Xanathar (original)

Xanathar was one of most infamous beholders of the Realms and the crime lord of the Xanathar Thieves' Guild in Skullport.

History
Xanathar originally came from the Anaurian Hive.

Xanathar was originally a follower of Xantriph of Zhentil Keep. He was sent by the Zhentarim to Waterdeep to destroy the Lords of Waterdeep and establish a ruler allied to the Zhents. However, he soon started to act independently, establishing a new thieves' guild and disappearing. He later led a great thieves' guild and only his four lieutenants—Slan Thurbel, Slink Monteskor, Ott Steeltoes, and Shindia Darkeyes—knew his true nature and aspirations.

Beginning around 1354 DR, another beholder set its sights on the Xanathar's Thieves' Guild. Already the leader of a slaving ring also based in Skullport, the beholder known as the Eye desired to increase its power and influence by taking over the thieving organization. Over ten years, the Eye studied the Xanathar's Thieves' Guild and questioned charmed people in the know, and found subtle similarities in how their two groups behaved, things only a beholder would recognize. It thus learned the Xanathar was a fellow eye tyrant from a different hive, and plotted to eliminate a rival and seize more power in one swoop. Xanathar remained completely unaware as, over a few years, the Eye's investigations revealed the location of its lair.

Xanathar once accidentally petrified Ilserv, the illithid emissary of Ch'Chitl.

In the mid-1360s DR, Xanathar attempted to organize the disparate thieves of Waterdeep into a new guild. However, the effort was thwarted and Xanathar was defeated by bold adventuring companies commanded by Lord Piergeiron of the Lords of Waterdeep, and was the latest such effort by 1367 DR.

Xanathar's ruin came at last in the late 1360s DR, when the Eye, via its agents, carefully manipulated another Skullport beholder, Uthh, and tricked it into attacking Xanathar in the sewers under Waterdeep. Although Xanathar defeated Uthh, it was left weakened and, taking advantage, the Eye arrived and easily killed Xanathar. Afterward, the Eye replaced it, telling Xanathar's former minions that "the Xanathar" was but a title. Persuaded by charm spells and by death rays at dissenters, most agreed to stay and serve it. "The Xanathar" took full control of the Xanathar's Thieves' Guild and gained great power and influence by 1368 DR.

Personality
Xanathar greatly enjoyed being a crime lord just under the noses of Waterdeep's Lords. He was confident in his power and his inconspicuousness to the Lords.

Xanathar loved luxury and pleasures, and very much enjoyed well-prepared foods (provided by Steeltoe), scented oils, and spiced tobaccos and herbs from the south. His appetite was huge, and included to people. When not engaged in crime, he relaxed in a great glass tank of scented water.

Xanathar was devious.

Activities
Though the Xanathar's Thieves Guild, Xanathar controlled most of the crime in Waterdeep. Rather than operate as a true "thieves' guild", and thus risk the attention of the Lords of Waterdeep, he instead worked entirely through freelance thieves via third parties, so that no-one could reveal his whereabouts, identity, or even existence. Xanathar was the major supporter and advocate of the hundreds of small criminal enterprises in Waterdeep. He was amused by the Lords' claims that no thieves' guild existed in Waterdeep.

Xanathar collected much information about the surface world, also via third parties, and used this to make his plans. It was rumored he knew the most about Waterdeep's sewers and their connections to major buildings and to Undermountain. His libraries closely tracked the powers and vulnerabilities of Waterdhavian mages. However, all information in these libraries was written by Slink in a cipher.

However, Xanathar's best defense was secrecy, and he would go to great efforts to maintain it. Operatives who wondered who was in charge was targeted for death by Slan's ritual killers. He also engaged in misdirection, with defenses against magical detection on his lair and having his organization function not at all like a real thieves' guild. He was sure the Lords would tear apart the city's sewers to locate his lair, if they but of his existence.

Relations
Xanathar was served by his "Four Councilors". They met with him regularly and in turn dealt with others in the organizations. No one else knew of Xanathar's existence, let alone that he was a beholder.

Shindia Darkeyes, the half-drow thief, was Xanathar's lieutenant and personal favorite. She oversaw blackmail and exortion. She helped Xanathar kill Uthh, but could do nothing to save it from the Eye. Afterward, she served the Eye grudgingly while plotting its downfall.

Slan Thurbel was Xanathar's mercenary leader and hitman, but Xanathar insulted continuously him and, in Slan's words, did not "respect his talents". Glad Xanathar was dead, Slan much preferred the Eye in charge.

Slink Monteskor was Xanathar's bookkeeper and information gatherer, with web of spies and snitches in the poorer parts of Waterdeep.

Ott Steeltoes was a dwarven pirate who provided Xanathar's delicacies.

Xanathar also owned two charmed intellect devourers and a winglet of six gargoyles for the defense of his lair.

Anyone who managed to find and invade Xanathar's lair was interrogate for information, briefly kept as a pet, and finally eaten by the beholder.

Residence
Xanathar laired in a hidden chamber behind a secret door in the sewers below Waterdeep, accessed by a series of trapped passages. None but he and his Councilors knew of its existence and the safe route in, and the few who stumbled into it soon met their ends there. The lair was opulently furnished, and held several treasure vaults and libraries.