8 min read

The Guilds of Waterdeep

Finzu begins navigating the interconnected guilds of Waterdeep. Renaer makes good on his promise to translate the abyssal they found in the dark house.
The Guilds of Waterdeep

You can find my prep notes for free on Patreon.


The City Is Alive

The party left the cave as the sun began to rise. They watched as the light spread across the city, pulling back the night to reveal the City of Splendors.

The walking statues towered over the wards as Castle Waterdeep caught the first rays. They watched as the Luskan ships rocked in the bay as the Dock ward began to come to life. Blackstaff tower cast long shadows as the market below bustled awake. The green and the spacious City of the Dead stood in stark contrast to the compact Trades Ward. In that moment, standing above the city, there was true peace.

For a long time, they stood there watching, taking in the sights. It was only when Taman turned to ask if they should be going did he realize Hlam was now standing with them.

“Beautiful, isn’t it?” Hlam stated more than asked. The monk spoke a little philosophy and then turned to Finzu. He had recognized Finzu as a member of the Order of the Even-handed and approached him with a task. He offered to take him as a student. But first, he must seek out Dream Flake and Fate’s Hair herbs, steep them together and inhale the vapors. Then he was to come back and tell Hlam about his experience.

Finzu agreed and the party went back to the Yawning Portal for a long rest.


DM Note:

Sadly, Viigo failed a performance check… miserably

Upon waking, they walked to the Cassalanters to receive their loan. Crossing The Market, they ran into a large group of festival celebrators. The pack of people was dancing through the streets and playing instruments. As they passed the party, they attempted to pull Akta and Viigo with them. Akta straight up refused but Viigo did his best shimmy. Upon seeing the dance the lady smiled politely and let go of his hand before disappearing into the crowd.

Before continuing on, they grabbed the latest copy of the Waterdeep Sentry. Their exploits had made the front page, though with no mention of themselves.

Arriving at the Villa, a servant received them in the library before fetching the Lord and Lady. Exploring the richly decorated room they noticed a few oddities. The first was that the books on the shelves were for display purposes. There was no method of organization and the variety spanned the gambit. The second was a family portrait that hung over the mantel. They had met all but one member of the family, an older son. They also noticed a series of shelves that housed bottles of swirling mists. Investigating the bottles turned up nothing other than carefully written labels.

Once Ammalia arrived and after small talk and then asked if they could add 500 dragons to their loan. Ammalia stepped out for a quick moment to get Victoro’s sign-off. When she returned, her twins ran into the room after her. They introduced themselves, smiled, and asked many questions in rapid-fire succession.

Eventually, Ammalia sent them away. It was then that Taman stepped forward and asked about the older son in the painting. This seemed to pain Ammalia and she made a comment about “living with decisions”. Sensing it was a sensitive topic, Taman dropped it.

As they were leaving, Victoro emerged from his office. He explained that to kick off the festival season Waterdeep held a Grand Tournament. It would begin on Ches 19th and take place every three days for four rounds. Each group of fighters had to have a sponsor. He wondered if they would allow himself and his wife to do so. The party agreed, excited about the opportunity.

Guild Work

Their next stop was at Fellowship Hall. They met Broxley Fairkettle in a massive beer hall where he laid out the terms of their agreement. They paid the fees necessary to join the Innkeepers Guild. Since the official papers would take a while, Broxley then handed them a receipt. They could provide it to other guilds to prove their membership.

Broxley Fairkettle

Broxley Fairkettle

On their way to the Carpenter’s guild, they witnessed a man almost get run over by a horse and carriage. The books he was carrying were scattered across the street. Viigo knelt down to help the half-elf pick them up and noticed that they all had very advanced magic titles. The apprentice wizard introduced himself as Linden Tallowick and admitted that the books were not for himself; they were far too advanced. They were for Vajra Safahr, the Blackstaff herself. He told them she was always looking for good people and that he would mention them to her that evening.

Arriving at the impressive Carpenter’s Guild, they found themselves waiting in line. This took longer than expected but they eventually made it to the front. An elf, who was all business, informed them that they were quite lucky. A crew had become available that morning and they would be able to begin construction the following day. Finzu then asked about the possibility of breaking the payment up into installments. After some back and forth, they came to an agreement. They would pay everything but 500 gold dragons upfront. The remaining balance was due once upon completion of the job.

With the day beginning its transition into night, they stopped by a Weaponry in the Trade Ward. Akta turned over her longsword to be mended and Viigo purchased some iron ingots. They then went straight to the Yawning Portal.

