Waterdeep: Dragon Heist – The Villains

Herein, we discuss the four main villains of Waterdeep: Dragon Heist and try to make them more villainous.

Dragon Heist cover full
After 6 months of running this campaign, I finally get around to talking about the five guys on the cover. I’m very punctual.

One of the big selling points about Waterdeep: Dragon Heist is the modular, mix-and-match design that allows the DM to choose one of four main villains and which season the adventure takes place in. Frankly, the seasons and their seasonal effects are merely window dressing that you will probably incorporate once and then forget about, but choosing the villain, that’s a pretty big deal, right? Well, yes and no.

The four villains are all really cool for separate reasons and each one pays homage to the legacy of the Forgotten Realms. But when you realize that by picking just one villain then the entire adventure is suddenly shrunk by 75% and everything feels smaller as a result. On top of that, only one villain actually has a dastardly plan to stop. The rest commit a couple of white-collar crimes, like bribery and blackmail, hardly the stuff of legendary evil. So, let’s look at each one and see if we can’t make them a little more villainous. And then we’ll discuss how to use all four villains in one mega-campaign.

Jaraxle Baenre

Jaraxle square
Jaraxle Baenre. Dark, dashing, and debonair. Just ask him. 

Let’s start with Jaraxle Baenre. Jaraxle is the perennial frenemy of Drizzt Do’Urden from the best-selling R.A. Salvatore novel series. Jaraxle is a drow elf and leader of the shadowy Bregan D’aerthe faction. He is also the secret ruler of the city of Luskan. But while Drizzt is honest and honorable, Jaraxle uses stealth, deception, and lots of disguises to get what he wants. And what does Jaraxle want? He wants to find the gold so that he can return it to the people of Waterdeep so that they will be willing to accept the city of Luskan into the Lord’s Alliance. What? This goal actually feels rather noble. It is, and I love it.

It fits really well with Jaraxle’s ambiguous and shifting morality. But we still need a villain. I propose that not everyone in the Bregan D’aerthe shares Jaraxle’s altruistic goals. A splinter group within the organization wants to perpetuate the war against the surface elves. I made the true villain here be Soluun Xibrindas, who is one of Jaraxle’s Gunslinger lieutenants.

Drow Docks
One of these guys has been a very naughty drow.

Soluun and those loyal to him have a plan to destroy the Temple to Seldarine (a major elven temple) during an elven holiday. They plan to blow up the temple using their stockpile of smokepowder, killing many innocents. The players intercept an unmarked blueprint and have to discover the target and stop the plan. Jaraxle is unaware of this plot and is actually appreciative if the players foil it. Although he won’t be thrilled if Soluun is killed.

Victorio & Ammalia Cassalanter

Next up are the Cassalanters. Lord Victoro and Lady Ammalia are the heads of one of the most powerful noble families in Waterdeep. Their Forgotten Realms heritage goes way back to 1st edition as evil, devil-worshipping nobles, with one notable exception. Caladorn Cassalanter rejected his evil family to become an honorable Masked Lord and eventually served as a respected Open Lord. Sadly, he’s been dead for a century, and the family is once more fully evil.

In fact, The Cassalanters are the only villains with an actual plot and they have the darkest ending of all of them. If they succeed, hundreds of people will die a gruesome death, and even if they fail, two innocent children will suffer eternal damnation and torture. Apparently, we are playing Call of Cthulhu now.

Cassalantar Children
Once the players get involved, these kids are screwed.

I actually like their dastardly scheme, but if you are uncomfortable with this grim moral dilemma, then you could remove the children’s souls from the equation and have the Cassalanters performing their sacrifice to merely acquire more power. Also, I would allow that even if the Cassalanters do not receive the gold, then their plan will still proceed. They had the gold; they just didn’t want to spend their own money. This will force the players to actively stop the villain instead of just passively (and unknowingly) causing the plan to fail. You can also add a condition that allows the villains to lose and yet still save the children. Perhaps by having the players switch the poisoned wine so that the cultists drink it instead. Still pretty dark, but the children get to live as penniless, disgraced orphans, so yea.


Next up is Manshoon, the evil leader of the Zhentarim faction. Except there is one problem. Manshoon is actually the leader of a splinter Zhentarim faction that is separate from the established Zhentarim faction run by the Doom Raiders. Oh, and there’s one more problem. The real Manshoon is dead and this is one of his clones. The Manshoon Clone Wars (no relation to Star Wars) was one of the major storylines of 3rd edition D&D, that ended with just three clones surviving; one of them choosing Waterdeep as his base from which to plot his conquest.

Manshoon square
This Manshoon lost his left arm and replaced it with a metal one. My players call him Thanos.

