dragon heist

‘D&D Waterdeep Dragon Heist’: Session 1

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Image: Wizards of the Coast

Dragon Heist Session One: A troll walks into a bar…

The adventurers sat at a sturdy wooden table in the crowded Yawning Portal tavern, soaking up the atmosphere. And the mead. They had been in Waterdeep for just over a month and had some work as investigators, but tonight they were having a night off. They watched as a group of would-be adventurers prepared to make the descent into the fabled dungeon below the tavern. It would be a long time before they were ready to go down to Undermountain themselves. Suddenly the noise of gambling, drinking, and cheering was eclipsed by a shout from by the bar, “Ya Pig! Like killin’ me mates does ya!” A seven-foot-tall half-orc was struck by a wild, swinging punch from a man whose shaved head was covered in eye-shaped tattoos. “FIGHT!”

Last night was the first session in our new online Dungeons & Dragons Waterdeep Dragon Heist campaign and it started with a tavern brawl.

This article is the second in a series of session reports from the Dungeon Master’s perspective and it will contain spoilers. If you are a player in a Dragon Heist campaign you may not want to read on. If you are searching for a review of the campaign book then click here.

The Setup

After the conclusion of our Curse of Strahd campaign, I have taken on the mantle of Dungeon Master for our D&D group and we were all keen to get started with the new Dragon Heist campaign. We are playing via Skype and using D&D Beyond and Trello to keep track of characters and general campaign notes. So we are once more relying heavily on technology, and entirely at the mercy of the internet.

Naturally there were a couple of technical issues during last night’s first Dragon Heist session. For once it was my internet connection that was struggling to keep up, causing my screen to lag and my connection to drop. Note to self: I must remember to complete the ritual sacrifice more promptly in the future. Although I am running out of fresh kittens.

The party

Last week we held a Session Zero for character creation and came up with the party of heroes that would be braving the streets of Waterdeep. They are a small band of unproven investigators, mostly new to the city, but with big ideas of helping the innocent and fighting injustice wherever they can. And drinking.

They are:
Alan Crabpopper, Human Ranger – a private investigator and low level thug.
Dugg, Earth Genasi Fighter – estranged son from a noble family, House Rasznor.
Little Joe, Drow Sorcerer – a charlatan, channeling the spirit of John Wayne.
Arvene Galanodel, Half-Elf Cleric – avaricious trickery-domain priestess of Tymora, ex-city guard, ex-nun.

dragon heist
Image by Mat Philips

Startled by the erupting fight, the four adventurers looked around the room for cues. They hadn’t been in Waterdeep long and weren’t sure if they should intervene or not. The locals all seemed to be enjoying the spectacle and had formed a ring around the combatants. Beyond the crowd they could just about make out the half-orc who had been attacked. Dugg recognized her as Yagra, a mercenary he’d befriended days earlier. There were four other thugs standing alongside the bald tattooed man. Five against one seemed unfair. Dugg decided to join the fray.


It didn’t take long for those two magic words and our Dragon Heist campaign was underway. At first the players didn’t really know if they should interfere, but seeing as Dugg’s friend Yagra was under attack, they soon made up their minds.

Yagra and the lead thug clearly knew each other and were exchanging heated words as well as fists. The half-orc was at least a foot taller than the bald tattooed thug, whom she called AJ, but as soon as she swung her first punch, which connected with a loud crack, his companions all stood up from their bar stools, like a boy band after a key change, and entered the fray.

The first round of initiative saw Little Joe cast Minor Illusion on Yagra to make her seem fierce and demonic. Two of the thugs backed away as veins and muscles on Yagra’s arms stuck out and her eyes glowed red. “Look out!” called Little Joe, “This legendary warrior kills with one punch!”

Alan then foolishly tried to break up the fight and ended up getting smacked about by both Yagra and AJ. Dugg raced into the melee too and stood beside the half-orc ready to defend her, only to receive a critical hit from one of the thugs, taking 6 points of damage. Seeing him hurt, Arvene ran to Dugg, tapped his shoulder and cast Guidance, giving him a +4 advantage on his next attack roll.

Backstreet’s Back

Round two of combat saw the thugs gain the upper hand. In keeping with our old DM’s tradition of likening NPCs to famous musicians, I decided that tonight they would be played by the Backstreet Boys, so AJ was joined by Nick, Howie, Kevin, and Brian. And they danced and sang as they fought.

During this round, Little Joe had managed to miss critically with a Firebolt, burning a hole in the floor of the balcony that overlooked the main room; Alan stole a drink from a bystander and smashed it against a thug’s head; Dugg attacked the same thug (Nick) and managed to knock him out; and Arvene cast Sacred Flame at another but he managed to dodge the attack.

The thugs each landed their attacks, except Nick who was unconscious on the floor, and soon the players began to realize how weak and squishy their level one characters really were.

Luckily for them there were some friendly faces in the tavern. At the start of Dragon Heist, each player gets to choose one NPC from the Yawning Portal that they know, and during round three these friendly faces came to the fore. I knew these NPCs would come in handy and they’re a really useful way of tying the narrative together. They also each have a secret that the players might find out at later stages of the campaign.

