Xanathar: Everything You Need To Know About Waterdeep’s Mad Beholder Crime Boss

Beneath the winding cobbled streets, beneath the hallowed chambers of the Lords of Waterdeep, far below the City of Splendors’ towering spires and mighty walls lurks a dark secret. 

Known only to a few, feared by all — especially those who serve it — the sprawling dungeons beneath Skullport hide one of the city’s most influential figures, lord of Waterdeep’s underworld, the Eye Tyrant, the mad beholder himself: Xanathar. 

Welcome to our guide to one of the Forgotten Realms’ most iconic villains, who holds the seedy underbelly of Waterdeep in a vicelike grip — which is impressive for someone without any hands. 

Whether you’re setting out to run a Dungeons & Dragons 5e adventure that features the Xanathar — like Waterdeep: Dragon Heist or its nominal sequel, Dungeon of the Mad Mage — or want a compelling villain for just about any crime caper, this guide is your crash course in everyone’s favorite psychotic floating eyeball. 

In this article, we’ll give you an introduction to the Xanathar’s history and personality and how to run this unique villain at the table. 

But first, in case you haven’t guessed, the Xanathar is a beholder. 

Uh, yeah. If you’re planning on running Waterdeep: Dragon Heist, maybe don’t forward your players this article. It’s a reasonably big spoiler for the module. 

I got to play in this adventure recently, culminating in a desperate heist of the mad beholder’s lair, and, oh boy did the other players who didn’t know Xanathar was a beholder lose their minds when they found out. Very cool. 

So, top tip for DMs who want to run an adventure with Xanathar: DON’T LET PEOPLE KNOW HE’S A FREAKING BEHOLDER! It’ll be better that way, I promise.

So, for the uninitiated…

What Is a Beholder? 

Beholders are one of  D&D’s most enduringly iconic monsters.

Indeed, they’re probably the most recognizable foe in the whole hobby that wasn’t drawn from hundreds (if not thousands) of years of myth and legend, like vampires, werewolves, demons, devils, and the eponymous dragon

These aberrations have been a part of the game since the very earliest editions and have remained largely unchanged throughout the ages. 

It’s important to note that many aspects of a beholder will differ from one to another. These aberrations are beings of raw, unstable magic.

While some beholders are covered in thick, leathery skin, others may sport glittering chitin or glistening iridescent scales, fur, stone, or any other substance you could care to imagine.

This also can’t be used as a way of tracing a beholder’s family line as beholders don’t reproduce or form any of the familial attachments that are the hallmarks of other creatures. 

They reproduce by having violent nightmares about themselves that sometimes manifest in the waking world as new beholders — or beholder-adjacent things like gazers.

They hate these creations. They hate other beholders. They hate anything that isn’t a beholder. 

While each beholder is unique in their own awful way, they all share several important characteristics.

Beholders take the form of a large sphere (about 8 feet in diameter) with a single vast eye at its center. Wherever the eye’s gaze falls, the light grows pale and gray as all magic in that area fades. 

Each beholder is also festooned with 10 stalks, and on the end of each is another eye.

From these eyes, the beholder emits random bursts of magical energy that can do everything from charm and beguile a creature to vaporize it instantaneously.

The level of control a beholder has over its eye rays is a matter of some debate.  

We go into beholders in more detail here, but here’s what you need to know. In addition to being giant floating laser orbs that hate everyone, every beholder exists in a state of rampant paranoia, jealousy, and fear.

“Beholders are convinced that other creatures resent them for their brilliance and magical power, even as they dismiss those lesser creatures as crude and disgusting. Beholders always suspect others of plotting against them, even when no other creatures are around.” – Monster Manual

Who Is the Xanathar? 

The Xanathar is the beholder that rules the Xanathar Guild — Waterdeep’s unofficial thieves’ guild.

Probably the most important thing we can do to kick things off here is to nail down why this beholder is sometimes called Xanathar and sometimes called the Xanathar.

The answer is that there was once a beholder called Xanathar, and the beholder that currently runs the Xanathar Thieves’ Guild is not that Xanathar

That’s right, much like everyone’s favorite black-clad buccaneer with a razor-sharp wit (and a razor thin mustache), “the Xanathar” is a title that passes from one beholder to another throughout the centuries. 

You see, it’s the name that’s so important for inspiring the necessary fear. No one would ever surrender to the dread pirate Wesley.

Of course, unlike the Dread Pirate Roberts, Xanathars do not willingly surrender their title and position to upstarts, and they certainly don’t make plans to retire and live like kings in Patagonia.

This is a title that changes hands violently and in utmost secrecy. 

It probably helps that very few people other than the upper echelons of the Xanathar Thieves’ Guild actually know that their boss is a beholder, and the various Xanathars put a great deal of effort into brutally murdering anyone and everyone who starts asking too many of the wrong questions. 

