Wisdom of the Masters: Intelligent Villains

Wisdom of the Masters: Intelligent Villains

This article was first broadcast in Episode One Hundred Eighty Eight on 10th November 2021.

Lennon: Okay, so I don’t think Acererak needs gold…his house is already pretty impressive…
Ryu: What are you doing?
Lennon: Oh don’t bother; you can’t help me.
Ostron: Well I’m still not opening a portal to the nine hells for you so you may as well see what she’s got to offer.
Ryu: Standing right here guys.
Lennon: Fine. I’m trying to figure out how to DM and roleplay the big bad for my campaign. They’re supposed to be super intelligent and I’m…less so.
Ryu: Are you saying I’m too dumb to help?
Lennon: No, but I mean if you need to DM an evil person you just put on the hat and stop worrying about it.
Ryu” Well as much as I love her, KayDee sometimes is…less gentle with people than I’d prefer. I have to DM evil masterminds just as much as you do.
Ostron: So you have no problems with it?
Ryu: Oh, no I run into issues all the time.

One of the challenges of being a DM is similar to one that players can face with their characters. Someone who’s objectively not strong may be roleplaying a barbarian that can rip trees out of the ground but they don’t have to do that in person. On the other hand, a shy person playing an outgoing, friendly priest who comforts people all the time, or a person with no sense of humor playing a witty rogue often feel pressure to actually roleplay those aspects of their characters at the table, and that can be a challenge.

We’ll take this opportunity to remind everyone that’s not the way it’s supposed to work; If someone is roleplaying a master orator and they want to try to give a speech, that’s great. But the only thing that should matter for gameplay purposes is the die roll on their persuasion or performance; if they got a 20+ on their score it shouldn’t matter if they can actually give a motivational speech. Likewise everyone should be roleplaying like that rogue is the group’s personal Robin Williams even if the player themselves can’t tell a joke.

However, the DM arguably has a tougher challenge when it comes to evil masterminds. The same leeway should be given to the DM around speeches and so on, but that’s not the major problem; the mastermind is supposed to be able to outsmart and anticipate the heroes a lot of the time, certainly at least as long as the story needs them to. However, in reality the DM is one person and their ideas working against the minds of anywhere from three to six other people, some of whom may actually be more clever or intelligent than the DM. That’s unless you actually have a genius level evil psychopath for a DM in which case it’s very likely the quality of your D&D game should not be the first thing you’re worried about.

Assuming the DM is an average individual just trying to run the game, they are faced with the challenge of trying to come up with genius level plans and countermeasures without the benefit of the associated intelligence. So how are they supposed to deal with that?

Fortunately for DMs, there are ways to get around that, but be warned it does involve either extra preparation on your part or a lot of really clever improvisation, usually both.

As far as preparation goes, the easiest way to conceive an evil plan’s details if you can’t think of them yourself is theft. I mean, it’s an evil plan, you may as well start with deviant behavior out of the gate. Using ideas from other people is a tried and true trick for DMs everywhere, but with large evil figures you sometimes need to take it to the next level. Steal traps and dungeons and ambush scenarios from D&D resources sure, but also be willing to steal larger plans and ideas. If you want medieval family intrigue, there are numerous epic fantasy stories with plots around angry illegitimate children, conniving step- and half-siblings, or just rival members of the same family.

If you need a conquering or takeover plot and don’t want to go the route of “they just have thousands and thousands of troops,” look at figures like Saruman or even Palpatine from Star Wars. It requires looking into the plotting and some of the backstory more than with a casual read-through, but both of them worked fairly subtly for years and played different factions against one another before finally coming out as full evil masterminds.

If you can’t think of any good fictional sources for whatever plot you want to run, or if you’re worried you won’t be able to disguise it enough that your players won’t recognize it immediately, crack open a history book. Takeovers, betrayals, coups, and complex plotting, evil and otherwise, have literally been going on for millennia. If you need inspiration for how a conniving mastermind would get themselves power, you can start with things like the history of the Caesars in Rome, The Tudors or the Medici families in Europe, the communist revolutions in China or Russia, or the Shogunate period in Japan, and that’s just the tip of the iceberg. You can even look into non-political things like the mobsters of the 1920s, the robber-barons of the industrial revolution, or activities of groups like the Yakuza; even though they weren’t concerned with political power, per se, they still used underhanded methods to get themselves some kind of power.

One cautionary note there, however; if you’re looking at real history it’s usually best to start at least 100 years ago or more and work backwards for inspiration. Descriptions of history more recent than that can still be tainted by emotional interpretations based on modern politics and may have things omitted or glossed over for various reasons. In the United States, for example, depending on what sources you look at you’re still going to get wildly different descriptions of the motivations for the American Civil War.

But let’s say you’ve found your inspiration for the evil plan. You’ve got the plan all worked out, pieces are in place, blackmail and extortion is in process, your villain is on their way to dominance. Enter the heroes. Now you have a decision to make, and that will inform what you need to prepare for; are the heroes going to be aware of the villain’s involvement or not?

