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Old Man Killahead - AI-generated fantasy Monster

Old Man Killahead

Old Man Killahead is the name villagers give the courteous stranger who appears before a sudden death. Some claim he was once an executioner who took pride in never making a mistake. Others say he is simply the shape fear takes when a community has agreed to forget its crimes. His brass nameplates bear names that cannot be found in any living record.

Monsters
Medium undead · CR 20 · Unique

Old Man Killahead

A legendary headsman whose quiet courtesy makes every encounter feel like a sentence already passed.
AC20
HP285/285
CR20
Init
STR
DEX
CON
INT
WIS
CHA
ConditionsNone

Combat

AC 20 · HP 285 · CR 20

Old Man Killahead

Medium undead (custom supernatural executioner), neutral evil
Armor Class20 (scarred executioner's coat)
Hit Points285 (30d8 + 150)
Speed
30 ft.
STR
DEX
CON
INT
WIS
CHA
Saving ThrowsStrengthConstitutionWisdomCharisma
SkillsInsightIntimidationPerceptionStealth
Damage Resistances
bludgeoning, piercing, and slashing from nonmagical attacks
Immunities
frightened
Weaknesses
Old Man Killahead has no special vulnerability to a damage type.
Speaking the name of one of his forgotten victims aloud within 30 feet gives that victim's allies advantage on their next saving throw against The Headcount before the end of their next turn.
Senses
Truesight 60 ft.,
Passive Perception 20
Languages
Common,
understands all languages but speaks only in Common
Challenge20
Proficiency Bonus+6
Initiative+5
Passive Perception20
Legendary Resistance (3/Day). If Old Man Killahead fails a saving throw, he can choose to succeed instead. He can use this trait three times per day.
Magic Resistance. Old Man Killahead has advantage on saving throws against spells and other magical effects.
Unnatural Tools. Old Man Killahead's weapon attacks are magical.
A Clean Sentence. A creature reduced to 0 hit points by Old Man Killahead's Make an Example attack dies if it is a creature that can be decapitated. This effect does not apply to a creature with legendary actions or a player character unless the DM has established that instant death is appropriate. A creature killed this way can be restored to life by magic that does not require its head to be intact.

Actions

Multiattack. Old Man Killahead makes three attacks: two with his Cleaver and one with his Hook, or three with his Cleaver.
Cleaver. Melee Weapon Attack: to hit, reach 10 ft., one target. Hit: 25 () slashing damage. If the target is a creature, it must succeed on a Strength saving throw or be pulled up to 10 feet toward Old Man Killahead.
Butcher's Hook. Melee Weapon Attack: to hit, reach 15 ft., one target. Hit: 22 () piercing damage, and the target is grappled (escape ) if it is Large or smaller. Until this grapple ends, the target is restrained. Old Man Killahead can grapple only one creature with his Hook at a time.
The Headcount (Recharge 5-6). Old Man Killahead chooses up to three creatures he can see within 60 feet. Each target must make a Wisdom saving throw. On a failure, a target takes 36 () psychic damage and is frightened until the end of its next turn. On a success, it takes half damage and is not frightened. A creature that fails this save by 5 or more is also stunned until the end of its next turn. Once used, this action cannot be used again until the start of Old Man Killahead's next turn.
Make an Example. Old Man Killahead makes one Cleaver attack against a creature grappled by his Hook. On a hit, the attack deals an extra 22 () slashing damage. If this damage reduces the target to 0 hit points, Old Man Killahead decapitates it. A creature that does not need a head to live is immune to the decapitation, but still takes the extra damage.

Reactions

No One Leaves. When a creature Old Man Killahead can see within 15 feet moves out of his reach, he makes one Cleaver attack against it. On a hit, the target's speed becomes 0 until the end of the current turn.

Legendary Actions

Slow Step. Old Man Killahead moves up to half his speed without provoking opportunity attacks.
Quick Cut. Old Man Killahead makes one Cleaver attack.
Say Your Name (costs 2 actions). One creature Old Man Killahead can see within 30 feet must succeed on a Wisdom saving throw or be frightened until the end of its next turn. A creature that succeeds is immune to this effect for 24 hours.
Bring Them Here (costs 3 actions). Old Man Killahead makes one Butcher's Hook attack. If the target is already grappled by him, he may instead use Make an Example.
Role
Solo legendary executioner and control-focused boss
Built for
A party of four or five characters of 17th to 20th level

Gear

  • Cleaver (Weapon, Priceless to collectors; unsettling to handle)A broad, unnaturally sharp cleaver. It counts as a magical weapon.
  • Butcher's Hook (Weapon, Priceless to collectors; each nameplate bears a victim's name)A long butcher's hook with a ring of brass nameplates tied beneath its grip. It counts as a magical weapon.

Notes for the game master

Old Man Killahead is a custom monster designed for D&D 5E, not a canonical published creature.
Legendary Resistance (3/Day): If Old Man Killahead fails a saving throw, he can choose to succeed instead.
Magic Resistance: Old Man Killahead has advantage on saving throws against spells and other magical effects.
He has three legendary action points, regaining all spent points at the start of his turn. He can take one legendary action at a time, at the end of another creature's turn.