The only real clue to the fact that The Xanathar is actually just Another Xanathar is the hidden room within the beholder’s lair where the pickled, putrefying remains of the Xanathar’s predecessors float in large tanks of brackish fluid.

Few people have ever seen this room. Fewer still have lived to tell anyone else it exists.  

History of the Xanathar(s)

“Few of the thieves working for [Xanathar] knew they labored and risked their lives for an eye tyrant.” — Villains’ Lorebook (1998), pg. 122, AD&D 2e, TSR 

Based on the evidence found in Waterdeep: Dragon Heist, the current Xanathar is probably the 14 beholder to bear the title, given the four embalmed beholder corpses on display in the secret vault and the nine copper urns containing the remains of disintegrated beholders arrayed in alcoves around the walls. 

It’s possible that these dead beholders are simply unsuccessful challengers to the Xanathar’s throne.

However, the fact the current Xanathar keeps the zombified corpse of another beholder who failed to take its place as a glorified guard dog elsewhere in the dungeon suggests that it wouldn’t go to the effort of preserving the remains of just any beholder; only a Xanathar is worthy of being immortalized in secret deep in the bowels of its lair. 

The first beholder to establish a foothold in Waterdeep was indeed called Xanathar.

The entity arrived shortly after the Lords of Waterdeep crushed the city’s “official” thieves’ guild, driving the city’s criminal element deep underground and rendering it leaderless. 

“The Xanathar came to the City of Splendors as cargo in a caravan coming from Zhentil keep.” 

Originally a servant of the Zhentarim — a faction of evil wizards who seek dominion over the entire Sword Coast — the Xanathar arrived in Waterdeep and sensing a power vacuum in the wake of the local thieves’ guild’s destruction, immediately betrayed its former masters, establishing itself as the secret power at the heart of criminal activity in the city. 

Before long, however, another beholder arrived on the scene. This one — also in Waterdeep on the orders of an evil organization and just as loyal to its former masters — was known simply as “the Eye.”

It killed the first Xanathar but recognized the fact that it would be easier to preserve the now-dead beholder’s network of connections without making the previous crime boss’ death public. And thus a murderous dynasty was formed. 

Today, the Xanathar rules its domain from the shadows. The beholder’s natural state of raging paranoia, mixed with a healthy dose of common sense, means that Xanathar believes that its organization will only survive if it remains hidden from the Lords of Waterdeep. 

As such, the Guild employs primarily freelance criminals, primarily to create plausible deniability if the authorities ever come knocking.

To further this impression (not to mention fulfill the overwhelming desire found in all beholders to collect rare and strange trophies), Xanathar uses its extensive spy network to collect secrets, information, and rare fragments of knowledge from throughout the Forgotten Realms. 

Within the guild itself, the number of subordinates who know that their boss is a Beholder has fluctuated over the years.

Early on, just four key lieutenants (a rotating cast of violent psychopaths, blackmailers, torturers, and assassins) could even find their way through the twisting, trap-filled passageways that separated the beholder’s lair from the rest of the guild’s headquarters. 

These days, a larger number of lackeys know the beholder’s true nature, though many of them would likely have rather remained in the dark.

Cruel, capricious, and paranoid, the Xanathar is a difficult boss to work for, and it frequently turns its eyestalks (or fearsome jaws) upon the members of its own organization who displease it. 

Mostly, however — in perhaps the most extreme example of “managing your manager” found in the Forgotten Realms — Xanathar’s lackeys keep the beholder on a mostly even keel.

Of course, this could all go to the nine hells in nine handbaskets immediately if something happened to Xanathar’s best and only friend. 

Sylgar

The only thing the current Xanathar loves, respects, or feels any positive emotions toward in any way is its best friend, Sylgar. 

Sylgar, for those of you not in the know, is a goldfish.

A perfectly ordinary, very mortal goldfish that dies rather frequently as goldfish are wont to do.

Whenever this happens, the passing of Sylgar briefly throws the guild into a state of utter panic and frantic activity while they try to replace the previous fish before the beholder finds out.

There’s even a halfling who sleeps in a small alcove next to Sylgar’s tank with the sole job of keeping an eye on whether or not the fish has gone belly up.

If Sylgar died and Xanathar found out, well… Everyone agrees it would be best if they never found out what would happen next. The smart money is on indiscriminate and widespread application of the beholder’s disintegration ray.

(Pointing out the irony of a beholder who is secretly the latest in a long line of beholders sharing the same identity getting upset about the death of the latest goldfish in a long, long line of Sylgars probably wouldn’t help all that much.) 

Running The Xanathar 

If you want some advice on running Xanathar in combat, check out our Creature Feature on beholders or this excellent article from The Monster’s Know What They’re Doing.

If you want to make Xanathar feel mechanically unique — as well as some great advice on how to make these aberrations feel truly aberrant — watch this fantastic video by Dael Knigsmill. 

