Conning a Con Artist

Conning a con artist isn’t your run-of-the-mill operation. These guys live and breathe deception, so trying to pull a fast one on them requires a different level of finesse.

First off, understand that a con artist is always on alert, constantly scanning for signs of a setup. This means you need to come at them from an angle they don’t expect, something that doesn’t trip their usual alarms. The key is subtlety - don’t approach them like a typical mark. Instead, play on their arrogance. Most con men believe they’re smarter than everyone else, so let them think that. Let them underestimate you.

The best way to do this is by using misdirection.

While they’re focused on one hand, you’re working the other. A classic approach here is to appeal to their greed. Con men are often driven by the thrill of the score, the bigger the better. You want them so fixated on a tantalizing prize that they miss the trap you’ve set. But the bait has to be perfect - not too easy, or they’ll smell a rat, and not too hard, or they’ll lose interest. This is where your research comes in. You need to know what makes this particular con artist tick, what their weaknesses are, and what they can’t resist.

Another critical tactic is the use of false flags.

You let them think they’re the ones running the con, that they’re the predator, not the prey. You create a scenario where they believe they’re stringing you along, but all the while, you’re the one pulling the strings. This requires patience and a bit of acting. You need to be convincing enough in your role as the mark that they drop their guard. Feed them just enough to keep them interested, and then slowly reel them in.

Timing is crucial.

A con artist knows how to play the long game, so you’ve got to be even more patient. You need to strike at the perfect moment - when they’re confident, when they’ve fully committed, and when they’re least expecting it. If you move too soon, they’ll get suspicious and bolt. If you wait too long, they might catch on or lose interest. It’s a balancing act that requires you to read them like a book, understanding their tells and tendencies.

You also need to have a solid exit strategy.