Dragon Heist

Dugg’s friendly face is Yagra and she was the reason he joined the fight. She was clearly more powerful than he was, however, and stepped in front to protect him from the next couple of attacks.

dragon heist

Arvene’s companion was Bonnie the barmaid. As Arvene made her way through the crowd, Bonnie helped distract one of the thugs, allowing her to attack with advantage. She then smiled at her friend and went back to clearing up the mess of the tavern as the fight went on.

dragon heist

Little Joe was friends with Three-Strings, one of the bards playing lute in the tavern. Rather than help out Little Joe, he simply played the theme song for the Magnificent Seven, which gave him a point of bardic inspiration on his next attack. Thus inspired, Joe hit Howie with a Firebolt and dealt maximum damage, incinerating the thug, leaving only a smoldering trilby on the ground.

dragon heist

Alan’s friend was Durnan, the burly ex-adventurer and proprietor of the Yawning Portal. During this stage of the fight he merely leant on the bar, wet rag in hand, wiping the surface. At one point, when one of Alan’s attacks went wide and he left an arrow lodged in the ceiling, called out, “Oi! I don’t mind you fighting in here, just watch out for the upholstery!” He would soon become significantly more involved in the melee.


By the end of the third round, most of the thugs had been dealt with, only AJ was left standing. As Yagra lifted her mace to strike the final blow, a yell went out from Durnan behind the bar. “Troll!”

dragon heist

Everyone looked to see a large troll that had managed to climb out of the well in the center of the Yawning Portal and was attacking patrons in the bar. Most of the customers and staff either fled or ducked under tables at the sight of it, but Durnan and Yagra both raced to face the giant green monster. Six Stirges (weird blood-sucking, bat-like creatures that look similar to oversized furry mosquitoes) also flew into the tavern and began dive-bombing those that stayed behind. “We’ll focus on the Troll,” yelled Durnan. “Kill the Stirges!”

dragon heist

Following Durnan’s instructions, Alan, Arvene, and Little Joe focused their efforts on the Striges, ducking and diving as they tried to swat them out of the sky. A Firebolt from Little Joe took care of one and a couple of well-timed arrows from Alan killed another. With the help of Bonnie, Arvene managed to squash another Stirge, but not before it had latched onto her neck and began draining her blood.

Dugg, however, ignored Durnan and ran to help defeat the troll. Among the three of them, Durnan, Yagra, and Dugg, they managed to kill the troll, but it took just over three rounds of fierce combat in which Dugg was reduced to zero hit points and knocked unconscious.

As the troll fell to the floor and the last of the Stirges was taken care of, Dugg rolled his first death saving throw. He had five chances to roll three 10s or higher. Failure to do so meant death. And rolling a new character. Luckily, before that happened, Durnan called for assistance and Dugg was revived.

Volothamp “Volo” Geddarm

After two encounters in quick succession, the group needed a couple of moments to rest and recuperate. But they were approached with a proposition for work that they likely couldn’t refuse.

Alan and Arvene headed straight for the bar were Durnan had offered free drinks to all who had assisted in defeating the troll. As they began to discuss what just happened, a tall, thin man with a large floppy hat, a curly mustache, and puffy purple shirt approached them. “You be adventurers, am I right? I could use your help. My name is Volo Geddarm. Let’s find a table to talk.” END


I really enjoyed getting back in the DM’s seat for our premier Dragon Heist session and I ran it pretty much as written in the campaign book. An escalating brawl in a tavern is an excellent way to let the players get a feel for their characters as, let’s face it, combat is what they’ve all come here to do. Although as the campaign progresses, there will be a shift of focus away from direct combat. It was also a great way to show the players how squishy their 1st level characters are and how careful they’ll have to be in order to stay alive.

Having the friendly faces in play right from the start worked really well too, giving the players a reason to join the fight. I think that as our Dragon Heist campaign progresses, these NPCs will play pivotal roles in the story.

At the end of the session I didn’t award experience points, as we’ll be using the milestone method for leveling up, but they did each receive 10GP from Volo for agreeing to take on the mission. Dugg also found 3GP in AJ’s pouch, along with a petrified mouse and a temporary tattoo of an eye. Before the session I rolled a couple of times on the Trinkets table in the Player’s Handbook (p. 159) just in case anyone found anything, which came in handy. Incidentally, they could have also found the blueprints for a complex mechanical contraption scrawled on the back of a playing card, or a glass orb filled with water in which swam a clockwork fish – but I guess I’ll just save those trinkets for a later Dragon Heist session.

What did we learn?

DM Tip: Always have a list of names and attributes for your NPCs ready whenever you play. You never know when you’ll need to introduce the Backstreet Boys or a past adventuring party into the fray. I find it really useful to also have distinct features for each individual enemy, especially if combat involves multiple foes of the same type—e.g., five thugs. On paper they all look the same, but as soon as you start describing one as having a perfectly preened goatee, one wearing a preppy scarf, and one with a trilby, they instantly become more memorable and easier to keep track of in a fight. However it’s important to remember the names you give NPCs too—especially if they are already named in the story. In this Dragon Heist, the NPC I called AJ is actually called Krentz, so I will have to remember that if he becomes a recurring character.

Next week in our Dragon Heist adventure, our heroes will hear the full tale of Volo’s missing friend Floon Blagmaar and will take their first steps into the shady underworld of Waterdeep, City of Splendors. I wonder which pop stars they’ll run into next?

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