In the parlance of the confidence game, an insider is a type of con man, or, more accurately, a role a con man plays in the big game. Arguably, the insider is himself a shill, although the role is more complex and the rules certainly change when a shill acts as an insider.

The role of the insider varies from game to game, but, the defining characteristic is that the insider allegedly has specific access or information which can make the mark (and, ostensibly, the roper and possibly a few shills) rich. Or, at least, richer. So, generally speaking, the insider is the mark's liaison to this special condition, called the little game.

In a long con, the roper brings the mark in for the meet. This is the mark's first chance to test out whether the roper's pitch is true. At the point when the insider comes into the game, the mark is asking himself if the little game is too good to be true. He's asking himself if the risk is too great. If the roper does his job well, the mark is also asking himself what he will have to do to get in on the game. The insider must speak to these questions.

More than the roper, the insider must look the part. The smart con man will look beyond simple costumes and deep into what's convincing instead of what's merely expected. If the insider is an investment broker, should he wear a three-piece suit or a shitty polyester blazer and a pair of beat-up penny loafers that don't match his belt? Should he be thin and well-toned or fat and sloppy?

Often, it pays to let the mark convince himself. If everything is contrived to meet expectations, that may never happen. Compare these two scenarios:

  • The mark is brought into a busy investment house. He is marched past cubicles of secretaries, rooms with file cabinets, and back into a beautifully appointed office where the powerful-looking insider waits for him with high-grade scotch whiskey and a firm handshake. The insider, with the help of the roper, primes the mark with a glad hand and a smile. A number of gleaming degrees hang in an alcove. A top-of-the-line computer with a flat screen sits on the desk. The mark's concentration hardly wanders. Everything is perfectly convincing.

  • The mark is brought to a small suburban home, modestly appointed. An intolerably chatty wife gives the mark and the roper egg salad sandwiches that are too salty and offers them some Jack Daniel's. The insider is outside mowing the lawn, and comes in after a few minutes in a sweaty and somewhat banal T-shirt. The insider, the roper and the mark go back to the insider's office, where an MBA from a mediocre college hangs on the wall. An underpowered computer sits on the desk with an heavy, dusty CRT monitor. The insider steps outside with the roper and, in an audible but muffled conversation in the next room, the insider chides the roper for bringing this stranger to his house. The roper, with some difficulty, "convinces" the insider that the mark is "cool". A few reservations are quelled with similar difficulty. Perhaps the insider "owes him one". Certainly, the insider stands to gain a cut from the mark's participation. The roper talks the insider into letting the mark into the little game.

    Meanwhile, the mark is left in the office to snoop a bit. The room is well-dressed by the grifters. Business cards, a desk calendar, a photo from the company picnic, a cheap "15-years of Service" anniversary award may sit on the bookshelf. A foam-rubber stress ball with the company logo looks well-used. Perhaps there are a few memos from an overbearing boss that lend credence to the insider's (supposed) treachery to his firm. Maybe an e-mail from a secretary with subtle undertones of an affair, giving more human depth to the insider.

When the mark goes home, excited by the prospect of a sudden boost in his income, he can't sleep. He lies awake thinking about the meet Which scenario is more likely to quell the (possibly paranoid) questions that arise in his mind? Which scenario answers the most questions? Which scenario makes it more plausible that the mark, the roper, and the insider are even doing business together in the first place? Which image of the insider is easier to dismiss as "couldn't possibly be a con man"? Finally, since the confidence game is designed to make money for those involved, which scenario is less expensive to set up?

Frankly, either scenario could be successful. Some marks are so blinded by the glare of a clean glass-and-steel office building that they don't ask themselves the questions the second scenario is designed to answer. To a career con-man, however, minimizing expense and minimizing risk are watchwords of the profession.

The insider's role and his surroundings include several important processes, some of which are hinted at in the above scenarios:

  • The insider doesn't always seem glad to meet the mark. The insider often cautions the mark repeatedly about the risk. The insider may try to back out of the deal. The insider rips up the mark's bank check (sometimes called the tear up). This process is referred to as red inking. The insider pretends to try to pull the fish off the hook. This makes the mark's involvement his own idea. When, finally, the insider agrees to let the mark into the game, the mark feels as though his has gained the confidence of the insider. As David Mamet's character Mike states in the seminal 1987 con movie House of Games, "It's called a confidence game. Why? Because you give me your confidence? No. Because I give you mine."

  • Sometimes a convincer is required. The mark might show some doubt, so his is allowed to risk a little on the little game and makes a little more than his money back. Once he's got his taste, the theory goes, he'll be ready to risk big. The insider and the roper put him on the send: he goes to his bank or his wife or his mommy to bring in the prize (also called the nut, the take, the score or the touch).

    My advice to you, dear reader: should you ever find yourself far enough along in a con that you're given a convincer, and you make the con artists for what they are, don't be "wise" and try to run out with the convincer. This makes every con man— from three-card monte throwers on up to the long con artists— angry. Don't think that because they are con men that they don't have muscle.

  • If a convincer is too risky, a stall might work just as well. The insider accepts a small amount from the mark and tries to "invest" it (bet it on a horse or a card game, buy stock with it, buy some commodity that can be turned around for a large profit . . . whatever the set-up dictates) but — OH NO! — somehow the transaction didn't make it through in time, the courier didn't arrive in time, the window closed. The stall lets the mark see what would have happened had the "investment" gone through. This is almost as good as a true convincer.

Often, once the "investment" is in the hands of the con artists, the insider is no longer needed. This point, (the hurrah) the crew just stands back and watches the sting and leaves the rest to the roper, or possibly a separate cooler (sometimes posing as a cop or fraud investigator) to cool the mark's beef.

In some instances, especially during the long con, a button takes place. This is designed to scare the mark away, leaving the take behind. Even better, If the mark thinks the insider and/or the roper are dead or in jail, he will probably give up hope and he'll be cool. Common button men:

  • Police (con men in police clothing) bust the insider and/or the roper and/or one or more shill, but the mark escapes.

  • Violence flares up and someone gets shot and/or killed. If it can be engineered convincingly, the mark himself may be the cause of it. Certainly, this is good reason for the mark to disappear.

  • The mark's fingerprints/signature/name/picture is somehow tied to the little game. Since the little game often involves some illegal graft, this generally scares the mark back into his normal life and out of the way of the con men.

Sometimes the term "insider" can also refer to someone on the inside of an operation, for instance:

  • A legitimate policeman or other law-enforcement officer on the take who can plant information in police files, provide stationery, badges, uniforms or assist the team in cooling the beef.

  • A sort of spy who provides bona fide inside information such as the disposition of a police investigation, investment information, or even communicates the moves of a mark inside of his own workplace, hotel or other venue.

  • Someone on the inside of a corporation who engages in less artful kind of fraud

For this reason, the role described at length above is sometimes referred to less ambiguously as the frontman, the hawker, the insideman, the primer or, in some situations, Mr. Big.



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