are not very adept at keeping up with their cell-phone payments. The bad news was that the man — we’ll call him Bob — was there to collect outstanding phone bills. The good news was that the company Bob worked for — a collection agency — was offering a one-time-only deal. If the officers coughed up immediately, they would have to pay only a fraction of what they owed.

The opportunity seemed too good to pass up, and by the time Bob had finished brandishing his brochures and business plans, many of the cell-phone deadbeats wanted in. Forms were signed. Bills were paid. Receipts were shown. Cash changed hands. Bob was gone. A few weeks later, however, some odd things started happening. Cell-phone bills continued pouring in. Worse still, there were rumblings of fraud. The officers’ bills, it turned out, had been paid with a dodgy credit card. Somebody call the police! Oh, wait ...

Chances are, as you read this you are not shaking your head and tut-tutting. Chances are, you are smiling. This, after all, is a great con. Bob was clearly a pro: he did research, he used props, he had a great line of patter, and he had balls the size of a Volkswagen Bug. You’ve got to love him.

Indeed, no matter how much we’d gripe and groan if we were to get taken like this, most of us delight in a clever, well-executed con. We are especially delighted when the trick targets someone seemingly unconnable. We are left with a feeling of amazement and wonder, not unlike the feeling we get when we see David Copperfield make the Statue of Liberty disappear — “How did he do that?” With his cell-phone scam, Bob hit con-game pay dirt. As Boston fraud detective Steven Blair says, “It must’ve been a thrill pulling one over on the cops.”

Quite. But not such a thrill for the cops, maybe. For one thing, they know they’re unlikely to get much sympathy, even from their fellow men in blue. “If you fall for this stuff,” says a local officer, “Jesus, what kind of dope are you?”

The truth is, you don’t have to be a dope to fall for a con trick. As with many crimes, there’s a temptation to blame the victim, to comfort ourselves with the notion that we would never fall for something like that. But anyone can get taken, even trained police officers. Actually, cops might be especially vulnerable. Scam artists prey on complacency, and cops have that attribute built in.

Scam artists also prey on greed, the desire to get something for nothing; and Bob’s cell-phone suckers were not immune to that. Who is? If someone offers you free money, why, you take it. The only catch is, con games are invariably set up in such a way that to make (or, in the cops’ case, save) money, you first have to part with money. It’s a proposition that should set the alarm bells ringing, yet people have been falling for this stuff for millennia. Why?

First, we have to take a look at what a scam is. This is more difficult than it sounds. The con game is a nebulous thing. Even the law doesn’t have a firm grip on what constitutes a scam. Sometimes it’s treated as larceny, sometimes as fraud. Basically, a crime becomes a con when there is some sort of systematic trickery involved — when confidence is won through dishonest means. Hence the name.

Because of its amorphous nature, the con game is a crime without a jurisdiction. A list of the agencies that investigate and prosecute scams reads like a bowl of alphabet soup: FTC, FBI, SEC, AG, BBB, SPD ... With so many agencies punishing so many scam artists for so many crimes, it’s tough to attach figures to current trends in scammery. According to the Alliance Against Fraud, the con game is a $40-billion-a-year industry. And anecdotal evidence suggests that scam artists are at large in record numbers.

Last year, according to the Cambridge Police Department, the city saw a rash of “brick in a box” scams. In one incident, a guy called around saying he was a Best Buy manager. For cash up front, the guy said, he could arrange a nice little deal on a computer. One potential victim grew suspicious and called the cops, who arrested a 29-year-old Medford man. A surprising number of people, though, fall for scams like this, paying good money for boxes stuffed with bricks, newspaper, and blocks of wood.

Jesus, what kind of dope ... This is a common response. But you have to take into account a true con artist’s talent. A good grifter is an actor, a novelist, a salesman, a psychologist, a psychic, an illusionist, a motivational speaker, a mentor — in other words, a skilled liar. A scam artist can impress the hell out of you or have you weeping with pity. Con artists seem to put their trust in you, so you are more likely to put your trust in them. They can make an opportunity seem irresistible and almost out of reach. The very cleverest will have you clamoring for a piece of the action.

“They don’t take people’s money,” says author Robert Jay Nash, who has written extensively on confidence tricks. “It’s foisted on them. The best cons are set up like, ‘Get away from me, why should I let you in?’ You don’t part with your money, you’re begging him to take it. It’s a human trait: the more you are denied something, the more you want it.”

In the grips of a skilled con artist, everyone is a potential victim. And for the artist, the smarter the mark, the bigger the thrill. According to Cambridge Police sergeant Frank Pasquarello, for instance, rings of grifters who delight in scamming MIT and Harvard students have recently been operating in Cambridge.

“Con men have a perverted sense of humor,” says Nash. “They feel superior to the top deans at Harvard and Yale, because these [academics] may have the intelligence, but they don’t have the moxie to go out and put it to the test.”

And this fact isn’t lost on the rest of us. “We have a secret admiration for con artists,” Nash says. “We get a vicarious thrill.”