If this is a Sauron or Strahd situation where everyone knows who the villain is and where they are and the whole point is just to get to them then you don’t need to worry about most of the rest of this. However if you’re either doing a recurring villain scenario or a grand betrayal situation, you have more work to do.

We’ll start with the grand betrayal. This is when the heroes will run into the villain multiple times without knowing that they’re actually the villain. Palpatine from the prequel Star Wars media is a prime example of this. What you need to prep for in this case is ways the villain can be running things and setting themselves up for power, but they’re not obvious about it. Some of your research into the larger plot may help you figure out ways your villain could hide their involvement, be it a false persona or secret proxy agents or whatever. The key is that they shouldn’t publicly be involved.

The benefit to this approach is you don’t have to come up with how they’re running their evil scheme right away; the heroes will start by dealing with the obvious issues and low-level brutes carrying out menial tasks. It’s only once they get into it they’ll start looking for the mastermind. However you do have to figure out how they’re involved eventually because the heroes will need to start finding clues that point back to the schemer.

On the other hand, you can go with the recurring villain approach. In that scenario, the villain may be hidden for a little while but their identity will be revealed relatively quickly. At that point you have the next challenge; keeping your villain alive.

Getting into combat with the heroes is a quick way for someone to die; either the evil mastermind will die because heroes are annoyingly efficient at killing any single target when they put their mind to it, or one of the characters is going to die because the villain is a high enough level to shrug off the heroes’ attacks, which means their own attacks are going to level the competition.

The answer to that is escape routes and traps. James Bond villains, for example, almost always encounter the titular hero a few times before any sort of final confrontation takes place, and they always end up trapping Bond in some sort of dire situation or sending a wave of minions to tie him up and stall pursuit. Eventually regardless of how your villain started, you’ll need to figure out how they’re going to escape confrontation with the heroes. Fortunately there are a lot of options in most D&D games; teleport is a wonderful spell, for example, but what do you do if someone has a counterspell? Or what if they beat the initiative and manage to hold person them before any casting or movement can occur?

So where a real evil mastermind would need to think up counters on the fly, you as the DM have the advantage of omniscience. You know what all the heroes are capable of doing, so you can prepare counters for them in advance. Having two or so counters for each character’s signature moves is probably good enough to give your villain time to escape, and you don’t have to worry about burning legendary saves or similar one-off solutions because the guy isn’t in the fight for the long haul.

Those are some specific examples that can help but in general the best way to improve your villain’s intelligence is they way they do it with computer networks; get more nodes involved. Find a Discord group (such as the one that Heores Rise has), talk to D&D players from your friendly local gaming store, or even post on Reddit if you’re desperate and crowdsource the solution. Put up the general scenario or the specifics if you have them and ask people to punch holes in the plan and find obvious weaknesses you may be blind to but the villain would have anticipated. You’re trying to imitate someone who has vastly more intelligence than you do as an individual, so don’t feel guilty or inadequate if you need more minds on the problem.

Which is great if you plan in advance but what if something goes wrong in the moment and the players have a burst of creative imagination that shortcuts all your ideas? In some cases you should let them have it; just let the villain get their comeuppance early and promote someone else to fill their spot. Or make them not actually the villain. However if you really want to keep that specific person alive, the best thing to do is simply fake it and retcon. Get them out of there and think of a reason they were able to vanish later. Again, you can crowdsource the solution after the fact, but another thing that a lot of DMs have taken advantage of is having their players give them the answer; the players are bound to speculate about how the villain got away, so if you’re really strapped for ideas you can just listen to their theories and then pick whichever one you like best.

As we mentioned when this first started, all of this involves work. Looking up information and crowdsourcing solutions aren’t usually things that can be accomplished with a Sly Flourish 20-minute prep session, and if you want the villain to be both intelligent and believable it’s worth it to put in the time so they can seem to have the smarts and anticipation they’re supposed to.

One final thing to remember in this whole endeavor is that you aren’t trying to beat the players. You want to create a repeating, believable villain with above average intelligence, but ultimately the idea is that the players should be able to win. Make sure to leave them a way to do that. At first when you need the villain to survive you should be closing off all the loopholes, but later on you want to make sure you give the players a path to victory. Hopefully if you do that, the players will end up greatly satisfied at finally taking down the villain that’s been outsmarting them the whole time.


Lennon: Okay, that gives me some better ideas.
Ostron: That’s the point, isn’t it?
Lennon: So wait, the KillerDM really isn’t helpful with those kinds of things?
Ryu: I mean…okay don’t tell her I said this but KayDee isn’t a whole lot smarter than me, she just has more…stuff. I mean when she finds out someone’s smarter than she is she just…kills them.
Lennon: Well, that doesn’t make sense because she kills Ostron all the time but she barely ever…hey! Wait a minute!
Ostron: Scrying pool?
Ryu: Scrying pool.
Lennon: Hang on! Guys! Hey, the Killer DM is not smarter than me!