Bar Talk

Once there, they ran into Renear speaking with Durnan at the bar. He was quite happy to see them. He had completed the translation of the Abyssal glyphs they had found in the warehouse. He found it rather distressing.

Translated Ruins

Translated Ruins

He told them what he could about the Cassalanters, being that he considered them more acquaintances acquired through his father than anything else. Yet, he knew that Ammalia often spent time with the poor in the Field Ward. He commented that they were well known for throwing the best Feast of Leirun. Unfortunately, he only knew that their eldest son had abruptly disappeared but no details.

They then asked Renear about Nimblewrights. Renear commented, “What an oddly specific question.” As it turned out, Mirt had been asking Durnan about Nimblewrights recently. For such a rare topic, it was coming up quite often.


This session was all about the Cassalanters and their ability to use emotions to manipulate the party. They had signed away their children’s lives to Asmodeus in exchange for power and money. Octavio, their eldest, had been taken immediately. What remained of him is now a chain devil locked in the attic at their villa.

Ammalia’s bleeding heart is a front. If they can’t come up with the 999,999 gold dragons required to pay their debt to Asmodeus, they need to sacrifice 99 souls. (This is an or instead of an and in my campaign.) Her work in the Field Ward accomplishes two things.

  1. Find 99 souls which they could sacrifice during the Founder’s Day feast. This holiday is when nobles open their doors up to the poor and feed them. It is also the last day before their payment is due. While their last resort, sacrificing that many souls takes a lot of planning and coordination.
  2. Her work with the poor projects a particular image. This is a misdirection against any suspicions that may arise due to rumors. This pertains to both their plan of sacrifice and their affiliation with the Cult of Asmodeus

Aside from the Cassalanters, Mirt has been busy. He has been asking about Nimblewrights because his spies have reported many surfacing in prominent places around Waterdeep. He is suspicious of the sudden influx of these constructs into the city and is looking for a way to discretely procure one so that he can disassemble it.

He has also been investigating the illicit drug trade in Waterdeep. Black Lilly, a drug akin to cocaine, has begun to show up everywhere. Through his spies, Mirt has been able to determine that the Xanatharians are responsible. He is now attempting to discern more about their operations.

Xanathar, on the other hand, believes that he has collected enough information that establishes Mirt’s involvement. Because of this, he is deciding what to do about the situation.


As you can probably tell from my prep notes, I didn’t have a lot prepared coming into this session. This was due to a combination of a busy out-of-game life and the fact that I didn’t have a great idea of what the party would do. Because of that, almost the entire session was improv. I relied heavily on my mini DM binder to create the encounters.

I did know a few things going in.

I knew that I didn’t want to waste the opening scene when the party sees Waterdeep at sunrise. I thought that it was a great opportunity to provide some history to the party in a natural way. It also gave them some perspective.

Almost every moment of the campaign is spent at ground level. They are constantly surrounded by buildings and citizens, focused on an objective. For anyone who has been to or lives in a big city, this might feel familiar. Despite all this life and motion, you can lose your perspective on things. Sometimes, standing at the heart of a large city can be the loneliest place on earth, no matter the number of people around you.

In hindsight, it served as a great metaphor for the greater narrative. While at the ground level they are running tasks and missions. Up here though, looking over the city, they can ‘see’ the scope of the campaign.

I spent most of the preparation for this session on the handouts.

The newspaper was important to me. Each article serves a purpose. They either tie to an action of the party, showing how the NPCs react, or lay the groundwork for future events and storylines. Can you spot them?

The party was never meant to notice all these. They are there so that they could notice them. The Alexandrian has a great rule-of-thumb he calls the ‘Three Clue Rule’. It states that, if there is something you want the party to pick up on, you need to present it to them in three different ways. While I wouldn’t consider these articles an official clue, I count them as bonus hints.

The second handout, and the one which took the most of my time, is what I call the Trollskull Matrix. I knew that my players would love running Trollskull Manor. I also knew that at least one of them would love a hyper-detailed way to manage and operate the business.

Because of that, I pulled together work done on the Obsidian Portal and structured it so that it was more consumable. This provides a plethora of decisions for them to make while building out the Manor. I thought of it as the science track in the Civilization games in which you unlock benefits after meeting certain criteria.

I’ll share the matrix in this post, but it deserves its own post given the level of detail.


Waterdeep Sentry


Trollskull Upgrades and Matrix

Below is a visual guide to the upgrade process that I gave to the party.