And what is his horrific plan? He will use the gold to bribe and coerce the Masked Lords to make Manshoon the Open Lord. Mwah-ha-ha. Ooh, he is so despicable. And lame. This is easily the 2nd worse plot of all. Imagine playing West Wing the Roleplaying Game, with all the excitement of senate judiciary committees, gaining bi-partisan support, managing lobbyists, deciphering polling numbers, and unleashing the almighty filibuster! This is Manshoon’s master plan? Boring!

Let’s make his plan a little more visceral. Manshoon has kidnapped and replaced several Masked Lords with replicas. He has altered his clone ability to make perfect clones of other people, who are fully loyal to only Manshoon. Mirt the Moneylender, as contact for the Harpers, calls on the players to investigate several Lords who are acting suspiciously. (Yes, this is very similar to the Meloon/intellect devourer side quest, but on a grander scale.) During an encounter with one of the cloned Lords, the clone attacks the players. He is subsequently killed, but now the players are wanted for murder of a Lord, making them go on the run. Later, there will be open warfare on the streets between the legit Zhentarim, Manshoon’s Zhentarim, plus the Xanathar Guild, and the City Watch. Ultimately, the players will have to fight through all these factions to get to Kolat Tower to rescue the kidnapped Lords and prove their innocence.

The Xanathar

Syglar Theft
Wait a minute! Syglar doesn’t need a bath. He lives in water! Come back here!

And finally, there is The Xanathar, the most famous villain of the four and the only one with his own D&D book title. The Xanathar is the Forgotten Realms’ worse kept secret villain; everybody seems knows that he is a beholder. The Xanathar has been a paragon of evil in Waterdeep for over a century, with all manner of sinister schemes and dastardly deeds to his credit. So, what is The Xanathar’s evil plot this time? He doesn’t have one. Nope, nothing. Seriously, he just wants the gold for… reasons?  Sure, there are a few random acts of chaos being committed by a few random minions, but there is no real imminent threat.

So, I stole the bad guy’s plan from the Waterdeep novel City of Splendors where a group of mutated creatures called the Amalgamation (great name) are trying to collapse a bunch of buildings by weakening their foundations. Here, The Xanathar uses several Umber Hulks who have been burrowing under multiple targets. This time, all of The Xanathar’s targets are chosen for extremely silly and petty reasons.

He wants to destroy the office of the Waterdeep Wazoo because they wrote an article saying that the Xanathar Guild is not as powerful as it once was. He wants to destroy the Yawning Portal because it serves Goldfish Soup. He wants to destroy the Blackstaff Tower because he hates the color black. He wants to collapse The Godcatcher because he wants a giant statue of man worshipping him in his living room. (Xanathar thinks that the orb the statue is holding is actually his likeness.) And so on.

Do I look like I care if a hundred surface dwellers die? I want that statue!

While the players are in Xanathar’s Lair for any of the reasons given in the book, they find a list of “Things to Destroy” that looks like it was written by a child. (The Xanathar has no hands and writes with his mouth.) The players have to discover the nature of the threat (of course, no one else believes the threat is real) and then they have to defeat the umber hulks to foil this plan.

The best part about these new evil plans is that they have to be actively stopped by the player’s actions and not “just caused to fail”. The players actually have to deal with the villains, or at least their level-appropriate henchmen, and have motivations beyond just keeping the gold away from them. Now let’s see if we can incorporate all four villains into one massive campaign.

Waterdeep: A Year of Villany

Waterdeep 4Seasons Villains full
Here you can better see how each villain is placed in his proper season. Photoshop rules!

If you are playing Dragon Heist with just one villain, then it doesn’t really matter what season you play through. You can use the appropriate season as written in the book, or change it to suit your campaign. Each villain does have an event which is held during a particular holiday, but that to can be changed along with the season without affecting the story. Just use my copy of the Faerun Calendar to pick the appropriate festival day for the season you want. For example, I changed the Jaraxle season to Spring, so I altered the Sea Maiden’s Faire to hold their parade on two days; Dragondown, which occurs on Kythorn (June) 20th to open the carnival season, and the Midsummer Festival at the end of Flamerule (July) to close the season.

More important than choosing the season however, is choosing the order in which the players will face each villain. You could have all four villainous plots occurring at the same time, but this will confuse and overwhelm your player. However, it is best if you can sow the seeds of the next villain’s scheme as each season progresses. While the heroes are dealing with one villain, they hear rumors or find minor evidence of the next villain and his plan.

Waterdeep Wazoo 1
Reading my paper every day will make you erudite and informed about things that never happened in a world that doesn’t exist.