Tactics

  1. Opening

    He appears as a harmless old man and lets the party approach. Once they are within reach, he uses The Headcount, then closes on the most isolated or visibly injured target.

  2. Mid-fight

    He uses the Hook to restrain a dangerous melee combatant, then punishes the grappled target. He uses The Headcount when several enemies are clustered or when spellcasters are concentrating.

  3. End of the fight

    If badly wounded, he uses The Headcount to break the party's formation, then hooks a vulnerable target and attempts Make an Example. He fights to the death if cornered, but may offer to let the rest go if one character gives him a name.

  4. Retreat

    Old Man Killahead does not flee while he has a path to a victim. If reduced below 50 hit points with no escape route, he bargains for a name, a head, or a promise that someone will remember him.

How it fights

Use his 10-foot Cleaver reach to punish enemies who assume he is slow or harmless.
Do not spend The Headcount against a single target unless it can set up a decisive attack.
Use his Hook against a healer or controller only when allies can exploit the restrained target.
Use legendary actions to reposition or pressure characters between turns.

Who it attacks first

An isolated character within Hook range
A concentrating spellcaster who can be restrained
A wounded target he can finish with Make an Example
A creature attempting to flee with a victim or nameplate

Works well with

A lair with narrow passages makes his reach and forced movement more threatening.
Minions who block escape routes can create openings for his Hook without adding much damage.
A social scene involving a disputed name or forgotten victim can make The Headcount feel like a consequence of the story.

How to beat it

Keep distance and use forced movement to deny his Hook's reach.
Freedom of movement or similar effects prevent his grapple from restraining a target.
Spread out to limit the number of creatures affected by The Headcount.
His low Dexterity saving throw makes area effects that require Dexterity effective.
Protect concentrating or wounded allies from being isolated.

Ways to avoid a fight

He can trade a victim's name for safe passage, a secret, or the promise that the party will remember someone the world has forgotten.
A nameplate can reveal a missing person's identity or the location of their remains.
He may agree to postpone a sentence if the party proves the accused innocent in a public hearing.

Ecology

A stooped, white-bearded man in a blood-dark apron, with a butcher's hook in one hand and a cleaver broad enough to serve as a door. His face is ordinary until he turns toward someone: then the skin seems stretched too tightly over a skull with no visible eyes. A string of little brass nameplates hangs from his belt.

Behavior

Patient, courteous, and unnervingly attentive. He calls every stranger by a name they have not yet given him. He never raises his voice, even while fighting, and treats violence as a chore that must be finished properly.

How it lives

He needs neither food nor sleep, but he collects the names and heads of those he kills. In places where he lingers, people begin forgetting the faces of the dead while remembering the sound of a cleaver being sharpened.

Lair

His lair is an empty execution chamber where every blade is clean and every chair faces the chopping block. While there, he can manipulate doors, hanging chains, and the room's echoes, but these effects do not deal damage unless stated by the DM.

Habitat
Abandoned villages, old gallows, slaughterhouses, ruined courts, and roads where travelers vanish without a struggle.

Signs that it is near

A clean, crescent-shaped cut in a door or table, always at neck height.
Brass nameplates found in places where no one remembers the dead.
The smell of soap and iron, with no blood visible.

Tags

boss,
legendary,
horror,
executioner,
custom monster

Lore

Old Man Killahead is the name villagers give the courteous stranger who appears before a sudden death. Some claim he was once an executioner who took pride in never making a mistake. Others say he is simply the shape fear takes when a community has agreed to forget its crimes. His brass nameplates bear names that cannot be found in any living record.

What drives it

To make every death feel inevitable and every forgotten victim remembered, if only by him.

After the fight

When Old Man Killahead dies, his tools fall silent and the heads he has kept begin whispering their owners' names. The heads can be laid to rest by returning them to their families or burying them beneath a tree planted in their memory.

“Some claim he was once an executioner who took pride in never making a mistake.”
From its lore

Variants

The Kindly Neighbor: A version who offers food and shelter before asking each guest to state their name.
The Court's Old Clerk: A version who marks names in a ledger and uses legal records instead of brass nameplates.

Hooks

Plot hooks

A village's memorial lists fewer dead each morning, while the families insist someone is missing.
A brass nameplate bearing a party member's name appears on a hook in a locked room.
An old executioner's records prove that a celebrated local hero was convicted on fabricated evidence.

How to use it

A solo boss in a cramped slaughterhouse, abandoned courthouse, or village square at dusk.
A final adversary whose victims have been erased from local records and family memories.
A social encounter first: the party may meet him as a kindly old man who offers directions or a meal.

Treasure

The cleaver and hook, which count as magical weapons but become mundane if Old Man Killahead is dead for one year.
Brass nameplates containing the identities of forgotten victims.
A ledger whose entries change to record the names of those who have died nearby.

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