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D&D: Five ‘Heroes’ That Aren’t Good

5 Minute Read
Jan 22 2020

Is the enemy of your enemy truly your friend? Here are five characters doing the right thing for the questionable reasons.

Everyone loves drama. And not just in the ‘Jaeden didn’t like my tweet but he retweeted Brylor AND Khaleesi’s latest TikTok’ kinda way, or even necessarily in the ‘my uncle killed my father, probably maybe, and now I’m not sure if I’m seeing my dad’s ghost or am crazy? so I should kill everyone’ kinda way. But rather we love the feeling of conflicting emotions. Of knowing something that our characters don’t and pressing on ahead into a sticky situation.

And one of the best ways to generate conflicting tension is to have a conflict where you don’t necessarily hate the people on the other side. Heck, they might even be on the same side, but the conflict comes from within, as we talked about in our guide to villains that aren’t evil. The other side of the coin, though, is to have friends that make you sit back and wonder: are we the baddies?

Or, if you’re not looking for the twisty kind of drama, you could get those exciting moments when the heroes and someone who was nominally the villain team up to take on an even greater evil, and suddenly you’re fighting side-by-side or back-to-back with the dark wizard you spent the first half of the game trying to take out once you finally got past the millennial fair mini-games.

You can get a lot of milage for dramatic or comedic effect out of having people that might be villains in another story fight alongside the PCs. These are the ruthless mercenaries who have been paid enough to fight on the side of the angels, this time. Or they’re the evil wizards who will brook no rival to their utter dominance; or even just a bounty hunter who only cares about finding their targets, and doesn’t much care what they’ve done.

Here are five ‘heroic allies’ that aren’t good, but are still perfect allies for adventurers of any alignment.


The Assassin

Kalas Vinsmire is a foppish noble who also happens to be one of the deadliest assassins. Part of a guild of hired killers who specialize in eliminating targets for politically ambitious courtiers, Vinsmire has adopted the moniker of ‘The Adder’ when out in the field. Vinsmire might have tried killing the PCs in the past, or may come to fight them in the future–but is an excellent ally when needing to secure entry into a formal event that the wandering hobos of a typical adventuring party might not be able to get into. Vinsmire might offer to help them sneak in, or help in a fight–but is always working towards his own end, which typically is killing a particular target.

For some interesting conflicts, it can be someone that the PCs might not necessarily want dead or are trying to keep safe, once the party has concluded their business with the target NPC. Vinsmire is nothing if not pragmatic, and knows better than to stick around in a fight where he’s outmatched.

The Bandit Queen

I am a huge fan of villains who act in their own best interest, especially when that best interest demands that they help the adventuring party whether they like it or not.

Oleanna Kuo is a bandit queen. She is the terror of a local stretch of difficult terrain, be it desert, harsh forests, or wintry wastes–but when the adventurers come along and look to investigate the monsters emerging from the strange ruins, Kuo offers to help them. Or rather, Kuo sends some of her bandits to die in the ruins to see if there’s any treasure worth taking, and if they can kill any monsters, even better.

Once the prospect of treasure or keeping monsters at bay might draw Kuo out of her bandit fortress to come and help the PCs while also building her own bandit empire.


The Mercenary

Baldrick Rowan is the hard-nosed captain of the black blades mercenary company. The black blades work for whoever pays the most for them, and they don’t much care about the political ideology of who they’re fighting for. They have fought to put tyrants on the throne, and have helped the poor overthrow their despotic masters, only to turn around and conquer the city when a distant Warlord set their sights on the city.

When the party takes on an assignment to fight a particularly difficult foe, Rowan and the Black Blades might show up as people fighting against the same foe. It’s the perfect chance to play up a threat that will come in the future–or even to show how the mercenaries can be dealt with (by buying them off) should the PCs find themselves on the wrong end of the Black Blades.

The Cultist

For best results, try and mix in a villainous ally working towards an end that’s roughly beneficial immediately but that might carry long term consequences. Consider Flennara Niral, a yuan-ti cultist who is an expert in all sorts of ancient magical secrets. She might help the party destroy a relic, or magical ward, but the PCs know that every time they let her help they are furthering the cause of the serpent god she follows, and it’s only a matter of time before their dark ambitions come to fruition–but in the meantime, Niral is just so useful.

The Hunter

Klarn is a hunter. Klarn hunts whatever Klarn has been told to hunt–and Klarn always finds them, whatever it takes. Sometimes Klarn brings them back alive, sometimes Klarn just has to bring back a trophy. Klarn hunts friends and Klarn hunts foes. Here’s a great ally to have early on, as the PCs gain Klarn’s help in catching a powerful monster, or hunting down an illusive villain–especially if one day, Klarn shows up to hunt them.

Grab one of these allies the next time you want to give the PCs a helping hand, but not necessarily with the best of intentions.

Happy Adventuring!


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