Creature Feature (5e): Gamble

The coin flip rules their day. The Gambles wander along, betting on anything and everything. Beneath their smiles and jokes is a sinister overtone: they want these wagers to be dangerous. The more there is to lose, the more exhilarating they find victories. They appear human, dressed as richly as they fancy. The only difference is their strange eyes.

Never trust a roaming stranger with golden eyes. The man in the tavern corner who rolls and rolls a golden coin with faces that always seems to change. The woman who smiles as she seems to lose at cards. You will lose their games. And once you do, you will be offered a game with better odds and far more dire stakes. And you will lose again. 


Medium aberration, chaotic neutral

Armor Class 14
Hit Points 90 (12d10 + 24)
Speed 30 ft.

12 (+1) 18 (+4) 14 (+2) 12 (+1) 18 (+4) 19 (+4)

Saving Throws Dexterity +7, Charisma +7
Skills Deception +7, Insight +7, Sleight of Hand +7
Damage Resistances fire
Condition Immunities charmed, exhaustion, frightened
Languages Common, Celestial, Infernal
Senses darkvision 60 ft.; passive Perception 14
Challenge 8 (3,900 XP)

Special Traits

  • A Gamble’s Smile. A Gamble will never directly fight unless attacked. The first attack any creature makes against a Gamble is made with disadvantage. 
  • Master Cheat. A Gamble has proficiency and advantage on any skill or ability check made to cheat at a game. 
  • Dark Bet. A Gamble can offer a bet to any creature with Intelligence over 6, who is not immune to charm effects or psychic damage, on any game of chance or strategy. The Gamble has the power to make a number of offers:
    • If the Gamble wins: Any Creature who accepted the bet is automatically affected as if by geas, with no saving throw. This effect lasts for 1, 6, or 12 months (determined when the Gamble makes the bet). If the Gamble loses: The Gamble will create a nonmagical object worth 1,000 – 10,000 GP out of thin air (the value of which is decided by the Gamble when making the bet).
    • If the Gamble wins: Any Creature who accepted the bet takes an amount of psychic damage the Gamble decided upon when making the bet, the amount of which can be up to the Gamble’s maximum number of HP. Any creature brought to 0 HP by this damage becomes a Gamble, identical in statistics to a normal Gamble except that their maximum HP is the same as the maximum HP they had in life. This new Gamble has all the creature’s memories but has its personality twisted to that of the chaotic neutral Gambles. Any PC who goes through this process becomes an NPC. If the Gamble loses: The Gamble takes a number of psychic damage equal to an identical amount of damage as previously noted. The Gamble cannot resist this damage in any way. If a Gamble dies in this way, one winning creature gains the ability to cast resurrection once with no spell component, regardless of class or level. If multiple creatures are involved in the bet, they must either unanimously choose a creature to gain this boon or continue to play a game of chance until there is one single decided victor (all of which the creatures are aware of and must decide upon when the bet with the Gamble is originally made). 


  • Multiattack. The Gamble makes three melee attacks.
  • Easy Bet. Melee Weapon Attack: +7 to hit, reach 5 ft., one target. Hit: 6 (1d4 + 4) bludgeoning damage and 4 (2d4) psychic damage. This attack is automatically is made with advantage (disadvantage negates as normal).
  • Hard OddsMelee Weapon Attack: +7 to hit, reach 5 ft., one target. Hit: 20 (7d8 ) psychic damage. This attack is automatically made with disadvantage (advantage negates as normal).


Gambles avoid combat. While they are usually excited by contests and games; direct conflict itself bores them and negates any chance to gain servants or create new Gambles. 

If a Gamble suspects they have a chance to lose a fight, they will flee (usually with geas enthralled servants ordered to guard them working as distractions). 

If a Gamble believes victory is likely, they and any geas servants nearby will strike at the largest or most dangerous enemy first. Generally, Gambles only use their Hard Odds psychic attack on foes that look especially sturdy or when a battle has turned against the Gamble and they cannot flee. 


Some suspect Gambles are a product of the Hells. There is some evidence to this in that they speak Infernal but even the Gambles themselves are not certain. Gambles are daring thrill seekers but largely incurious about their own history or any other academic pursuit. 

Some Gambles operate in groups, running larger schemes than individual Gambles are capable of. This is rare though as individual Gambles tend to be too mercurial to unite for long. Their greatest thrill comes from betting their own lives in exchange for the life force of others in order to make more Gambles and this thrill is diminished when working together. They have a strange sense of fun and their magic a strange sense of rules: they can cheat all they’d like but, if discovered, immediately lose whatever bet it is they have made. 

Gambles rarely stay in one place long enough for their true nature to be exposed. Nobles who learn of such beings in their lands tend to seek their arrest and death, and with good reason. Gambles hurt people and, left unchecked, will turn numerous victims of their games into even more of the dastardly tricksters. 

A Rumor

It’s said there is a golden-eyed fellow named Ajax who will bet a human-sized figure of gold in a strange game of cards. It is an ancient game with ever-changing rules based on things like one’s seat, the gender of the player, and even the phase of the moon. It is so complicated that it can be difficult to tell if he is making it up as he goes. Exactly what he requires for such a bet is unknown: if the man is indeed real, the people losing his bets don’t seem to be speaking up. 

About Quin Callahan

Quin Callahan is a freelance writer and college level English and economics tutor of over four years experience. He has written for a variety of gaming, technology, and economics publications. His favorite animal might be the squid but he is rarely certain.

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