Waterdeep: Dragon Heist’s Darkest Choice

This article contains major spoilers for Waterdeep: Dragon Heist, especially the Cassalanter storyline.

Things can get dark in Waterdeep: Dragon Heist. But the darkest moment of all is not in the story with the beholder crime lord. It’s not even in the story with one of Faerûn’s greatest dark wizards. This grim honor belongs to the new villains on the block: Lord Victoro and Victoro Ammalia Cassalanter. The most horrific moment of the entire story happens when the player characters make a no-win choice at the end of the Cassalanter storyline.

If you want your players to consider the consequences of their actions and the weight of their duty as heroes, set Dragon Heist in summer with the Cassalanters as your villains. At the end of this story, the following choice lies with the heroes. Who dies: one hundred unsuspecting people, or two innocent children?

Let’s back up.

The Cassalanter’s Bargain

This is your last chance to turn back before the spoilers really kick in. Seriously, if you aren’t DMing Waterdeep: Dragon Heist, you should consider backing out now. Because we’re about to crack open this adventure and pick through its guts for the seeds of this bleak, decisive moment. It all started when Victoro and Ammalia were younger. Victoro Cassalanter was the heir to one of Waterdeep’s wealthiest noble families, and he and his beautiful and clever wife had one son, Osvaldo Cassalanter. Even by this time, however, the Cassalanters were devil worshipers. Yet even with all their privilege, Victoro and Ammalia longed for more.

Some time ago, “Ammalia and Victoro signed a contract with [Asmodeus], trading the souls of their children for power, good health, and long life. The soul of Osvaldo, their eldest son, was taken immediately, and he was transformed into a chain devil” (Source). Victoro and Ammalia are not good people. They did not make a deal with Asmodeus out of desperation. They were already wealthy beyond imagining, and they traded the soul of their eldest son for an embarrassment of temporal riches. But as with all Faustian bargains, the Cassalanters’ greed would come to haunt them.

The Cassalanters did not just pay for their power, health, and longevity with the soul of their eldest son. They promised the souls of all their children. And as the Dark One’s own luck would have it, Ammalia bore twins. Terenzio and Elzerina Cassalanter are now eight years old, and their parents have learned that Asmodeus plans to take their souls when they turn nine years old later this summer. Ammalia and Victoro are not heartless. They are selfish, cruel, and greedy, but they do love their children. They regret losing Osvaldo to Asmodeus’s bargain just as much as they love the power they have gained from it.  

In short, the Cassalanters owe Asmodeus the souls of their twin children, Terenzio and Elzerina, and he will come to collect before the end of the summer.

The Way Out

But the Cassalanters do have a way to renege upon their deal with Asmodeus. I wouldn’t put it past Asmodeus to have included this clause fully understanding that the Cassalanters would want to back out after seeing how Osvaldo suffered. (Osvaldo has been transformed into a Chain Devil, and the Cassalanters keep him hidden away in the rafters of their house.) Asmodeus profits greatly off of this secondary clause of the deal, for he will agree to spare the souls of the Cassalanters’ present and future children if they deliver to him “one shy of a million gold coins and the sacrifice of one shy of a hundred unfortunate souls.” Asmodeus would profit greatly from this; simply by the numbers, 99 souls is a much better deal than two, and he needn’t so much as lift a finger to obtain them!

And if you select the Cassalanters as your villains for Waterdeep: Dragon Heist, their plot to save their children’s souls requires them to find the Stone of Golorr, enter the Vault of Dragons, and abscond with the half-million gold pieces interred there. The players need to stop them… right? They’re the bad guys. They’re devil-worshipers planning on paying nearly one million gold coins and sacrificing nearly one hundred innocent people to Asmodeus as tribute in order to make up for their mistake! That seems like a more than worthy adversary for any group of adventurers.

“Aye, There’s the Rub”

Perhaps you’ve seen the trolley problem this poses to any would-be heroes who seek to defeat the Cassalanters. It’s actually a sort of reverse trolley problem; if the characters actively oppose the Cassalanters, their actions will save the lives of 99 innocent Waterdhavians from being sacrificed to the Hells, and they will also recover the cache of gold for the city. However, in doing so, they condemn the Cassalanters’ innocent children to damnation. The Cassalanters’ greed has not damned them. If they covered their tracks well, they will emerge from this entire sordid affair as—still—one of Waterdeep’s wealthiest, best respected, and powerful families. Their children, however, will suffer for eternity.

It’s a grim day for the player characters to see their actions—their victory!—lead to the loss of two innocent souls.

But the characters have to take action. After all, defeat is—by the numbers, anyway—much worse than victory. If they do nothing, or worse, lose to the Cassalanters, 99 souls will be sacrificed, and the half-million gold they fought so hard to protect will be handed over to Asmodeus on a silver platter.

Are your players willing to make this choice? Over the course of their adventure, they will have likely met Terenzio and Elzerina. They may have even befriended them. The “goal” of Waterdeep: Dragon Heist is to claim the half-million gold pieces for yourself and keep it out of the hands of the villains. But if victory means losing your two friends, would you still seek victory? Would you instead seek to ally yourselves with the villains just to save their innocent children? Even if it meant sacrificing 99 other souls you’ve never met?

If your game has already passed their crucial juncture, which path did your party choose? Which choice do you suspect your party will make? Or will they make another choice altogether?

“I Don’t Believe in the No-Win Scenario”

A truly determined party might seek a third option. The heroes have found themselves in a Kobiyashi Maru situation, but in the word of James Kirk, some parties “don’t believe in the no-win scenario.” How would you go about saving not only the 99 innocent souls and 999,999 gold pieces the Cassalanters plan on sacrificing and the souls of their two children? Osvaldo, I regret to opine, is probably a long-lost cause. Consider some options, and maybe you’ll be ready for your players when they try to pull a fast one on you.

Pulling one over on the Supreme Master of the Nine Hells himself is no small feat, especially for 5th-level characters. Will you wait ‘til 15th level or so and launch an attack on Nessus itself to reclaim Terenzio and Elzerina’s souls? Will you try to challenge Asmodeus to a fiddling contest? (In the right game, with the right DM, that might work!) What would you offer in exchange for the souls of these children?

Something to think about.


James Haeck is the lead writer for D&D Beyond, the co-author of  Waterdeep: Dragon Heist and the Critical Role Tal'Dorei Campaign Setting, the DM of  Worlds Apartand a freelance writer for Wizards of the Coast, the D&D Adventurers League, and Kobold Press. He lives in Seattle, Washington with his partner Hannah and his fiendish yowlers, Mei and Marzipan. You can usually find him wasting time on Twitter at @jamesjhaeck.


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