Dungeons & Dragons Online

Making Villains Matter: Dragon Heist


A couple of weeks ago I posted a guide to making your villains an up-front, top-shelf threat that the players really get to know long before initiative is called in the set piece battle. If you haven't read that, it's okay. You'll pick it up by context.

Essentially, the goal is to make your villains a present force in the campaign world, visually and influentially, as soon as you possibly can. I just started a second campaign in Frostmaiden and the players saw Auril up close session one. My players are itching to send her to Cania.

I proposed a general system of escalating encounters with increasing stakes as the players bump into the villain's plans. The villain starts as a figure of renown – either as a source of fear, adoration, respect, or even goodwill – and eventually their social protections fray as the players lead them deeper into conflict with their badder nature. Players are the catalysts for your villains! Without opposition, a villain's plot is really just someone's typical Sunday afternoon. It might be evil, but a plot is only a plot once it faces adversity. Players are the adversity.

Making Waterdeep Work

I have a whole writeup that I'm going to link at the end of this post. It's essentially my fever-dream midnight madness version of Dragon Heist, which I believe has the most potential out of the published adventures for this kind of socially-restricted conflict between villain and players. Except, we're going with villains, plural.

The first thing I outlined in my notes is my attempt to get the tone of Waterdeep right. As it's presented in the book, it's a vanilla high fantasy city with some really cool stuff tucked into the Enchiridion. Most of that cool stuff is pretty well tucked away, however, and you absolutely must tease out the best setting information for yourself.

My initial impression of Waterdeep is that it works better as D&D Gotham. Simply by shifting your frame of reference and looking at Dragon Heist as a Gotham-esque urban crawl, you get a lot of the feel of the game down. Moody atmosphere, how the cops – I called the city watch the WDPD – and baddies behave, and how your big villains interact with the setting can all benefit greatly by centering Waterdeep squarely in that genre-space.

The second thing to do is to have all the villains in your game. The way it's written, Dragon Heist really wants you to use one villain, then run the adventure again with another, and another… But the game is most interesting when all the villains are used (except for Jarlaxle, I'll get to why in a bit).

The third and most important thing you can do off the bat is to give your players Trollskull from session one. It's a must that the players have a home base in this kind of game. Every hero has a crash pad. Batman has his cave, Daredevil an apartment, and Catwoman the abandoned mansions of Gotham's wealthy. Plus, as you'll see, it can be used as motivation to draw your players into the madness.

What to Change, What to Keep


These most important elements of an urban game must remain. However, we can do a whole lot better than simply using the NPCs the way they're presented in the book. So, I present to you a refined dramatis personae for the whole of Dragon Heist (or at least the ones who are important and who've been altered).

  • Volo – A police informant and once-upon-a-time fixer for the Zhentarim gang. He gives your players their initial quests and currently works directly under the sole supervision of Sergeant Cromley.
  • Sergeant Saeth Cromley – WDPD's own Commissioner Gordon. He's the one on the roof surveying the bleak and steamy back alleys of a city fraught with crime and vice. He's the one trying to navigate a corrupt police department and Waterdeep's entrenched political corruption. He's your party's benefactor.
  • Manshoon – The Don of the Zhentarim crime family. This guy is Kingpin. He's got the docks, the warehouses, the night clubs, the gambling rings, the races, and bootleg liquor. He runs the low-level gangs of Waterdeep. Somebody needs protection, they come to the Don. He's untouchable.
  • The Cassalanters – They don't change much, but the way in which they're presented to your players does. They are only revealed as villains later in the course of the adventure, as befits a cult of devil-worshipping nobles. Before that, they can seem like wealthy benefactors vested in the future of Waterdeep. They are loved by the common folk. Think a celebrity power couple off the silver screen in the golden age of cinema.
  • Xanathar – A secret villain. Pulling the high-level government strings. He has the Open Lord of Waterdeep mindslaved with an intellect devourer and he plans to take control of every chief position in Waterdeep's government, no matter how long it takes. The players run afoul of him when they start dabbling in other villains' plots.
  • The Black Viper – Secretly Manshoon's daughter (except to Manshoon, he knows her identity). She is a potential ally to the players, but she only wants one thing: To stop her father. She is the Batman of Waterdeep, but might come to view the players as valuable allies if they prove useful or effective. Otherwise, she is instrumental in establishing your players as "players" in the game of intrigue happening within Waterdeep.

The McGuffin

The Stone of Golorr is incredibly important because without it, the Vault cannot be opened. Only the Stone knows which keys are necessary to open the Vault. However, we want our players to have a reason to want the Stone, and a great way to do this is to show them the Vault in session one. The players get their first job from Volo and go to an abandoned tower, where they run into a group of Zhentarim goons searching for the Black Viper. After the Zhents are dealt with, have the Black Viper show the players the Vault entrance beneath the tower and take off.

