Free Will and Traitors in D&D


You lovingly crafted the end-dungeon boss encounter, carefully balancing his stats. You painted a miniature of his hideous drooling face, and spent hours at the table leading up to the climactic battle between the party and Sneery Evilton, mayor of Dicksberg. You even wrote some canned dialogue for him to recite to the party. Some pithy villainous barbs, like;

“We’re not so different, you and I.”


“Join me or die.”

And it’s at this moment, as the players clutch their d20’s in preparation to dispatch one of several Big Bads sprinkled throughout your game, this happens…

“Sure, I’ll join. What do I get in return?”

That’s right. One of the players has agreed to fall in line with the villain’s plans. And we’re not talking about a merc-hiring underboss from a cyberpunk game– someone just evil enough to hire a party of any-dirty-job thugs. We’re talking about Martin Shkreli face-punchable levels of evil. We’re talking damsels tied to traintracks, puppies ground into Orc-chow, Willy Wonka in a children’s burn ward. This is plain dag-nasty evil the player has agreed to sign on with, much to the party’s shock and horror.

How do you, the Dungeon Master, aka nerd enabler, deal with a turncoat? How do you let the party vent their frustrations without tempers boiling over? How do you re-unite the party in the face of a fracturing event? Here are a few tried-and-true tips…

1) Make the punishment for betrayal worse than the party’s desire for revenge.

There’s a story arc in Lord of the Rings: Return of the King wherein Pippin swears fealty to the fearful and corrupt steward, Denethor. In this instance Pippin is unable to see what the audience immediately grasps– that this is a bad man, cowardly, paranoid, and unworthy of Pippin’s service.

Before this moment Pippin has been nothing but a nuisance. He alerted the orcs to their presence in Moria by dropping junk down a well (on purpose, in the books). He picked up Palantir, the magic ball, and accidentally called the  attention of the Dark Lord’s eye. He’s a fool of a Took, a magnet for trouble, and a well-meaning idiot. Yet we all feel sorry for him when he’s trapped by the oath he hastily swears to Denithor. Hell, his plight is downright heart-wrenching.

If one of your player-characters manages to switch sides, betraying the party’s trust, this is how they should appear next time the party sees them. Beaten. Dejected. Mournful. It must be perfectly clear that joining the side of evil may come with all the perks promised by the big boss, but they will be used like the tool they are, with no regard to their happiness or well-being.

2) Have the player roleplay his turncoat reasoning.

hanshotfirst_01Han Solo shot first, and everyone not named George likes it that way. Han was a scoundrel, a smuggler, and a cheat. And no matter how many times he threatened to abandon the rebels we still cheer for him when he comes swooping in for the final battle.

If one of your players wants to turn traitor, make him make players understand why. It’s hard to stay mad at a scoundrel if they have a damn good reason. Maybe the evil empire has a better dental plan and the player has a daughter with cavities. Maybe the traitor is doing it for information, or leverage, or to double-cross the villain at a later date. Make them vocalize their reasoning to the group. This may save their character’s life later when they meet up again.

Or, if the player just wants the money or power, it will make everyone feel justified sprinkling his character with parmesan cheese and leaving him hog-tied in front of a dragon’s den.

3) Reward players for winning over the traitor.

terminatorgrinBetter still– the traitor explains why he want to abandon the party and join the dark side, and the players manage to argue him out of it. Rather than create a rift at the table this seems to be a bonding moment for the party. Now they know that they can use reason with each other when everything else has failed. Now they know that logical discourse and dialogue can be the last resort, not just wanton slaughter when they stop agreeing about who to side with.

The Green Ranger, Vegeta, Terminator– long is the list of villains who turned hero, and stayed awesome for it. Hell, I’ve heard plenty of internet arguments over why Boba Fett is actually a pretty cool guy despite all the evidence to the contrary. We like a bad boy, is all I’m saying…

Just remember to reward the party for winning the turncoat over. Extra experience for roleplay is my preferred method of reimbursement. You could also go with gold, magical items, or the reward of having another damage-dealer at their side and not cozied up with the Dark Lord.

4) Allow the party to let off steam.

beartrap01One final key point to remember: always allow a bit of friendly mischief between party members after a disagreement. Last week our monk, after disagreeing with the party twice, was proven right in his latest assessment of ‘lets not side with the black dragon.’

The party was immediately fractured. Over the course of about 20 minutes, however, it was revealed that the dark beastie wasn’t on the up-and-up, and his plans were more about wanton destruction than re-building the world. The monk who had stood his ground was proven in the right.

The party did not thank him. They simply admitted that they had been in error, and it could have happened to any money-hungry band of swindlers willing to make a deal with evil to get ahead. No harm, no foul.

In return the monk rolled a natural 20 on his sneak that night, and fouled all their rations with bird-droppings from a nearby collection of bird nests. So it was that the party who had recently bested a dragon came down with a furious case of the shits. Except for the monk, who was nothing but a turncoat not an hour before.

Featured image from D&D 4e Wiki.

Other images from Google Images.

Originally posted to


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