Kirukeskai

Kirukeskai, also called the Eye, was an elder orb who was the first beholder to hold The Xanathar as a title instead of a name.

Description
Kirukeskai was an elder orb whose body advanced to the limit of a beholder and was therefore very big for its race. It was an elder orb of very advanced age and was wrinkled specimen of its species.

Personality
Beholders in general were paranoid creatures. Kirukeskai's case was noteworthy even by that standard. Beholders generally did not step out of their homes and generally worked through intermediaries, but Kirukeskai exclusively worked through intermediaries and never went out of its fortified homes in Skullport and the southern half of the third level of Undermountain, which it managed because these homes were linked via portal. In fact, only the Masters of the Xanathar's Guild knew that it was a beholder or that it was not the first one to rule their criminal organization. Another group that knew of the former fact were the eleven eyes of Xanathar, though it was not clear whether they knew of the latter fact.

Beholders in general were megalomaniac creature and Kirukeskai was no exception. It viewed all creatures on the surface as slaves for its taking and it viewed humanoids who tried to become closer to beholders by becoming ocular adepts as arrogant pawns.

Beholders in general believed themselves to be intelligent. The Eye was very intelligent even by beholder standards and a competent businessman.

Kirukeskai was a cruel parent who charmed its offspring into subservience until thez matured and turned them later into death tyrants.

Elder orbs were beholders who were immortal and could not die due to natural causes. Their aging stopped after a long period of age-induced physical deterioration. It was not clear whether the Eye did not know about the properties of an elder orb or whether it was not aware that it was one but fact was it feared death from old age. It drank potions of longevity and ordered the kidnapping of mighty clerics to cast heal or regenerate on it. The former was a completely needless operation due to its immortality but the latter allowed it to temporarily offset parts of its aging effects.

Physical Abilities
Kirukeskai was an old elder orb. This meant that it was not as agile as other beholders and while it was big, it was not much physically stronger than other beholders because its advanced age deteriorated its physical capacities.

Magical Abilities
Kirukeskai was old and as mentioned above, his body underwent deterioration. Two of his eyestalks, the ones, which allowed him the casting of disintegrate and flesh to stone, completely stopped working and needed magical care as administered by aforementioned kidnapped priests to work. A third eyestalk, the one allowing the Eye to cast charm person, worked only half of the time.

Every elder orb had sorcerous powers. The Eye's sorcery was strong even by that race's standards. It could additionally cast death fog, demand, dimension door, ESP, fly, spell turning, wall of fog, and wall of force once per day.

Tactics
As a general rule, the Eye did not kill its enemies outright. Instead it tried to keep enemies alive for interrogation purposes.

Possessions
The Eye wore a ring of proof against detection and location on one of its eyestalks and used beads of force, a cloak of arachnida, oil of timelessness, a ring of feather falling, a staff of curing, and a wand of lightning. It also carried with it a bag of holding of the maximum size. Its most unique item was one that worked on one end like a vorpal longsword and on the other end a gauntlet that worked with the missile storing property, which it could use like a hand.

Kirukeskai was constantly surrounded by entire swarms lurking stranglers and eyeballs.

Activities
Kirukeskai was a crime lord who ran the Xanathar's Thieves' Guild, also called the Xanathar's Guild.

As expected from a thieves' guild, its focus lay on thievery but the organization was special in that it had a second focus in the form of slavery. The Eye as a ruthless businessman, who expanded his organization's slavery size to one that rivaled Zstulkk Ssarmn's slavery business and the Shadow Thieves' thievery business. Kirukeskai also expanded into the smuggling business and managed to take over the shares of Misker, who shared the top smuggler position with Malakuth Tabuirr.

He controlled all beholders of the Undermountain and those who did not want to follow its lead were under serious danger and were forced to leave for the surface or other places away from Waterdeep.

Xanathar's Thieves' Guild
Kirukeskai was the head of the Xanathar's Thieves' Guild. Organizations run by beholders generally had flat hierarchies and the Eye was no exception. He had direct control over the eight Masters who were each responsible for one aspect of the guild and under whom were only two hierarchy steps.