Boom! Vested interest. Now the players not only know where the Vault is, they wonder what's behind it and what the Black Viper wants from it. Why were the Zhents following her? They also have incredibly useful information. Only the Black Viper, the players, and Xanathar know of the Vault's location, which means Manshoon and the Cassalanters have a reason not to kill your players in a fight.

The Stone eventually ends up in the Cassalanter family mausoleum in the City of the Dead, where it stays until a villain or the party finds it.


This chapter is a doozy. I go into it in the write-up, but suffice it to say that shoehorning the plot into the players' lives by having an NPC they've never met try to bring them the Stone of Golorr because he thinks that's what Dagult Neverember would do…? Lazy writing.

Instead, we're going to shoehorn it in by bringing the players to the Stone. We do that by revamping this chapter quite a bit, but the main thing is that the Zhents have the stone in one of their secret rum distilleries on Trollskull alley, beneath a bakery (which in my games replaces the private investigator). The Xannies show up to take it back from the Zhents who stole it from Xanathar, and chaos ensues. In the commotion, a construct sent by the Cassalanters throws a fireball into a bakery full of rum and the explosion rocks the block.

Now your players are interested. The best sequence of events is to have the players inside the bakery when it blows. Have them hear the Xannies and Zhents fighting, give them a chance to rush in and start mopping up, then BOOM! Hit 'em with a fireball and the floor caves in to the sewers. Now your players have to fight their way through the sewers alongside the Zhent double agent Urstul Floxin, who's in cahoots with the Gralhunds and, by extension, the Cassalanters.

A Wild Villain Appears…

The above is a condensed version of my write-up. If you don't read that, using what's above can help your Dragon Heist feel a little bit more like a sinister game of cloak and dagger. It pulls the narrative net a little tighter, eliminating those pesky plot holes like "Why did a random gnome decide to bring us the stone?" and "How come Xanathar forgot where the Vault is even though he had the Stone of Golorr for like a month?"

The final bit I have for you is a sample of the villainous interactions between the players and one of the other major players. I'll be using Manshoon because I really like him as the baseline villain. Everyone in Waterdeep knows he's a bad guy and a crime family boss, but he's so insulated by his bribery and intimidation that he can effectively do whatever he wants. Even prison isn't prison to this guy. He just buys the whole prison staff off and suddenly he's in a fortified encampment within the city limits, from where he can maneuver his pieces in the heist. Always assume he has the money and muscle to buy people off.

With that in mind, Manshoon is looking for the Vault for the gold within, sure, but also for the influence it represents over the Waterdhavian people and government. He believes he can buy Dagult with the gold, too, and having a fellow criminal lord under his thumb is just the sort of thing that gets Manshoon motivated.

Finally, keep in mind that the Manshoon the players interact with throughout this entire adventure is a clone. The real Manshoon is always in his secret tower lair within a demiplane. If the players thwart "Manshoon," the city restructures but he keeps pulling the strings from the shadows until the time is right to strike.

