The Inside Man is a particularly powerful piece to have on your side when planning any activity, let alone criminal activity. It gives you a viewpoint into the workings of the target, or enemy. It gives warning for the bad things being set up against you, and can give you the paths that need to be taken to avoid the pitfalls in your path. There isn't a crime I can think of that wouldn't benefit from an inside man to help pull it off. So, how do you go about getting one?
First You've Gotta Open Them Up
We talked about this a little bit with Fences, but one of the first things you need to do with an inside man is open them up. People are fundamentally simple creatures. We tend towards the path of least resistance, because it is easier. Answer me honestly, are you going to climb a sheer wall to go up six stories when an elevator is right there? Sure, some people might - and I would argue that those people are looking for something other than a trip six stories up - but by and large, most of us are going to climb into that metal box and push the 'six' button.
By the same token, people don't like their comfort being removed from them. Why do we not steal from work? Why don't we bash the head in of that annoying co-worker? We'd like to say it is because we're civilized, but a large part of it is because we fear the consequences for what we want to do. Think about a world with no consequences. Think how truly horrible people would act to one another if there were no consequences. If that doesn't work to get the point across, ask some of your friends who are in relationships if they would sleep with the "perfect" member of their desired sex if there was absolutely no chance of any consequences or their significant other finding out. Most people ask how they can be sure there are no consequences, flat out reject the scenario as possible, or at least sheepishly look at you and go "there's no way any of this comes back to haunt me at all?" if you don't believe me, try it yourself. It might not work on everyone, but I'd be willing to bet it does on the majority.
So, how do we use this? Well, like I said, people do things because it is either 1) the path of least resistance to a desired goal and/or 2) they fear the consequences of their desired action. The trick to opening someone up then is to make working with you the path of least resistance, and to overcome their fear of the consequences of working for you. How you do that is up to you, but personally I think a willing accomplice is better than someone you have to threaten into doing things. That is just me though, your mileage may vary. So, how do you open someone up? That is easy, find their price. Everyone has one, but not everyone's is money. Ideally, you want someone whose price is money though, it just makes things easier. Once you know their price, slowly pay it and recruit them to your side.
Then You've Gotta Socialize Them
By 'socialize' I mean the sociological definition of the word. This is more than just training, and more than just introducing them around to people, it is the entire package. You introduce them to, and teach them the role that they're going to be playing. You make them a part of the group, get them into position, and make sure they understand what that position means and how to do it. This is one of those areas where having the person be willing is good, because you can then take your time and teach them right. Which means less chance that they freak out and tip off a friend that something is going wrong.
Now, if you opened the person up, than they are likely already placed where you need them to be for the job. In this case, the socializing is in the illegal side of your operation. Teaching them what to look for, what to report, and when to do whatever it is you need them doing. You also want them to be able to act normal. If they're suddenly sweating bullets and acting all jittery, it could tip someone off after all.
No, not the inside man. The plan. With the first two parts done, all that is left to do is to pull the plan off and get away with whatever it is you were looking for. Afterwards you may actually want to execute the inside man as part of tying up loose ends, but you may also want to keep them. That depends entirely on how everything else has gone.
There are a few other ways to implement the inside man. But I'll save those for Thursday, when we talk about using this in your own games. For now, give some thought to the first two parts of this, as they're what is really important when using an inside man.