Rogues’ Gallery: The Xanathar

Rogues’ Gallery: The Xanathar

The Xanathar is one of the four main antagonists of Waterdeep: Dragon Heist, and it may well be the best-known of all of them. The Xanathar has appeared on the cover of three D&D books in the past 4 years: the Monster Manual, Xanathar’s Guide to Everything, and now Waterdeep: Dragon Heist. And while we all know the Xanathar to be a beholder, few people in the Forgotten Realms do. Most who know anything about the Xanathar at all simply know that “he” is a mysterious crime lord that has organized one of the mightiest criminal enterprises in Faerûn—other than the Zhentarim, that is.

Todd Kenreck interviewed Chris Perkins and Mike Mearls about the desires of our favorite beholder for the Stream of Many Eyes. His interview provides an excellent big-picture look at the Xanathar and its organization. For more information, including details about the Xanathar’s identity and its unusual history, read on.

The Xanathar at a Glance

The Xanathar that graces the cover of Waterdeep: Dragon Heist is not the first beholder to bear that title. That’s right, not name, but title. There have been many Xanathars over the centuries, each with their own motivations and neuroses. Beholders only live for a single century, and most die long before that at the hands of adventurers or others of their power-hungry kind. The last known Xanathar was named Zushaxx, a young and power-hungry beholder that came to Waterdeep to replace the previous Xanathar, who had grown bored of managing the massive criminal network of the Xanathar Guild.

This information comes from the article “The Xanathar: Beholder Crime Lord of Waterdeep” and an adventure titled “Eyes on the Ball,” both by Derek Myers and found in Dungeon Magazine issue 206. That adventure, however, took place in the year 1379 DR—more than 100 years before the present day in the Forgotten Realms of about 1490 DR! Even if the true name and origin of the current Xanathar is important—these details weren't covered in Xanathar’s Guide to Everythingthe title of Xanathar has been passed around so much over the years that you should feel empowered as a DM to create your own psychotic monster to run the Xanathar Guild, even if you are running things “by the book.”

The current Xanathar is, in Chris Perkins’ words, “paranoid to the extreme, and tyrannical in nature.” It clings to sanity by the barest of threads, and even its own minions fear its wrath. It craves power and flattery over all things, which puts this crime lord in a strange quandary. As with all paranoid narcissists, the Xanathar wishes to be beloved and feared by all, especially by those with power, but is so suspicious of others that it hides away from everyone out of fear that they might kill and usurp it.

The Xanathar Guild and Skullport

The Xanathar operates a massive thieves’ guild known as the Xanathar Guild, and its members operate all over the Sword Coast—in Waterdeep, Baldur’s Gate, Luskan, and even the Underdark beneath the Sword Coast. According to Myers, the Xanathar keeps several lieutenants that manage guild operations while constantly scheming and plotting against one another to curry the beholder’s favor. Odds are, all four lieutenants mentioned in Myers’ article are dead or have fled from the Xanathar’s service. The Xanathar Guild’s leadership, other than the Xanathar itself, is currently a mystery.

For centuries, the Xanathar Guild has operated out of Skullport, the Port of Shadows. This city of pirates and slavers was first identified as a mass of blocky structures in southern reaches level 3 of Undermountain in the Ruins of Undermountain boxed set. It was then explored in greater detail in Skullport for AD&D second edition. Skullport has long been a haven for the worst of humanity, as well as some of the most terrifying intelligent monsters, such as illithids and yuan-ti. Many drow and duergar from the lower levels of Undermountain and the Underdark also made Skullport their home.

The Spellplague devastated the Port of Shadows. As described in “Backdrop: Skullport” by Matt Goetz in Dungeon Magazine issue 200, a slaad named Azriim all but completely destroyed the port by collapsing its cavernous roof, and the blue flames of the Spellplague tore through the port only a few years later, scuppering efforts to rebuild Skullport. For many long years, the Port of Shadows was abandoned by all—presumably including the Xanathar and its thieves’ guild. Even in its destitute state, however, the Skulls—an order of thirteen flameskulls with dreams of domination—ruled the port as they had for centuries.

Even amidst the devastation of Skullport and the tyranny of the Skulls, it seemed that the Port of Shadows was not yet doomed. An adventurer named Miriam Sequora discovered mithral and ancient Netherese artifacts in the ruins, and her finds and persuasive charm drew fellow explorers and treasure seekers to join her. Given that Chris Perkins has revealed that the Xanathar is once more residing in Skullport, it seems that the Port of Shadows has been reborn, in some part thanks to Sequora’s efforts. Nevertheless, since this is the first time Skullport has appeared in a fifth edition product, the details of Skullport’s current government, economy, and inhabitants are unknown in this day and age.

The Xanathar and the Death Masks Crisis

In 2016, Ed Greenwood wrote a book titled Death Masks, in which the murder of four Masked Lords of Waterdeep shook the city to its core. I highly recommend that people planning on running Waterdeep: Dragon Heist read this book, as it gives important insight into the city of Waterdeep in the 1490s. The Xanathar is one of the suspects—no spoilers if it is or not, though! For some reason, during the Death Masks crisis, the Xanathar conspired with other evil forces to drive the Zhentarim from the city. The Xanathar’s motivation for this is unclear. Did it fear competition? Did it learn of the Manshoon clone that is now lurking within Waterdeep and fear the potential power of the Zhentarim? Does this have anything to do with the hidden gold central to this adventure?

Whatever the reason, the Xanathar is once again an active force in Waterdhavian politics. He’s back, and more dangerous than ever.

The Xanathar is but one of the four modular antagonists of Waterdeep: Dragon Heist. Who are you most excited to see enact their schemes within the City of Splendors?

Disclosure: James Haeck is a co-author of Waterdeep: Dragon Heist. 

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, and is also 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 two feline gazers, Mei and Marzipan. You can usually find him wasting time on Twitter at @jamesjhaeck.


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