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, because they can’t be bothered post-murder to invent reasons why the mayor of Whoville had to have his intestines tied to the sleigh before it was pushed down the hill.

Then, every once in a blue moon, you get the player who thinks he can pull off an evil character in the midst of a good group. 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 for no other reason than to placate his own good-aligned god.

I find, without exception, players pick evil in Pathfinder or Dungeons and Dragons not because they want to experience the evilgasm most Demon Overlords or EA CEOs feel on the daily. But because they don’t want the penalties that come with murder-looting anyone who dresses better than a hobo.

Hobos_02“Nope. I’d still bludgeon him for his stick-bag.”

I grant that murderous thugs with tear-drop tattoos under their eyes are undoubtedly evil. Or victims of a cruel prank at Tattoo College. But if you’re going to play evil, and I mean really evil, you owe it to yourself to do it right. Why settle for a wallet-grabbing stickup man when you can aspire to the evil heights of Dr. No, Loki, or Goldfinger… or really any middle-aged British man.

So, because absolutely nobody asked for it, here are 5 tips for raising your standards from Common Criminal to pants-shittingly evil.

1) Ignore Small Rewards

Fortunes_of_a_Street_WaifPictured: +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? There’s a reason for this.

The villainous mastermind is above instant gratification.

It’s perfectly fine as the villain to accept bounty rewards, taxes, or laurels for a job well done. It’s his (or her) due to receive payment for a job, even if that job was a tad underhanded or required a healthy amount of intimidation. But the first and biggest mistake I see players make is to focus on the quick, small rewards.

In the grand scheme of things, what’s a pouch of gold or a few credits? If you’re subtle and smart, your dedication to true evil will be rewarded with the trust of the party, which can be worth truckloads of gold and tons of influence. But only if you can…

Be Patient, Blend In


— (ad for Livepoker)

“I take 20 for my disguise check…”

So, you’ve resisted the urge to bash the skull of the senile pawn-broker, and have 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 in your direction)

Now, is it finally time to reveal your true nature? To unleash ropes of lightning from your fingers while your features twist into the wizened creases of a maniacal emperor mad before his time?

Meh, close enough.

There may be profit in revealing your dastardly ways halfway through the campaign. You may be 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 make your escape to Cancun for Mai-Thais and cheap prostitutes, 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 jewel. But then what? Weeks later, after you’ve spent the cash and the party still wants your blood, how will you rejoin them? 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)


— Google Images

Pictured: Your Party.

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 didn’t let their evil nature shine through until they were at the zenith of their power, at which point they (gleefully) revealed their role in the hero’s downfall. Even out-of-the-closet villains will take great pains to appear fair or righteous to their own faction. Someone in the galactic empire supported Palpatine after he went all dark-and-sinister, otherwise the Deathstar would have a skeleton crew. And the aforementioned Loki spent years pretending to be Thor’s loyal brother before unleashing 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 dilemmas. And appeal to their emotions. Your job as the mastermind is to nudge the party, not drive 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 in front of 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) 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.

holy_grail_cleese_01“Yup, much more satisfying than a bag of gold.”

b) Encourage the party to use miscommunication. Get them in the habit of holding back facts from Lords and Patrons 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 slip and tell 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 from his armory and gold from the 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


— Star Wars Wiki

Pictured: The Big Picture (2.0)

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? Did Palpatine begin life with a dozen Dark-Jedi to do his bidding? No. Their goals were simply different.

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

Every seemingly reasonable suggestion to the party, every white lie to the dungeon master, and every tiny contribution to the main quest should be done with your Deathstar in mind. In the end you might be shut down by the dungeon master before you can finally don your evil crown, but you’ll be that much more successful than the hapless thug who puts “Evil” for their alignment so they can steal from peasants without an alignment shift.

-- Google Images

— Google Images

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


4 thoughts on “How To Play the Evil Mastermind

  1. One almost gets the feeling you speak from experience Joe. But I’ve got a question:
    What if I see something that I wanna take and it belongs to someone else?

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