How To Play The Evil Mastermind

There has always existed a trend in party alignment. The majority of the party picks Good if they’re playing a classic D&D game. Evil, if they’re playing a dark campaign. Or Neutral if they can’t be bothered to invent reasons why they tied the mayor’s intestines to the sleigh before pushing it down the hill.

Then, every once in a blue moon, you get the player who thinks he can pull off a lawful evil character in the midst of a good party. Be it hubris, folly, or the belief that an evil alignment is a blank check for slaughter and theft; this misconception usually corrects itself when the party Paladin is forced to cut off his thieving hands.

If you’re going to play evil, I mean really evil, you owe it to yourself to do it right. Put aside the murdering thuggery, and focus on the bigger picture. Why settle for being a wallet-grabbing stickup man when you can aspire to the evil heights of Dr. No, Loki, or any other middle-aged British man.

So, because absolutely nobody asked for it, here are my tips for raising your standards from common criminal to Pure Dag-Nasty Evil.

Ignore Small Rewards


Pictured: +1 Boots of Shabbiness

Ever notice in movies how the evil mastermind will stop to rob an old lady because he’s short on cash? Or how Vader will halt his search for the rebel plans to loot the choked-out bodies at his boots? No? You don’t see Thanos going through Peter Parker’s dropped wallet? There’s a reason for that.

The villainous mastermind is above instant gratification.

It’s perfectly fine as the villain to accept bounty rewards or payment for a job well done. It’s your due, after all, even if that job was underhanded and loathsome. But the first and biggest mistake I see players make is to focus on the petty, instant rewards.

In the grand scheme of things, what’s a pouch of gold or a few credits? In fact, I’d recommend giving away gold or valuables to make yourself seem less threatening to the party. Because if you’re subtle and smart, your dedication to true evil will be rewarded with the trust of the people, which can be worth truckloads of gold and tons of influence. But only if you can…

Be Patient, Blend In

– Wiki

By now you’ve resisted the urge to murder the senile pawn-broker, and you’ve kept your puppy-kicking ways to yourself. Congratulations! Your ability to overlook quick gratification has allowed you to blend in with the party (so long as nobody casts Detect Evil)

So when do you finally reveal your true evil nature? When do you, the mastermind, unleash those pent-up bolts of lightning from your fingertips?

Not yet. Just wait.

Imagine you’re returning from a successful dungeon run, where the glittering jewel of Onk’Thur the Gaudy has been left in your possession, and the foolish party has given you first watch. Before you slip away into the night with the jewels, I want you to remember a radio station: WIIFM

In sales and marketing the acronym WIIFM refers to a short phrase: What’s In It For Me?

Sure, you might escape with the goods. But what then? Weeks later, after you’ve spent the cash and the party still wants your blood, how will you rejoin the group? How far will the gold really get you? What’s in it for you, in the long run? Instead, consider a more insidious tactic for glory and riches…

Drive the Party From The Back Seat

Pictured: Your Party.

— Google Images/Wiki

As the evil mastermind the people you’re adventuring with are, first and foremost, your personal minions. They just don’t know it yet.

By now you may be noticing a pattern in my advice. Almost every part of playing true evil relies in being as inconspicuous as possible, right up until the end. Think about the most villainous characters we know and love: Hannibal Lector, Dexter, Mr. Glass, Lex Luthor, Keyser Soze, Walter White, etc etc etc.

They don’t let their evil nature shine through until they’re at the zenith of their power, at which point they gleefully reveal their role in the group’s downfall. Even out-of-the-closet villains will take great pains to appear fair and righteous to their own faction. Someone in the galactic empire supported Palpatine after he went all dark-and-sinister, otherwise the Deathstar would have had a skeleton crew. And the aforementioned Loki spent years pretending to be Thor’s loyal brother before he unleashed his ill-gotten powers on Asgard.

But how do you keep party suspicion down?

Appear Outwardly Reasonable



Offer advice that sounds reasonable. Help solve the party’s problems. And appeal to their emotions. Your job, as the mastermind, is to nudge the party, not steer them. Let the Paladin or the Warrior take the lead. Wait until a suggestion is made to solve a current quest. And remember this phrase:

“I totally agree. But maybe we could…”

This sentence should end with a suggestion that both solves the problem facing the party and (more importantly) puts you in reach of more power and influence. Examples of this are:

a) Instead of seeking the source of a threat to the village and eliminating it (a tribe of goblin raiders, local bandits, etc) offer to construct defenses around the village, arm the villagers, train a militia to defend the town, and set up a permanent outpost. All for the good of the community, of course. And if you are put in a position of authority for the operation, you should humbly accept your new station…as mayor.


“Yup, much more satisfying than a bag of gold.”

b) Encourage the party to use miscommunication. Get them in the habit of holding back information from Lords and Ladies who send you on quests. Information is power, even if your Dungeon Master doesn’t intend it to be. Tiny details can change the scope of the game. If you “accidentally” misinform the local constable that a cult of C’Thulu, not Kor, is worshiping in the nearby swamps, who can blame you?

c) You’re offered a grand reward upon returning property/family to the local ruler. While the rest of the party loads up on weapons and gold from his coffers, politely decline all monetary reward. Instead, ask that you be granted asylum should you return to his lands. Or, arrange for free resurrection in his temple. An escape plan into friendly territory is priceless to the evil mastermind. Just ask any villain who’s ever stepped into an escape pod.

Have the “Big Picture” In Mind

Pictured: The Big Picture 2.0

— Star Wars Wiki

If these suggestions sound too small, too petty for an evil mastermind, I beg you to examine your favorite villain from pop culture. Unless they’re throwing around stadiums like Magneto, chances are they work in subtler ways than you think.

They lie. They push. They manipulate. But every one of their tiny deceptions, white lies, or miscommunications, adds up to one villainous goal. Because they have the Big Picture in mind.

Palpatine ended up with a galactic empire, while Dexter ended up with a mini-van. Why? Was Dexter too stupid? Too underprivileged? Too under-powered to do better? No. Their goals were simply different.

Dexter’s ultimate aim was to murder a string of dudes with a knife without getting caught. Not too big a stretch, really. Palpatine, on the other hand, wanted a planet-sized ball of murder and a coalition of worlds at his beck and call. He kept the Big Picture in mind. Sure, he died(ish) by being thrown down a ventilation shaft, but he got his murder-planet.

Every seemingly reasonable suggestion to the party, every white lie to the dungeon master, should be done with your Deathstar in mind. In the end you might be shut down by the DM before you can finally blow up Alderaan, but you’ll be that much more successful than the hapless thug who writes “Evil” for their alignment just so they can steal from peasants.

— Google Images

Unless this really is your end-goal. In which case, who am I to judge?

Published by jdplots

Author and mangler of plots.

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