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Hasan Sabbah, the Grandmaster of Shadows

“Master of Shadows: Unravel the Enigmatic Life of Hasan Sabbah, Leader of the Assassins!”

Hasan Sabbah
  • Alias: The Old Man of the Mountain
  • Gender: Male
  • Race: Human
  • Occupation: Leader of the Assassins
  • Religion: Nizari Ismaili sect
  • Allies: Devoted followers of the Assassins
  • Enemies: Powerful political and religious figures, especially the Seljuks and Crusaders
  • Abode/Base of Operations: Alamut Fortress in Persia
  • Nationality: Persian
  • Languages: Persian and Arabic
  • Alignment: Neutral Evil
  • Affiliation(s): Nizari Ismaili, Assassin Order
  • Significant Others: Notable followers and disciples within the Assassins’ ranks

Hasan Sabbah, a enigmatic and resolute figure, leads a clandestine order of assassins on a path shrouded in shadows and secrets. Born into a world of turmoil, he harbors an unyielding determination to shape the destiny of his followers and achieve an elusive vision.

From his early years, Hasan was drawn to the idea of clandestine power, and he believed that certain individuals, acting as instruments of fate, could alter the course of history. Fueled by a profound desire for control and driven by a thirst for knowledge, Hasan established his mountain stronghold, Alamut. There, he gathered like-minded individuals and nurtured their unwavering loyalty, guiding them toward a greater purpose.

Hasan’s deep-seated fear revolves around chaos and the unpredictable nature of human existence. He sees the world as a place of uncertainty and disorder, and this uncertainty is something he cannot abide. To counter this fear, he has founded the Order of Assassins, where discipline, obedience, and meticulous planning reign supreme.

In his pursuit of order, Hasan Sabbah envisions a world where his assassins hold the balance of power, a world where calculated actions can shape destiny. His ambition is not driven by a lust for personal gain but rather by an unwavering belief that a select few can mold history for the greater good, even if it means walking a treacherous path of darkness. Through his Order, he seeks to establish a structured world order where he and his followers will be the hidden hand that guides civilization’s course.

Hasan Sabbah

Medium humanoid (human), Neutral Evil

Armor Class 15 (studded leather armor) Hit Points 90 (20d8) Speed 30 ft.

10 (+0)16 (+3)14 (+2)18 (+4)16 (+3)12 (+1)

Skills Insight +7, Deception +4, Persuasion +4 Senses Passive Perception 13 Languages Persian and Arabic

Challenge 10 (5,900 XP)

Background: Sect Leader. Hasan has advantage on Charisma (Persuasion) checks when dealing with members of his sect.

Master Manipulator. Hasan is a master of persuasion and manipulation. He has advantage on Wisdom (Insight) checks to discern others’ motives.

Spellcasting. Hasan Sabbah is a 12th-level spellcaster. His spellcasting ability is Intelligence (spell save DC 16, +8 to hit with spell attacks). He has the following wizard spells prepared:

  • Cantrips (at will): Mage Hand, Minor Illusion, Prestidigitation, Message
  • 1st-level (4 slots): Charm Person, Command, Comprehend Languages, Detect Magic
  • 2nd-level (3 slots): Invisibility, Suggestion, Detect Thoughts
  • 3rd-level (3 slots): Dispel Magic, Major Image, Tongues
  • 4th-level (3 slots): Charm Monster, Confusion
  • 5th-level (2 slots): Dominate Person, Modify Memory
  • 6th-level (1 slot): Programmed Illusion


Multiattack. Hasan makes two attacks with his dagger.

Dagger. Melee Weapon Attack: +6 to hit, reach 5 ft., one target. Hit: 5 (1d4+3) piercing damage.

Sect Influence. Hasan can use his influence to command members of his sect to carry out covert operations, espionage, and assassinations. He has a network of skilled spies and assassins under his control.

Leadership Cult. Hasan Sabbah’s followers are fanatically loyal to him and will go to great lengths to carry out his orders. He can rally his followers to perform daring and dangerous missions.

Psychological Warfare. Hasan is known for his use of psychological warfare. He can use his spells and influence to sow discord and confusion among his enemies.

Lair Actions

  • Cryptic Ritual. Hasan Sabbah can perform cryptic rituals in his hidden lair, gaining insights and knowledge to further his cause. These rituals have various effects and may grant him visions of the future.
  • Symbolic Assassinations. Hasan can order symbolic assassinations to strike fear into the hearts of his enemies. These assassinations are carried out in such a way as to send a message to those who would oppose him.
  • Hidden Agendas. Hasan Sabbah’s lair is filled with clues, coded messages, and hidden agendas that only the most astute can decipher. Exploring his lair is a dangerous endeavor.


Counter Manipulation. Hasan can use his charm and persuasion to attempt to counter any efforts to manipulate or deceive him.

Legendary Actions

Hasan Sabbah can take 3 legendary actions, choosing from the options below. Only one legendary action option can be used at a time and only at the end of another creature’s turn. Hasan regains spent legendary actions at the start of his turn.

  • Dagger Attack. Hasan makes one dagger attack.
  • Psychological Warfare. Hasan uses one of his spells (2nd level or lower) on a target.
  • Sect Influence. Hasan uses his Sect Influence ability to command one of his followers to perform a specific action.
  • Spellcasting. Hasan casts a wizard spell he has prepared, expending a spell slot as normal.

Currently in the World

Hasan Sabbah, a tall and lean figure, exudes an aura of unwavering authority. He is adorned in flowing robes of deep, inky black, which hang loosely from his frame, concealing his movements and intentions. A hood, also in black, obscures much of his face, revealing only piercing, intense eyes that gleam with knowledge and cunning.

As you observe Hasan Sabbah, he is seated in a dimly lit chamber within the fortress of Alamut, surrounded by the intricate scrolls and parchments that are the core of his knowledge. His surroundings are adorned with richly woven tapestries that depict the history of his Order and its influence throughout the lands.

His mood is one of calculated serenity, reflecting the deep contemplation and resolute determination that are the cornerstones of his character. He appears engrossed in the weight of the world’s secrets, pondering the ever-branching paths that he and his assassins must navigate to achieve their cryptic objectives.

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