A lot of people who sort of tangentially enjoy Dungeons and Dragons tend to play characters very destructively. In a lot of "standard" parties, the players can become very irritated at the troublemaker because if he ever becomes even slightly bored, he'll blurt out "I stab him!" in the middle of a delicate conversation, and everyone becomes cross.

But what if your whole party is a bunch of scoundrelous ne'er-do-wells? One of the hardest parts of DMing for a morally ambiguous or downright sinister party is the fact that it can become incredibly difficult to motivate them. I was having a discussion with one of our readers about my previous article in the series, and one of his remarks was that his party would not care about the children that the bad guy had trapped.

My first thought, of course, was what bastards. But D&D is and will always be about playing the character that you want to. Actions that do not directly affect the players in a neutral or evil-aligned game will not properly motivate them. Often times, you will need to restructure activities of the antagonist to be more offensive to the players, rather than a general morality. Allow me an example.

If we remember the example I gave in the article about Gardin, the villain escapes from your first combat encounter with him by threatening to harm a truckload of children. If you're worried about your players not being concerned with that, try this instead - as a wizard, he should have the capabilities within him to incapacitate at least one party member. Rather than continuing on to the next player, you can describe a scene where he scoops up the fallen friend and holds a dagger to his throat. Players will be reluctant to damn a member of their own team, and certainly will at least reconsider it under the fiery glare of the gamer next to them begging them not to let their character die.

But who are the bad guys, exactly?

In such a campaign, you'll have to take a second look at the sort of bad guys you field against your players. While it is perfectly fine to simply restructure motivations and run your original adventure, it pays to recognize the sort of thing that attracts them to these character types - it's not the evil, it's the chaos. They love causing mayhem. These sorts of people typically take a somewhat critical view of the law in real life, often holding poor opinions of policeman or politicians.

Having said that, the best way to inadvertently cause both good in your world and satisfy their need for social disruption is to vilify the authority. Perhaps set them against the corrupt guard and constable who are overtaxing the serfs. The players will be eager to "right the wrongs" of these authority figures in the most destructive way possible, often involving vandalism, assassination, and mayhem.

Blow Stuff Up

This is more of a general guideline than a specific piece of advice - if I haven't already stressed it enough, these players love to destroy. It is important to realize, however, that part of their satisfaction comes from 'cheating' and encounter or utilizing the environment against your enemies, solely for the sake of somehow disrupting you (the DM) and how they think you planned an encounter.

This sort of subconscious rebellion comes even when it is academically obvious that you set up the situation for them. Weak pillar supporting cannonballs above prison guards? All but the most oblivious players will recognize that the opportunity was specifically crafted for them, but they will still get the same satisfaction from it because you didn't specifically tell them you could. This technique works best when you mention structural weakness as part of a longer description of the room.

Why Fake Good Guys Make Good Bad Guys

The sort of overarching evil guys that you'll want to use in this party are the sort that are widely or supposedly perceived as good individuals, but are clearly not so. On an easy to understand level, the party will find it difficult to openly combat this sort of enemy because (unlike an evil dragon) they will constantly have the law and other do-gooders harrying them and making a direct strike impossible. On a deeper level, this sort of enemy will vindicate the feelings they harbor for people in positions of trust, and it will be rewarding to work towards taking one of them down. Plus, since they are technically fighting the law, the opportunities for mischief and disorder are rampant.

Some examples include:

• The Crusading Paladin: Everyone believes that he is a holy man leading the forces of good into battle against the wicked. Really, he is an insufferable zealot that harbors no mercy towards his enemies. A few strikes against friends of the party and his position as an enemy is set. He is very condescending, overwhelmingly sure of himself, and is completely immune to considering the idea that he might be overdoing it a bit. Examples include: Miko the Paladin (Order of the Stick), Goblin Slayer (Goblins), Kingpriest of Ishtar (Dragonlance), Young Spock (From the New Star Trek Movie, although he rectifies his ways)
  
• The Bad Cop: Generally regarded as a force against crime in their community, the bad cop/guard is actually buried in the underworld and uses his knowledge of the criminal activities for personal profit. He constantly blackmails those who he allows to continue committing crime, and uses the criminals for personal vendettas that he can't commit himself. He has either fabricated a crime against the party or has legitimately caught them in the act, and holds a compelling piece of evidence against them and is attempting to control them with it. Examples include: Officer Tenpenny (Grand Theft Auto: San Andreas), Detective Jimmy Shaker (The Movie "Ransom")
• The Dirty Politician/CEO: This guy got to where he is through money - pure, and simple, he is a business man and "public service" is his business. Almost certainly the head of - if not at least a major supporter - some criminal elements in the city, he comes in many varieties. Sometimes, he's a Duke that lets things slide as he slowly murders his way to the crown. Other times, it's a megacorporation CEO that uses the facade of the legitimate business to disguise his extensive organized crime operation. These sorts of people will simultainously earn a sort of grudging respect from the players, and present an excellent opportunity for them - their entire operation hinges on a positive public appearance. Things are kept tidy and out of the light. With a few surgical strikes, the PCs can ruin his entire life's work. Examples Include: Kingpin (Marvel Comics), Beckett (Pirates of the Caribbean), Commodus (Gladiator)

Or perhaps your villain is a mix of the types listed above, or another figure you players will find engaging.

Remember the Most Important Thing

...which is the fact that, as a DM, you are responsible for where the adventure goes and ultimately if the players are having fun. If you want to run a heroic adventure, then this article may not help you very much. But if your players just aren't that into being the paladins-of-the-week, then you might get a little more mileage out of running a campaign where all of your characters really, at heart, are...

..well...

Chaotic Neutral.