  1. The first encounter. The players see the don out on the town. He’s accompanied by an appropriately handsome companion or two and a retinue of guys packing serious steel. They can be out for a night at the theatre, enjoying a meal in a fine restaurant, or at a club enjoying the visual enchantments of dancers and performers. The players would be suicidal to do anything to the infamous mob boss at this point, and they don’t even register on Manshoon’s radar. He’s completely safe in his city, and they’re nobodies.
  2. The second encounter. The players have completed the first job from Volo, which led them into conflict with the Zhents searching for Esvele/ the Black Viper. Manshoon might become aware of them, in which case he invites them to have dinner with him at a really fancy bar in Waterdeep’s Sea Ward. The invitation is delivered by a handful of tough-looking Zhents whose presence makes it clear the invitation isn’t one you can refuse. It’s at this dinner that Manshoon inquires to the players’ intentions within the city, whether or not he can “trust them,” and insinuates that working for him would be a far fairer fate than meeting their unfortunate end. Pull out all of your best mobster one-liner’s here. Manshoon doesn’t make any moves to kill the players, but if they refuse, they are ambushed later and taught a painful lesson to the tune of being beaten to a pulp and left unconscious in the gutter. Nobody says no to Don ‘Shoon.
  3. The third encounter. After the events of Chapter Three, Fireball! the Zhentarim become embroiled in a gang war with the Xannies, and Manshoon can’t help but become aware that the players live awful close to the bakery where the Stone of Golorr was being kept. A few nights after the explosion, the players awaken in the middle of the night to the sound of things breaking in the taproom of Trollskull Manor. When they enter the ground floor, through a window they see shadowy figures darting into the shadows in the alleyway. The taproom has been trashed and a goat’s head has been dumped on the floor along with a note that reads, “Manshoon sends his regards.” This is a threat and a reminder of who’s in charge.
  4. The fourth encounter. Run this encounter with Manshoon only if he doesn’t have the Stone of Golorr or if the players have actively continued to oppose him. Otherwise, he’s more concerned with the other factions in Waterdeep. Manshoon’s men arrive at Trollskull Manor or find the players in town. They’re asked to get into a coach and are driven to a theatre where Manshoon is viewing one of the productions from p.74-76. He sits in his private box and smokes a cigar while the performance takes place. The players are offered fine rum or whisky and cigars, and Manshoon speaks to them in hushed tones. For a while, it seems like idle banter and small talk. Eventually, he cuts to the chase… But only with appropriate mobster flair. — (For this encounter, I used the performance on p.76, which mirrors the backstory of Strahd. At the point where the performance depicts Tatyana’s suicide, Manshoon laments the pride and unwillingness of Tatyana to do what was “smart,” then delivers his ultimatum: The players can tell Manshoon where the Vault is located, or they can meet a similar fate. If the players refuse, Manshoon sighs and has his guys take the players up to the roof of the theatre. He doesn’t accompany them and is seen from the rooftop departing the theatre as his lackies are preparing the party’s “accident.” They already have bodies of doppelgangers on the roof, perfect for pinning the affair on the Xannies.)
  5. The final encounter. This is when Manshoon can snap and show the players, and the city, his bad side. This only happens if and when the players have thoroughly obstructed his plot to recover the Stone or access the Vault. His simulacrum hosts an elaborate banquet at his large estate in the North Ward, intent on having the Cassalanters and the party attend. He also extends invitations to the Masked Lords and Laeral Silverhand, hoping to use the event to simultaneously oust the Cassalanters and the players. The players will undoubtedly be wary of meeting with him again, but the party also offers them a perfect opportunity to expose Manshoon to the city’s leadership. If the players have been helping the Cassalanters in any way, they can count on the nobles to back them up at least as far as not incriminating them and perhaps supplying alibies. Manshoon will have fabricated evidence that the players are members of the Cassalanter death cult, as well as eyewitnesses who can testify that the players set off the Trollskull explosion. He has also managed to get his hands on Renaer, who — supposing the players rescued him prior to Fireball! — has been blackmailed by Manshoon to claim that the players kidnapped him and planned to open the Vault with his blood.

How to thwart Manshoon

If the players have played their cards right, they have allies in at least one or two of the other factions. Sergeant Cromley can speak for them, and so can the Black Viper, Esvele, who only wants her father dead. Xanathar can supply them with a doppelganger as a spy at the party, who can knock Renaer unconscious and take his place, effectively eliminating that claim. If the Cassalanters are allied with the party, they will lie and say the party was with them at the time of the explosion in Trollskull Alley, which could be hard for witnesses to corroborate. However, the word of powerful nobles holds sway. Furthermore, at a signal from Lord Cassalanter, one of the Masked Lords — who is part of the cult — will sow doubt on Manshoon’s claims as to the presence of a death cult, insisting that the Cassalanters tithe generously and regularly to the church of Lathander in the Castle Ward. This benefits both the players and the Cassalanters, who will expect servitude from the players in return for their assistance.

If Manshoon is thwarted

He becomes irate and orders his goons to lock the mansion down. It becomes a mad scramble, and the players must navigate the fighting — which is considerable considering the number of powerful spellcasters at the party. If they can escape, they are considered free of guilt by the Waterdeep government, and they should expect the Cassalanters to collect on their debt if they helped establish the party’s innocence. The Cassalanters escape, as does their plant in the Lords. Laeral Silverhand and a few others apprehend Manshoon if the party doesn’t, which will be difficult considering his skill with magic (use the simulacrum statistics on p.208).

Further Complications

Just because Manshoon has been thwarted doesn’t mean his organization is thrown into utter shambles. The Doom Raiders, who admittedly play a relatively small role in this depiction of the adventure, take over — at least they appear to. In reality, the true Manshoon remains free of imprisonment and is in hiding within Waterdeep. From here, he commands the Doom Raiders. This changes the tone of the Zhentarim, who become less of a crime family and more of a cartel. This suits Manshoon fine, but some Zhents chafe at the development and leave the business. How this changes Waterdeep is up to you. The Zhentarim abandon their search for the Stone, but the Cassalanters and Xanathar likely do not, and seek the Vault’s contents with increased tenacity.

Closing Thoughts

This is a long-winded way of getting Waterdeep into playable shape, increasing the fun at the table, and embracing the tone of a dark, scummy city of sin. The villain's encounters play with ideas of how to confront your players without going straight to initiative, and show ways a villain might elect against or be prevented from full-fledged violent action.

Linked here is the full write-up, which is in Microsoft word. It's a lot more to go through than what's presented in this post, but hopefully it helps some of you envision a Dragon Heist that actually plays like the noir mystery, vigilante justice, intrigue mash-up it's meant to be.

Oh! I said I would go into why Jarlaxle isn't in the adventure. He's just product placement for WotC and his whole depiction in the adventure in chaotic lulz, so I chose to omit him.

Happy gaming!

Source: reddit.com

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