Con artists have long provided fodder for Hollywood. We chuckle at the horseplay of Michael Caine and Steve Martin in Dirty Rotten Scoundrels. We thrill to Anjelica Huston’s sultry prevarication in The Grifters. And we marvel at Paul Newman and Robert Redford’s elaborate antics in The Sting.

Indeed, The Sting makes explicit our secret admiration for con artists, portraying them as both lovable rogues and avenging angels. The Sting’s dashing grifters use their talents to punish a vicious mobster. They emerge as righteous heroes. It’s a fist-pumping, Chariots of Fire–type film.

Local playwright David Mamet’s forays into the con-trick genre — The Spanish Prisoner and House of Games — take a darker view. The snarls of trickery and counter-trickery in those films are tinged with a dark undercurrent of dread; they end up asking questions like Can we ever truly know another person? Even Mamet, though, seems to delight in the complexities of the game.

It’s no surprise that The Sting is the most gung ho of the con-trick flicks. The film takes place in the Jazz Age, the golden age of grifting. Prohibition America — with its underground, cash-only economy — proved to be fertile ground not only for violent thugs, but also for the double-dealing smart alecks who hovered around them.

The most inspired scam artist of that era was the Chicago-born Joseph “Yellow Kid” Weil. In the course of his long career, the Kid elevated the con game to the realm of the sublime, and became a folk hero in the process. Once, he fabricated an entire bank in Muncie, Indiana, in order to bilk a millionaire businessman on a phony land deal. It was a marvelously orchestrated illusion — the “bank” came complete with customers (local prostitutes) and tellers (racetrack touts); even small details like deposit slips were taken care of. As Nash puts it, “By the end of that day, Weil was far from Muncie with $50,000 in his pocket.”

Nash, who claims to have known Weil, betrays a not-so-grudging admiration for the man he calls “the greatest con artist of the 20th century.” “He was very brainy, extremely intelligent,” Nash says. “He could have made millions of dollars if he’d followed a legitimate pursuit. But that’s not what gave him the kick. He took particular joy in hitting the greedy mark. [The Muncie victim] was a greedy, vicious man who paid slave wages to his employees.”

Weil was indeed a wily character: when the mark came into his mock bank bearing $100,000 in a suitcase, Nash says, Weil would accept only half of it, insisting that he had another investor to put up the remaining cash. Thus the victim parted willingly and swiftly with his money.

“The confidence game is the great game,” Nash says, “especially if you can take someone who’s wealthy, greedy, and arrogant. Those are the people that these guys love to take.”


Nash, of course, is buying into a sentimental view of the game. There is no code of honor among scam artists, and there never was. There is, however, an element of divine justice to the best con tricks. The most popular street scam in the Boston area right now — the pigeon drop — is a perfect example of the retributional grift.

In the pigeon drop, a grifter — usually a woman — will approach another woman and strike up a conversation. She might start talking about her kids, her life in the suburbs, trouble she’s having with her car. Once a rapport has been established, the grifter will make a jittery confession: she just found a bag of money — $10,000! — and she doesn’t know what to do with it. She’d like to keep it but she’s kind of scared. She shows the mark a wad of cash (one-dollar bills flanked by 20s). It looks like it might be drug money or something. She’d be a lot happier if she had an ally in this. Would her new friend be interested in sharing the money?

Bloody right she would.

Once the mark has been drawn in, the grifter will offer to call a lawyer friend for advice. She hands over the money (creating an illusion of trust: either she’s switched the bag or she has a confederate keeping watch) and exits left, returning a few minutes later with splendid news. The lawyer will hold the money in escrow for a 20 percent cut, to be paid up front. If no one claims the money, the two women get to share it. When the victim antes up her half of the lawyer’s cut, the grifter takes off, leaving the victim alone, confused, and broke.

“Don’t pity the victim,” grumbles Nash. “Nobody falls for that stuff unless they’re greedy. There are people who take out life savings because of a pigeon drop. I have no sympathy, none. I don’t care if they’re little old ladies. They had it coming.”

Pasquarello agrees: “I blame the people giving up the money as much as the artist,” he says. “The victims are the ones who allow this sort of thing to go on by their greed. Sometimes it’s hard to find a nice word for someone who’s trying to make a quick buck at the expense of others.”

Indeed, victims of pigeon drops lose money because they tried to deprive someone else of theirs. This rough justice, though, is not motivated by the scam artist’s moral sense. The pigeon drop, like all the cleverest scams, implicates the mark in impropriety because this helps the grifter make a clean getaway. After all, how is the victim going to explain this one to the cops?

And when people do report these sorts of scams, they get little respect. Detective Blair recalls the time a judge remarked, looking down his nose at a couple of con victims, “I don’t consider them victims.” This attitude pervades the legal community, often leading to less-than-vigorous responses from police and relatively lenient sentences from judges, who figure that the victim ostensibly parted willingly with his or her cash.

As Pasquarello puts it, “With a con, no one’s been shot, stabbed, or hit with a brick.”