The easiest way to do this, it by using the newspaper. When I write a new issue of the Waterdeep Wazoo, the major article usually describes a recent event the players actively participated in. This lets the players feel cool that they made the paper, even if it is a fictitious one, and allows me to remind them of important or even missed plot points without me having to tell them specifically. But at least one of the secondary articles is used to set the stage for the next villain. For example, while my players are dealing with the Cassalanters, they read an article about a suspected Masked Lord who goes missing, but then turns up unharmed. This refers to Manshoon, who will be the next villain, and hints at his nefarious cloning scheme.

Feel free to create your own, but I created my villain order based upon the threat level of the villain and the scope of their plan. To that end, my order is: Jaraxle Baenre, The Cassalanters, Manshoon, and finally The Xanathar. Jaraxle actually likes the heroes and doesn’t want to kill them. Plus, in my story, it is really his underling who is the true villain, and Jaraxle may even become an ally. The Cassalanters would rather figuratively destroy the players than literally kill them, but their plan is more diabolical than Jaraxle’s. My Manshoon’s new plan is even more insidious, and despite what the book says, he would definitely just kill the players if they oppose him. Last, it is only fitting that The Xanathar be the final villain. He is undoubtably the best villain Waterdeep ever had. He is The Joker to Waterdeep’s Batman. He is completely unpredictable, lethal, whimsical, and terrifying. He has the best dungeon of all the villains. Multiple stories revolve around him, and he has numerous plots to unravel.

Nestaurs 4Seasons
The book gives you these four evocative portraits of the seasons but then never sends the players to this part of town.

Once you have your villain order, you just need to pick a season to start in. Also, you don’t need to have one villain per season. You could have two of them occurs at roughly the same time, or even have all four take place over the course of 4 – 6 months. Whatever works. In my campaign, the players arrived in Waterdeep at the beginning of summer, so that is when we started. I played it so that each villain occupied the main stage for one full season.

As I said, Jaraxle was first and it made more sense to have The Sea Maiden’s Faire in town during the summer anyway. The Cassalanters were my villains for the Autumn, and I had their story culminate on Lair’s Night (Marpenoth 30th (October)). Given the demonic, gothic, and scary nature of their story, it seemed appropriate to have it end on the Waterdeep equivalent for Halloween. I kept Manshoon in Winter, as I liked the bleak nature of his story to coincide with the gloomy nature of the season. Finally, Xanathar in the Spring is the perfect scenario. I love the juxtaposition of the season of hope and rebirth to be completely obliterated by the chaos and lunacy of a deranged beholder.

Stone of Golorr
My players thinks this thing is a loaf of bread.

The last thing we need to manage, is what to do with the Stone of Golorr. This McGuffin is likely to annoy your players the most if you keep denying them the ability to use it. There are a couple of ways to delay them from using the stone and finding the secret vault, but you have to be very careful how you implement it and you should only do each tactic once, or you will perturb your players.

You can have someone steal the stone. After the players first obtain the stone, ask them who has it and how he stores it. They will probably insist that they keep it on their person inside their bottomless pockets (which didn’t even exist in medieval times). But even then, they gotta sleep. I would have the Black Viper steal the stone and deliver it to the first destination of the next villain’s chain of events in Dragon Season, as if the Black Viper was the Nimblewright.

Black Viper square
Hey, maybe this rich and detailed character can actually do something in the adventure now.

If that particular chain of events is time-sensitive, meaning that all the events occur quickly without a break in-between them, then I would have the players wake up just as the Viper makes her getaway and the players chase her to the next destination. But if there is a break in the chain’s sequence, such as Fenerus hiding the stone and getting arrested as happens during the Jaraxle chain, then you could have the players work to uncover the identity of the Black Viper. Maybe she left a clue at the scene of the crime, or they could use the detective, Vincent Trench, to track her down. The players would then need to convince the Black Viper to reveal what she did with the stone and the hunt for the stone can begin again.

Once the players recover the stone, you could use the fact that the Stone of Golorr requires attunement to use. And since the Stone is actually an evil, intelligent being, this might take a while. In my campaign, during this time, my players are called away from Waterdeep on an urgent mission for the Lord’s Alliance. They have to travel to a remote island and deal with a Yuan-ti invasion that will run my group through The Hidden Shrine of Tamoachan adventure in Tales From The Yawning Portal. This has the added benefit of taking the players’ mind off the stone for a while.

Lost Shrine thumb
I can’t wait to run this insane adventure.

When the players return to Waterdeep, you could have the Stone of Golorr reject attuning to the player’s character. If your player is willing, I would privately roleplay a solo encounter, where the stone takes control of the player’s actions. The player wakes up in a strange part of town and has no idea how he got there. More importantly, he no longer has the stone. The group then has to retrace his steps as each stop gets more and more ludicrous (like the “A Night to Remember” mission in Skyrim). Finally, they discover where the player brought the stone and the next villain’s encounter chain can begin properly.

