Chessmasters are bad villains.

Another in the ever increasing fun "letters Home" series. In this first edition of "villain types" we will look at what makes a Chessmaster a horrible villain.

Yes but what is a chessmaster? TV Tropes says: Chessmasters tug at their strings of influence, patiently move their pieces into places that often seem harmless or pointless (until the trap is closed), and get innocent dupes to do all the heavy lifting. The best will also have layers upon layers of misdirection and backup plans in case some unexpected hero appears to gum up the works. They take the (very!) indirect route in order to snake through holes in their opponents' defenses without a trace... assuming they can refrain from boasting of their cleverness near the hero.

At first glance it looks like a chessmaster is the cookie from which our villain cookie cutters are wrought. But lets not get too hasty. Casual players will be at a very large disadvantage against this type of villain. Plots within plots within faints are a sure fire way to lose a player that just wants to hang out and kill some orclings (half orc halfling (wow my brain hurts after that joke)). As well, casual players are not known for digging too deep into the plot, and to pull off a truly epic chessmater you will devote sleepless night after sleepless night bent about a chessboard debating the wither to's and the why for's. none of us like when players avoid our clever little plots, especially when we pour a lot of work into it.

That leads to the next point, the planning. if you have a group that has the foresight and cunning to deal with a chessmaster they might well be chessmasters in their own right. In literature most chessmasters will only duel one other chessmaster; in a role playing game your chessmaster will fight a cadre of chessmasters working in tandem. To build up the faints and subplots that are complex enough that the players don't spot the connections right away, but not so complex that they never notice (thus wasting all that work) takes a large measure of knowing your players. Not just what they like or their limits, but how they think. A task that has an entire branch in the scientific world devoted to, that you get to do faster and more accurately then science-y types. If you fail at all in one of the planning steps the whole villain crashes down.

If all thats not bad enough, a chessmaster is a far more cunning quarry then a simple blackguard. More likely then not the players will have to trick the chessmaster using a feint to draw him out, and he will likely have a contingency prepared. After the first failed attempt the villain will now be on his guard, expecting such a faint again, and prepare more "just in case" moves.

Thats not to say you can't dumb down a chessmaster, or not add that one last sub-plot plot. A "low level" Chessmaster might be just what you need to test the waters. If the players love it and work well as pawns, go ahead and toss in the real deal. I promise players will spread the tale of the faceless villain for years to come.