The Master of Slavery viewed Kirukeskai, or to be more precise his continued supervision, annoying. It was rumored that he wanted to become independent.
 * Ahmaergo

Out of the Masters the Mistress of Slavery worked with the Eye the longest and had therefore a better understanding of him.
 * Avaereene

The Master of Assassins was opting for a position of power in Waterdeep after his master died.
 * Colstan Rhuul

The Master of Smuggling and Thieving liked working under Kirukeskai because it left him more freedom in how he pursued his job.
 * Ott Steeltoes

The Master of Magical Defense and Information Gathering wanted to become a member of the Lords of Waterdeep, something the Eye encouraged. He got on his master's nerves for taking vacations to meet mermaids and there was contingency spell on the Master to teleport his dead body back for raising.
 * Randulaith

The Master of Blackmail, Extortion, and Information Gathering was working for the Eye only grudgingly to the point that she plotted against her leader (Kirukeskai was aware of her plans).
 * Shindia Darkeyes

The Master of Enforcement and Mercenaries was happy working for the Eye because unlike its predecessor, Kirukeskai was willing to feed his vanity with praises.
 * Slan Thurbel

The Master of Information Gathering was the Eye's accountant and manager of its spy network. He knew so much that Kirukeskai was prepared to use a large amount of resources to get him back or killed in the case of his capture.
 * Slink Monteskor

The eyes of Xanathar were the truly trusted spy-assassins of the Eye. They and not the Masters were the real force behind the guild's success. They also received a magic item called an Eye of Xanathar.
 * Eleven Eyes of Xanathar

Lords of Waterdeep
The Lords of Waterdeep were a hypothetical enemy of the Eye. They were enemies of any thieves' guild but they had no clue that the Xanathar's Thieves' Guild was even active.

Beholders
Kirukeskai was the master of the beholders of the Undermountain. The original Xanathar was killed by Kirukeskai and its position was usurped by it. The Eye kept the name and changed it into "The Xanathar" to make it sound like a title.
 * Xanathar

A beholder from the same hive as Kirukeskai, these two were rivals on the smuggling market. The Eye took over its business share. Misker hid away from the Eye's violence.
 * Misker

Drow
The Eye came from the Graypeaks Hive. That beholder hive was destroyed by the drow of Ched Nasad. It was willing to set aside its enmity with Misker to attack particularly worthwhile caravans from that city.
 * Ched Nasad

Kirukeskai and these Vhaeraunite drow had a complex relationship. On one hand, they were competitors on the slavery market, on the other hand, they were allies in the form of the Iron Ring, the followers of Vhaeraun were a part of. Truth was that Kirukeskai found this competition amusing.
 * Dark Dagger

History
The Eye, as Kirukeskai was nicknamed, was an ancient, wrinkled, and paranoid beholder of the Graypeaks Hive.

The Eye arrived in Skullport in 1205 DR, already a slaver in search of a greater market. In time, his business and his organization grew. At one point, he re-organized his organization into a semi-autonomous model and retreated into the background, spreading rumors about his demise or retirement. Soon, most people forgot about the beholder slaver and in 1304 DR the Agents of the Eye were simply a large slaving ring in Skullport with no association with beholders.

Meanwhile, the Eye investigated the Xanathar Thieves' Guild, a powerful thieves guild, and in time discovered that they were also led by a beholder, a beholder of a different hive. Thus the Eye decided to take control, by killing and taking the position of Xanathar. The Eye discovered all Xanathar's secrets and at the same time manipulated another Skullport beholder, Uthh, into wanting to kill Xanathar.

Eventually, Uthh fought Xanathar in his lair; Xanathar slew Uthh but was too weak to resist the surprise attack of the Eye. The Eye killed Xanathar and inherited all his holdings.

The Eye pretended to be his predecessor but, in order to avoid problems, said that "the Xanathar" was just a title. Afterward, the Eye gathered together the Agents of the Eye and the Xanathar's Guild.

The Eye then controlled an extensive slaving operation in Skullport, rivaled only by the Iron Ring and the resurgent Shadow Thieves. It also muscled in on Skullport's smuggling operations, at the expense of its beholder rival, Misker the Pirate Tyrant.

The Eye extended its control over all the beholders of Undermountain, forcing those who refused to bow to its rule to flee into the Underdark or to the surface. It sole remaining rival, Misker, was forced to flee into the depths and hid in the abandoned Trobriand's Graveyard.

In 1379 DR one of his minions, Shynlar Draal, was captured by the Unyielding Sword mercenaries hired by the slaver Lanador alongside some other elves; the Xanathar supported an adventuring party hired by the City Watch to investigate the matter and defeated the slaver.

It was rumored that the Eye was in fact the second beholder to assume the name of Xanathar. In truth the Eye was killed by an adventuring band under orders of the Lords of Waterdeep and secretly aided by an other beholder that assumed the identity of the Xanathar.

Rumors & Legends
Kirukeskai was at least the second beholder to carry the name "Xanathar", meaning there was a slight chance that he was not the second but later incarnation of "the Xanathar", though he was definitely the first to use it as a title instead of a name.