Dragon Heist Diary: Part One

As much as we complain about it being tired and predictable, there’s something rather pleasing about kicking off a campaign with the immortal line: “You’re all sitting in a tavern…”

When it comes to Waterdeep: Dragon Heist, the tavern in question is The Yawning Portal – a classic adventurer’s inn poised over an enormous pit that drops down into an impossibly dangerous dungeon. It’s a loud, raucous place stuffed to the gills with a cast of both heroes and villains.

The first DMing challenge of the campaign, in fact, lay in trying to keep on top of this gallery of high-level foes and friends. However, I’m certainly glad that I gave it a solid try, as a handful of the faces on display that very first night would go on to have surprisingly serious impacts on the rest of the game.

The biggest focus of that first session wasn’t the heroes already lounging about The Yawning Portal, but the trio that had just walked in through the door.


The party our Thursday night group put together was a modest one, with only three members. Honestly, I was a little concerned this would end up making the by-the-book combat encounters too hard, but thankfully the team ended up assembling a party that was about as balanced as you could hope. In fact, it even slotted neatly into the classic Fighter/Rogue/Spellcaster triumvirate that’s been forming the basis of D&D parties for decades.

Our heroes were:

Flynn Lancaster (Halfling Rogue) – The swashbuckling son of a pair of famous adventurers. He was called to adventure when his parents failed to return from one of their journeys, deciding to begin his search in the place they were last seen – Waterdeep. While finding his parents is Flynn’s main goal, he’s also determined to see the world and prove himself a brave hero too.

Vigil (Tiefling Celestial Pact Warlock): Once a member of a cult worshipping the Archdevil Mephistopheles, Vigil was turned to the side of good by a bound angelic spirit and a band of adventurers. For more than 20 years he served as an agent of the Harpers, having been introduced to the spy network by Flynn’s parents, who happened to be among the adventurers that helped free him and became some of his closest friends.

Barric Strongarm (Halfling Fighter) – The tragic orphan is a common D&D trope, but while Barric was indeed an orphan his childhood was decidedly wholesome. Shortly after being abandoned in a lonely mountain settlement he was taken in by a loving dwarven family. Trained as a warrior (and as a dwarf) from an early age, Barric wanted nothing more than to be a hero and make his parents proud. While on the road to Waterdeep he encountered Flynn battling with monsters and ran to the halfling’s aid without a thought.

Small Fish, Big Pond

The first encounter in Dragon Heist is a curious one. For one thing it involves a Troll – a creature that could easily wipe out an entire platoon of first-level adventurers. For another, it really helps to drive home the fact that while they’re in Waterdeep the party are unlikely to be the scariest things around.

Ideally, they aren’t even meant to fight the troll, but rather the cloud of bat-like Sitrges that flap off its emaciated body as it emerges from the dark pit in the floor. The task of felling the big monster is instead supposed to fall to Durnan – the ex-adventurer who runs the tavern – who charges it armed with a Vorpal Greatsword and a full four attacks per turn.

In most campaigns I’d take a pretty dim view of kicking off with a battle alongside an incredibly overpowered NPC. The heroes are meant to be, well, the heroes, after all.

This time, however, most of the party didn’t seem to be let down by the fact that the innkeeper totally outclassed them during the battle. Instead, they viewed it as s glimpse of what was yet to come. “Take a look at how cool this sword is,” they heard. “One day you could have one just like it.”

Yes, they were small fish right now. But Waterdeep seemed like just the kind of place where they could grow and grow and grow.

On the subject of weaponry, the halfling fighter, Barric, was particularly taken with a thoroughly shiny magical battleaxe belonging to one of the many NPCs hanging about the periphery of the battle. The axe, he was told, was a sentient artefact named Azure Edge and its wielder was Meloon Wardragon, a prominent member of Waterdeep’s premier adventuring group Force Grey.

When Meloon raised a tankard and gave a nod to the impressionable halfling, Barric gave an audible cry of joy. Soon, he swore, he’d be a mighty warrior just like that.

Blood in the Streets

The rest of the session was a little more relaxed. The heroes were approached by Volothamp Geddarm, author of many books including Volo’s Guide to Monsters, and asked to track down a drinking buddy of his. Eager to get cracking on their first quest the party wandered into town.

Along the way they party had their very first run-in with Waterdeep’s City Watch, who were cleaning up the aftermath of a street fight between rival gangs. In the book the watchman warding them away from the crime scene is just a nameless guard, but when the players pulled the usual trick of asking for names, I tossed the question back to them. What was this dwarven guard called?

In the end, they settled on something appropriately dwarf-ey and the previously anonymous watchman became Sargent Stoutkeg – dour, predictable and thorough pillar of the community. And though none of us knew it at the time, they’d just conjured one of the most important NPCs of the campaign out of thin air.

This is one of the highlights of Dragon Heist, as well as one of the things that can make life tricky for DMs; the sheer quantity of NPCs.

The full cast list stretches into the dozens and may well even top out at over 100. Not all of them will be particularly important or even memorable, but players have a weird habit of latching onto unexpected background characters and dragging them into the spotlight.

Ultimately, however, this is probably a price well worth paying. The sprawling collection of bystanders, heroes and thugs helps to make Waterdeep come alive. It creates a network of relationships and ideas that the players truly come to rely on. Even when we were only a few sessions in, when the heroes ran into a road block their instant response was “oh, we know someone who can help with this.”

This, I think, is probably a sign that the world is doing what it should.

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