Way of the Gambler

Monks of the Way of the Gambler reject the rigid order of traditional monasteries. They embrace the unpredictability of fate, turning luck itself into a weapon. Their ki flows through tools of chance such as cards, coins, and dice, which become extensions of their will. To these monks, battle is a wager, and every strike carries the thrill of risk. With a single stroke of fortune, defeat can become victory.

Level 3: Gambler’s Guile

When you choose this tradition at 3rd level, your ki infuses you with the daring presence and magnetic charm of legendary gamblers.

• You gain a bonus to all Charisma ability checks equal to your Wisdom modifier (minimum of +1).
• You gain proficiency with one type of gaming set of your choice, and in one of the following skills of your choice: Deception, Performance, or Persuasion.

Additionally, you learn the prestidigitation cantrip. Wisdom is your spellcasting ability for this spell.

Level 3: Gambler's Wit

Also at 3rd level, your experience with games of chance sharpens your eye for opportunity and weakness.

• Your unarmed strikes and monk weapons score a critical hit on a roll of 19 or 20 on the d20.

• You have advantage on ability checks made to gamble, place or resolve bets, negotiate contracts, attempt bribes, or haggle over prices.

Level 6: Double or Nothing

Starting at 6th level, you bind your fate ever more tightly to chance itself. When you score a critical hit with an Unarmed Strike or Monk weapon, right before you roll for damage, you can spend 1 ki point to tempt fate. Roll your Martial Arts Die. If you roll a 6 or higher, you roll four times the normal number of dice for the damage, instead of twice as many. If you roll a 5 or lower, the attack is treated as a normal hit rather than a critical hit.

Level 11: All In

Your willingness to wager everything makes every strike more volatile. At 11th level, your Unarmed Strikes and attacks with Monk weapons score a critical hit on a roll of 18, 19, or 20 on the d20, but automatically miss on a roll of 1 or 2.

At 17th level, your Unarmed Strikes and attacks with Monk weapons score a critical hit on a roll of 17, 18, 19, or 20 on the d20, but automatically miss on a roll of 1, 2 or 3.

Level 11: Jackpot

At 11th level, your willingness to wager everything makes every strike more volatile… and more rewarding.

When you roll the Martial Arts Dice for the damage of a successful Double or Nothing with an Unarmed Strike or Monk weapon, if two or more of those dice show the same number, you regain an amount of Ki points equal to that number. You can regain Ki from this feature 3 times per Long Rest, and only once per turn.

Level 17: The House Always Wins

At 17th level, you learn to subtly rig destiny itself. As an action, you can spend 5 ki points to manipulate the flow of fortune around you. Choose a number of creatures you can see within 30 feet of you, up to your Wisdom modifier (minimum of one). You imbue them with one of the following effects for 1 minute:

Blessed Fortune. Once on each of its turns, a creature can reroll one attack roll, ability check, or saving throw it fails and must use the new roll.

Cursed Fortune. Once on each of its turns, a creature must reroll the first attack roll, ability check, or saving throw it succeeds and must use the new roll.

This manipulation of fate is so subtle that the affected creatures do not perceive its source. You can have only one instance of this feature active at a time.