In this section, I want to talk about roleplaying Xanathar. 

I think the Xanathar is a really interesting prospect to run as a dungeon master. The beholder is, in many ways, all the character traits and foibles that define the archetypal mob boss turned up to 11.

It’s Al Capone, Scarface, and Tony Soprano all rolled into one giant ball (literally) of malevolence, ambition, and coke-addict-level distrust. 

The paranoia, the sudden outbursts of violence. Hell, even the secret identity has notes of Season 2 of The Sopranos about it. 

Now, okay fine, it takes about five seconds to pick up on the fact that it’s fantasy Jabba the Hutt.

However, as easy as it is to play Xanathar as a corpulent, gluttonous lech who is both crime boss and rancor rolled into one, I think we can take a slightly more subtle approach by looking at the more grounded, non-fantastical crime bosses who inspired Jabba (and Xanathar) in the first place.  

Humanizing Xanathar

That brings me to my first big note about playing the Xanathar, which is that all mob stories (all the great ones at least) make us like the mobsters. Well, we may not like them, but at the very least, we are compelled by them. 

Whether that means understanding what makes them tick or glimpsing a little of what brought them to where they are today — giving your players some insight into Xanathar, making him more than just a CR 13 speed bump, is hugely important.  

Reconciling the well-drawn three-dimensional crook with a heart of gold with the murderous, incurably cruel and paranoid aberration that can vaporize you with a glare might initially seem tricky, but it’s the line that all great mob stories walk.

Tony Soprano’s moments of brutal, abject violence and psychopathy are only powerful because we’ve spent the past 15 episodes watching him put out mundane fires, fix inane family problems, and mope about the house eating gabagool. 

For example, Waterdeep: Dragon Heist suggests that if the beholder is in the vault beneath Xanathar’s lair filled with the remains of previous Xanathars when the PCs come in, it’s floating about solemnly, staring at its former selves floating in embalming fluid.

If there’s one thing that powerful mobsters love to do, it’s contemplate their legacy and mortality (preferably while wearing a dressing gown).  

I think there’s a lot of material that suggests you play the Xanathar as unstable, unpredictable, and ill tempered, ready with a death ray at a moment’s notice.

While these characteristics should always be bubbling near the surface (why else are its crew so utterly terrified of it), adding layers of civility, charisma — charm, even — on top is going to do a hell of a lot to make meeting the crime boss of Waterdeep into a truly memorable experience. 

I also think that the profound sadness, the ennui of a lot of figures in mob stories is something you can lean on heavily.

A Xanathar that’s aware that all its underlings fear and despise it, that’s aware that its goldfish dies every couple of months and is replaced, but who thinks that this level of fear — this adherence to the legacy of every Xanathar that came before it — is the only way the empire will survive is a much more interesting character than some mad, cackling lunatic with a death ray. 

My other — more concrete —  note is inspired by a line on Xanathar found in the AD&D sourcebook Waterdeep and the North.

Waterdeep and the North Cover
© Wizards of the Coast

(The book itself confines its description of Xanathar to barely half a page, but the cover actually features the beholder doing its best Marlon Brando impression.)

The section on Xanathar notes that “Xanathar is a creature of pleasures — it enjoys finely prepared foods… scented oils, and spiced southern tobaccos and herbs.” 

The line is reinforced by a section in Waterdeep: Dragon Heist that notes various ways the PCs can enrage Xanathar to the detriment of its organization.

In addition to obvious stuff like killing Sylgar and breaking the machine that lets Xanathar sleep without horrible, gazer-spawning nightmares, one of the simplest ways to destabilize the beholder crime boss is to kill its personal chefs.  

In addition to giving Xanathar a giant, noxious cigar so phallic it would make James Gandolfini jealous, I think that it can be very effective to portray the Xanathar as having not only expensive but refined and elegant tastes. 

Imagine this but, you know, with more eyes. You can even keep the shirt.

Beholders are undeniably gruesome.

Letting the players see the inherent contrast in the grotesque, levitating, alien monstrosity chowing down on highly refined sweetmeats (as the late great Jack Vance would have put it, exquisite viands) or talk with encyclopedic knowledge about different vintages of wine, can do a lot to amplify how scary the Xanathar is while simultaneously reminding the adventurers that it’s not just another bag of hit points to be murdered and looted.  

Final Thoughts 

Whether you want to play Xanathar as just another dungeon boss — it certainly works really well in that regard — or a tortured, sympathic, yet irredeemably violent crime boss suffering from its own success, it’s honestly going to be hard to run this iconic villain in a way that your players won’t remember. 

While I’d maintain it’s really important that they don’t start out knowing that Xanathar is a beholder — or that it’s just another Xanathar — I think finding ways to let them find this out over the course of the adventure is absolutely paramount.

If any old beholder can become the Xanathar, why can’t a party of adventurers with the right attitude and a bit of creativity?