Finally, the players have the stone again and one of the players is actually attuned to it. But before the stone will reveal the location of the vault, the players have to prove they are worthy by collecting the three required keys first. While they are running around town doing this, they have to fend off more and more attacks from the remaining villain. This should bring them into conflict with the villain’s plan as well.

Yawning Portal NPCs
Anyone of these fine NPCs is ready and willing to sacrifice themself to the gods of forced plot contrivances.

Alternatively, if you want to have the group play through another encounter chain (beware that they may be sick of these by now), you could possibly steal it once more. This time, the thief is someone important to the party, perhaps one of the friendly faces chosen at the start of the adventure or another NPC that has become part of the player’s inner circle and has access to Trollskull Tavern. This NPC has been consumed by an intellect devourer, essentially killing this NPC. For me, this would also play into the fact that The Xanathar and his mind flayer, Nilihoor, are my final villains. After setting in motion the villain’s encounter chain, this devoured NPC would attempt to kill the players, confirming the betrayal, but allowing the party to reconnect with the encounter chain.

In the end, once the party has discovered the location of the vault, the final encounter could include a battle with any or all of the villains and their henchmen that are still alive. You could also have one of the villains (Jaraxle) show up and fight by their side. If they managed to becpome allies beforehand. That would be a cool turn of events.

Dragon Horde Kids clean
If the players were smart, they’d just let the dragon kill the greedy villains and then pick up the pieces.

One last note about the Villain Encounter Chains. You will have to severely modify, shorten, and in some cases, remove entire sections of each chain. Despite the differences in flavor, all four Chains are very similar. Track down one person, chase someone to a new location, investigate that location to find out who the stone was passed to, chase that new person and catch him/her/it before the stone can be delivered to the villain. Plus, you can’t expect your players to believe that all four villains each have a mausoleum, a theater, an old tower, and a converted windmill as integral locations in their villainous scheme. How many windmills does Waterdeep have?

If you do use all four villains in this manner, I would limit the number of encounters in each chain to no more than five or six. Combine any superfluous ones. Eliminate some repetitive chase sequences. Change a theater into a market place; or make one of the old towers be The Hawk Man statue which has been hollowed out to make living space; etc. My Waterdeep Faction Missions PDF also has an Encounter Chain chart to help you modify and move the various locations within in each Chain. Here in the link. Waterdeep Faction Missions

Waterdeep Faction Missions

Finally, and obviously, pick just one location to be the secret location of the Vault of Dragons. Personally, I would use the converted windmill from the Jaraxle chain. This is the coolest location for a secret vault. Plus, the interior with all the bizarre paintings that come to life creating all manner of fantastical beasts for the players to contend with is one of the most imaginative pieces of D&D writing I’ve ever seen.

I would change all the other windmill locations in the various Chains to less memorable buildings (anything other than a windmill, let that one be unique). I would also mention this particular windmill as often as you can without being too obvious about. The secret vault windmill is in Sea Ward, which the players do not visit very often in the story, so it should not raise too many eyebrows when you mention it in passing.

Sea Ward Windmill square
The scariest dragons and the fiercest giants ususally turn out to be no more than windmills.

An example could occur while investigating the nimblewright following the Trollskull Alley explosion. “As you are walking toward the Temple of Gond, in amongst all the noble villas and upscale buildings you pass, I see a large windmill down one of the alleys. It is simultaneously odd to see here and yet somehow perfectly at home in this fantastical city, where one never knows what you will find around the next corner.” And then later, “As you are heading toward the Cassalanter villa and your destiny with the devil, you once more pass by the lonely windmill, its forlorn blades slowly turning, silhouetted by the full moon.” Once the windmill is revealed as the vault location, hopefully your players will have that “aha” moment when they realize that this location has been right in front of them the whole time.

This wraps up my thoughts about the excellent villains and their not-so-excellent schemes. Waterdeep: Dragon Heist is a great adventure, but like any adventure, it should never be played straight out of the book. It needs to be molded to fit your DM-style of play and, more importantly, altered to serve your players’ desires in your campaign.

Waterdeep Dragon Heist cover painting
Happy Hunting!

For more help in running Waterdeep: Dragon Heist, check out my Waterdeep: Dragon Heist Campaign Resources Guide. There are tons of tips and tricks; from running a fantasy metropolis, to managing factions & NPCs, to a full campaign diary that delves into every part of the adventure. Plus, I include every map, handout, and image I used to run the adventure.

As always, a story is only as good as its villain is bad, and Game On!

The counting of the villains shall be four. Neither count thee two or three, excepting that thou then proceed to four. Five is right out! – On the Allocation of Villainy, part 5. Three, sir. Three.

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