3 Keys To Taking On A Mastermind

One of the most challenging villains in fiction is the mastermind.  Knowing that they’re way smarter than you out of the gate creates more of a challenge than just the high hit points or armor of a big tough guy.  They always seem one step ahead and often become a long-running nemesis.

I started thinking about this again when watching an episode of the latest season of Longmire on Netflix. (Spoilers ahead!)  Chance Gilbert is the leader of a “family” of violent, anti-government extremists.  He cloaks his words in the rhetoric of liberty and freedom while arming to the teeth and being willing to kill to get his way.  His murder of a census worker sent him down a path of conflict with Sheriff Longmire.  Chance is highly intelligent, charismatic to the right audience, and well-educated.  He uses grey areas, cracks in existing laws, and nebulous arguments citing the founding fathers to resist paying taxes and obeying laws.  In the TV series, he kidnaps one of Longmire’s deputies and tortures her.  He is captured but masterminds his own escape leading to a manhunt and final showdown with the Sheriff.

Studying the Chance Gilbert example and reflecting on other examples in popular culture, I wanted to highlight the keys to a challenging mastermind villain.

1) Always Three Steps Ahead
Chasing a mastermind should be very frustrating.  Their plans are complex and seem to cover every contingency.  Heroes can end up running as fast as they can to find themselves just short of capturing the mastermind, saving the victim, or recovering the stolen object. Each failure of our heroes along this path should be a body blow, not a knockout.  They need to feel bested but not defeated.  The mastermind can strike at their weak spot, their secret vulnerabilities, yet always leave them wounded but alive. For example, a threatening message or even a bombing could reveal that the mastermind knows about their ultra-secret base, revealing a vulnerability.

There are several good examples of this in the Longmire-Gilbert plot line.  Gilbert makes his original escape from custody using a gun wrapped in plastic hidden in a toilet tank along with civilian clothes stashed nearby.  It took careful planning and the manipulation of helpers to set that up.  When Gilbert is on the run from the courthouse, he dons a gas mask and tuxedo as a disguise.  When the Sheriff follows him around a corner, Longmire finds dozens of people standing around in his exact outfit wearing gas masks; a perfect distraction while Gilbert gets away.  The decoy people are oblivious to what is really going on.  They had just answered a Craigslist ad with strange requirements that promised them a lucrative opportunity.

The mastermind also gains advantage by perverting assumptions.  A prison guard who is assumed to be doing his duty is actually aiding Gilbert by stashing the clothing, gas mask, and pistol.  If the mastermind can get enough leverage through knowledge or lies, they can turn all manner of law-abiding citizens into witting or unwitting allies.

Even our heroes can be twisted if the mastermind can put them in a paradoxical position.  The hero has to perform a criminal act to benefit the mastermind in order to save a captured ally or keep a sensitive matter secret.  Of course, once the hero does this, the mastermind is sure to capture evidence (video) of the hero aiding him as further leverage next time.  Often the hero must face personal loss (bodily harm, loss of reputation/job/standing) by resisting this leverage and making certain they capture the mastermind.

2) The Rare Error of Detail
Investigating a mastermind should be pretty frustrating as they are very detail-oriented and have planned for players’ expected reactions.  Still the mastermind needs to work with others to execute their plans, and those others are prone to making little mistakes.  These little errors are the sort that get an investigator hero’s radar up, teasing that something is wrong without pointing it out directly.

In Longmire, Gilbert requires the aid of a prison guard to make his escape work.  The guard is supposed to let him use the men’s room to change from his courtroom clothes back to his prison jumpsuit and sends him into a narrow stall.  Later, Longmire asks the guard why he didn’t put him in the handicapped stall which was much roomier.  This was enough to get the guard to start to crack and then give up what he knew of the plan (which mostly explained what already happened and not much of what was coming next).

If the heroes can detect some seemingly minor variation of procedure, they can follow that thread to uncover what happened.  Since few of us are current or former law enforcement agents, I would suggest that Gamemasters allow any officer of the law a roll to see if they think the other officers performed correctly.

3) Fatal Flaws
If a mastermind has no flaws, they are essentially unbeatable which is not fun for anyone.  The real way to take down a mastermind is by taking advantage of their weakness instead of struggling with their strength.  If their plans are unbeatable, change the game.  Tempt them with something that they obsess over, something that will get them to act without all the careful planning.

A typical fatal flaw for a mastermind is their arrogance born of belief in their own massive intellect.  They can be played by flattering that arrogance or potentially by challenging it, goading them into a style of conflict that favors our heroes or even just distracts them long enough for backup to arrive.

In Longmire, Chance Gilbert becomes obsessed with Deputy Vic Morelli.  He tortures her in an early episode but ends up getting arrested.  This gives her PTSD and a lingering fear of him.  He blames his failure all on her and makes elaborate plans to terrorize and kill her once he escapes.  His family writes scary messages on the side of her home and lurks around the hospital as she recovers from surgery.  This obsession makes his moves more predictable and forces him to act from emotion instead of logic.

Masterminds can be one of the most challenging villains to create for a Gamemaster but they can also be one of the most satisfying enemies for your players to eventually defeat. There's nothing like watching the bad guy get away time and again to amp up the players' desires to get him at last. I hope these ideas help you introduce a mastermind in your next game. 



Jim founded Dragonlaird Gaming Studios in 2005 as a channel for his original tabletop RPG work.  He’s an accomplished freelance writer with Knights of the Dinner Table Magazine (as a columnist) from Kenzerco, Margaret Weis Productions (Serenity, Battlestar Galactica, Cortex), and many others.  He published Savage Characters Volume 1 a couple years ago and has plans to release a series of Savage Adventures soon.  You can find his website at www.dragonlairdgaming.com.

Picture Reference: https://www.criminalelement.com/blogs/2014/07/longmire-season-3-episode-7-population-25-calls-for-help-craig-johnson-wyoming-edward-a-grainger

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