The Mastermind is an incredibly popular type of character in pretty much every format of storytelling that is out there. Really, it isn't surprising either, a character that takes complete control of the situation by reading the situation, the people involved in it, and making surprisingly accurate predictions about how things are going to play out, and how to manipulate those events to make them come out in the character's favor.
This type is depicted in a number of ways; the 'planner' for a heist, the legendary strategist, the chess master, the poker player. All of these are examples of ways that the Mastermind gets played out, and that isn't even including all the times that it is simply called what it is, a Mastermind. So why is it that such a popular character type in works of fiction is such a hard thing to pull off in a game? Lets start by looking at what a Mastermind is.
What makes a Mastermind?
A Mastermind character is pretty much the ultimate expression of brains over brawn. They are very rarely combat capable, and when they are they are never the most or even second most capable character on the team (to be a true Mastermind, there needs to be a 'team' of some sort). Instead they make up for a lack of physical ability on their part with an excess of mental ability. Making plans that very likely have back-ups and contingencies all the way from A to ZZZ. They use these plans, and the resources available to them (read: other team members) to make something significantly more than the sum of its parts and pull of truly amazing stunts and missions in a way that makes them appear significantly easier than they actually are.
When confronted with a setback, and there isn't a contingency already in place for that set back, the Mastermind is only out of the game for a short while before they're able to plan for the new set back and the new variables brought into play. The end result being a daring "How do they get out of this one?" with a satisfying bit of intrigue and drama before everything plays out exactly as the Mastermind planned.
How does the Mastermind Work?
Now I am not talking about what the Mastermind does, but how it works. Essentially, how the audience sees what the Mastermind is doing, and in a lot of ways a Mastermind character is played out much like a musician. The three stages are a bit different, but it does essentially follow the formula of a magic trick.
Step 1: The Set Up
This is where things start to go wrong, or at least where the challenge is set. There is an objective, and acquiring the objective is going to be next to impossible. The security makes Fort Knox look like a joke (it is amazing how often the security makes Fort Knox look like a joke btw), the guards are all ex-Special Forces, possibly even high level Special Forces like Delta or Mussad. The network is of course a stand-alone with no outside access and probably 3 terrabyte encryption to boot. No one can get in, no one. Well, no one aside from our Mastermind and his band of people.
Step 2: The Execution
Here we have the plan going into effect. You see the individual team members doing their jobs and getting through. Everything goes according to plan, because the plan accounts for all possible contingencies and other such things. Generally though, this is shown to not be the case, and something will happen that throws everything off, causing the whole plan to fail. Only by failing, everything succeeds and works out nicely for the team involved. Which is confusing until you hit...
Step 3: The Reveal
Here, finally in the end, we are shown how the whole thing was pulled off. The parts of the plan that weren't given to the audience in order to set up the drama when things go wrong. The true intention behind steps that we were shown, as well as other little things that show just how the Mastermind not only predicted the coming trouble, but preempted it and made it work for them instead of against them. This is the key difference to a Mastermind and a Magic trick, because you shouldn't be seeing how a magic trick was done, but a Mastermind's work isn't fun until you see how it all played out.
So why is this hard in Games?
The reason this is hard to do in games is specifically because of the Reveal. You don't get the same level of fun out of the reveal because everyone already knows everything that is going on, and presumably why. Also, there is no challenge when the plan goes as smoothly as it does for Masterminds, which is the reason for the reveal in the first place. By keeping the audience in the dark you cause the drama to happen, and then show them how it was done. In an RPG though the Audience is the characters, so they already know that and the drama goes way down. When you fix that by actually introducing elements that weren't planned for, the Mastermind character is ruined a little bit because they didn't foresee the eventuality that ruined their plan.
Now, I'm not saying that it can't be done. Just that it is very hard. The GM's job is to challenge PCs, and that would include the Mastermind. To do the Mastermind's job though that player needs info. A LOT of information, like a ridiculous amount of mundane information that will bore everyone else. They also need time to go over things and plan things out with the GM. This planning session can (and should) happen out of game, and die rolls should be involved to help the player come up with complications that could come up and ways to plan around it.
Aside from that, you need a very specific kind of player for a Mastermind. Someone who can think on their feet. After all, the GM's job is to challenge the PCs and no matter how good a planning session is most people can't cover every contingency, and in some cases the GM will still have to throw a monkey wrench in the plans. At that point, the Player needs to be able to think on their feet, adapting plans and goals to deal with the new thing on the fly and pull everything off. It can work, it is just a lot of work. Possibly more work than it is actually worth in the long run for a table top RPG.
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