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Finding a way into a criminal organization is about observing social dynamics. You start with a target. You're looking for just the right person to approach. People in the inner circle are usually too tough to go after - anyone with real power is bound to be cautious. Drivers and bodyguards are easier, but they usually don't have real access. You want someone with enough juice to be hungry for more, someone desperate to make a move. In short, you're looking for a frustrated middle manager.