Not every police officer has such an accommodating approach to the game. Blair, a 19-year veteran of the Boston Police Department’s Major Case Unit, is the busiest fraud investigator in Boston — and possibly the country — averaging, he says, between 150 and 200 arrests per year. “I don’t want to pat myself on the back,” he says, “but I’ve got a knack for it. It’s my calling. I guess I’m the guy to go to when it comes to fraud.”

Part of the reason for Blair’s success is that he has learned to play con artists at their own game. That is, he thinks like a grifter. “I’m as bad as they are,” he says. “I love the game. It’s like chess — it’s a challenge. I just love playing the game.”

Blair is an unremarkable-looking man: middle-aged, medium height, medium build, brown hair. He’s the kind of guy who would blend instantly into a crowd, and that’s exactly how he likes it. It takes a sneak to catch a sneak, and you can’t sneak around if you’re pulling Dirty Harrys all over the place.

Despite Blair’s unassuming appearance, however, there’s something about him, a flinty self-assurance. You’re not sure why, but you would not want to get on the bad side of this guy. Maybe because you sense that he would chase you to the ends of the earth. “You never give up,” he says. “You just keep plugging away.”

Even Blair, though, has a soft spot for the people he arrests — his “customers.” “The good scam guys, I’m the first one to give them credit for their work,” he says. “But I’m also the one who tells them when it’s time to pay the piper.”

Blair admits to a grudging respect for Cristal Campbell, whom he collared last year for scam-based crimes. “She said, ‘I’ll be out by morning,’” he recalls. “I said, ‘No you won’t; you’ve got 50 warrants out on you. You won’t be going anywhere.’”

At her arraignment, Campbell apparently went into labor. A puddle of amniotic fluid formed at her feet — except it wasn’t amniotic fluid, it was pee, and Campbell’s subsequent trip to the hospital turned out to be a flight to freedom. Though she’s been arrested three times since, Campbell is currently at large. “That woman,” Blair says, “makes a lot of money.”

The financial aspect of his job gives Blair acid reflux. “It drives me crazy,” he says. “These guys have wide-screen TVs, DVDs, a brand-new Lexus in the driveway. It got to the point where I bugged my wife for two years to get me a wide-screen TV. I had to level the playing field.”

Suddenly, a big smile. “Greed always gets them in the end,” says Blair. “I love to catch them when they think they’ve got away with it.”


“I thought I’d got away with it,” says Jake, 51, one of the most prolific, if not elusive, con artists in town. Jake is an old-school career con man, the kind who will sell you the bar you’re drinking in. “The con man’s mind,” says Jake, “is always working.”

This man, it has to be said, is no Robert Redford. But he probably wouldn’t mind my saying this. A scam artist should not stand out. Jake has cropped gray hair. His demeanor suggests an odd mix of diplomat and townie. He’s perfectly likable. Beyond this, it’s hard to find anything to say. Except that he is no slacker when it comes to cons.

In the course of his 30-year career, Jake has pulled just about every trick imaginable, making over a half-million dollars in the process. Jake does not, though, consider himself to be a particularly bright person. “It’s not how smart I am,” he says, “it’s how fucking stupid people are. It’s almost a joke. How much of an asshole is this person? It amazes me.”

Once, Jake sold a golf course — or at least got a couple of guys to put down a deposit on one. “I found a real couple of pigeons there,” he says, smiling. “I took $20,000 apiece from them.”

He thought he’d got away with it. He hadn’t. “Ironically, I got caught on a golf course,” he says. “I was playing a round and there was a cop playing behind me. He recognized me and arrested me on the spot.” Jake ended up serving six years for that one. In all, he figures, he has spent 25 years behind bars. “What a waste of a life.”

But Jake’s regrets aren’t only for himself. He recalls with scorching shame the time he scammed scores of friends and acquaintances at his local bar. “I told them we were going skiing in Austria,” he says. “They showed up at the bar one morning with their skis. Twenty years later, I can still see their faces in my mind. I still feel awful.”

“I think he’s getting tired,” says the superintendent of the jail where Jake is currently locked up. In a month, Jake says, he’s getting out, and then he’s through. “I’ve lost the thrill,” he says. “No question in my mind, I’m done. It’s time to go home.”

Home, however, may not be the best place for Jake to end up. “Every time I see someone I recognize, I think, ‘Is this good or bad?’” he says. “‘Did I get that person?’ It makes you paranoid.” Still, as the old saying goes, just because you’re paranoid doesn’t mean they’re not out to get you.

One night a few years back, Jake says, he was leaving a bar in the North End when he was jumped by a couple of old marks: “Two gentlemen put a gun to my back, tied my hands up, put rocks in a glove, and crushed my cheekbones.” After this, they pistol-whipped him and threw him in the harbor. “If it had been high tide,” he says, “I would have been dead.”

Okay, maybe quitting isn’t such a bad idea. But what does a retired con artist do? “I’d probably make a terrific salesman,” Jake says, “something dealing with the public.”

He adds: “I would like people to trust me.”

Robert Jay Nash isn’t convinced that people like Jake can be reformed. “Con men are incorrigible,” he says. “They are 100 percent recidivist. Their psyche demands they do what they do.”

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