Way of the Gambler

Playing as a Way of the Gambler monk offers a dynamic and unpredictable experience. Players will need to make tactical decisions on when to take risks, using their luck points to create advantageous situations for themselves and their allies. This subclass combines agility and cunning, rewarding creative strategies while keeping opponents guessing about the next big gamble.

Roll of Fate

At 3rd level, you can roll a d6 at the start of your turn as a bonus action, risking fate. Depending on the outcome, you gain one of the following benefits or drawbacks until the start of your next turn.

• 1: Unlucky – You suffer disadvantage on your next attack roll or saving throw. Additionally, if you fail the roll, you take psychic damage equal to your Monk level.
• 2-3: Break Even – No effect, but you can choose to roll again by spending 1 ki point, taking the new result.
• 4-5: Lucky Strike – You gain advantage on your next attack roll or saving throw. If you hit or succeed, the target takes additional damage equal to your Wisdom modifier.
• 6: Jack of All Trades – You gain a bonus action that can be used to make one unarmed strike or use a ki feature without spending ki. In addition, you can roll the d6 again on your next turn as a free action.

Gambler's Luck

Starting at 6th level, you can push the odds further in your favor. When you spend ki points to use Flurry of Blows, Patient Defense, or Step of the Wind, you can gamble by rolling a d6:

• On a roll of 4-6, you regain 1 ki point.
• On a roll of 1-3, you take damage equal to the roll result.

Additionally, you can now spend 2 ki points to reroll one attack roll, damage roll, or ability check.

Stakes of Fate
At 6th level, you can wager ki to gain advantage in the midst of combat. As a reaction when you are hit by an attack, you can spend 2 ki points to force the attacker to reroll the attack, potentially making them miss. If the reroll results in a hit, you take additional damage equal to your Monk level.

Double or Nothing: When you take the Attack action, you can choose to make one of your attacks with disadvantage. If that attack hits, you can roll an additional Martial Arts die for damage and gain an additional action to use for an attack or another ability on your turn. If it misses, you cannot make any further attacks that turn.

Stakes of Fate

At 6th level, you can wager ki to gain advantage in the midst of combat. As a reaction when you are hit by an attack, you can spend 2 ki points to force the attacker to reroll the attack, potentially making them miss. If the reroll results in a hit, you take additional damage equal to your Monk level.

All-In

At 11th level, you can push your luck even further. As an action, you can spend 3 ki points to roll a d6. Depending on the outcome, you gain the following effects for 1 minute:

• 1: Bust – Your speed is halved, you have disadvantage on all attack rolls and saving throws, and you cannot spend ki for the duration.
• 2-3: Double Down – Your next attack deals an extra 2d6 damage, but you take 2d6 psychic damage. Additionally, if your next attack misses, you take an additional 2d6 psychic damage.
• 4-5: Hot Streak – You gain advantage on all attack rolls, and your movement speed increases by 20 feet. In addition, if you hit twice in the same round, you can make one more unarmed strike as part of that same attack action.
• 6: Jackpot – You regain ki points equal to your proficiency bonus and gain resistance to all damage for the duration. Additionally, you can take an additional action on each of your turns during the duration (similar to Haste), though you don’t suffer the lethargy after the effect ends.

Gamble of the Immortal

At 17th level, you can enter a heightened state of fortune. As an action, you can roll a d20 and gamble your life essence. If you roll a 10 or higher on the d20, you can now choose two effects from the list:

• • Regain all expended ki points.
  • Advantage on all attack rolls, saving throws, and ability checks.
  • Additional 3d10 force damage on unarmed strikes.
  • Gain immunity to one damage type of your choice for the duration.
  • At the end of each of your turns, roll a d6. On a 4-6, you regain ki points equal to half your Wisdom modifier (rounded up).

• If you roll a 9 or lower, in addition to having your hit point maximum reduced by half for 24 hours and being unable to regain hit points, you also have disadvantage on all saving throws for the next hour.

Ultimate Gambit: You can spend all your remaining luck points to double the damage dice of a critical hit. You can treat any attack roll of 16 or higher as a critical hit for that attack. This ability can only be used once per long rest.

Fortune's Blessing: When you roll for initiative, if you have at least 1 luck point, you may choose to regain 1d4 luck points. Additionally, when you score a critical hit, you can grant yourself or an ally an additional action on their next turn, which can only be used for an attack.

Loaded Dice

Starting at 13th level, you gain the ability to manipulate your chances. When rolling any dice as part of a Monk feature (such as Roll of Fate or All-In), you can spend 1 ki point to reroll any dice roll. You can use this feature a number of times equal to your Wisdom modifier per long rest.

Additionally, when you use Roll of Fate or All-In, you can choose to roll two dice instead of one, taking the higher or lower result depending on your preference. However, if you take the lower result, you regain 1 ki point.

Master of Fate

At 17th level, you can manipulate fate itself to the highest degree. When using any Monk feature that requires a dice roll, you can choose to roll with advantage or disadvantage (your choice) without spending ki points. Additionally, when you roll a 6 on Roll of Fate, you automatically gain the benefit of the Jackpot result from All-In.

Once per long rest, you can also choose to completely reroll the result of Gamble of the Immortal, taking the new result regardless of the outcome.

Gambler's Boon

At 5th level, you gain access to a set of abilities that reflect your growing control over fate and chance. Choose one of the following Gambler’s Boons:

1. Risk Taker’s Flow

Whenever you use Flurry of Blows, you can roll a d6. On a 4-6, you gain an extra unarmed strike as part of the same Flurry of Blows action. On a roll of 1-3, you take psychic damage equal to half your Monk level, but you can spend a luck point to negate this damage.

• At 11th Level: If you roll a 4-6, the extra unarmed strike deals an additional damage die (your Martial Arts die). If you roll a 1-3, you take psychic damage equal to your full Monk level instead. You can spend a luck point to regain hit points equal to your Wisdom modifier.

• At 17th Level: If you roll a 6, you can make a third unarmed strike as a bonus action, and all strikes during the Flurry gain a +1 bonus to damage rolls. If you hit with all attacks, you regain a number of luck points equal to your proficiency bonus.

2. Lucky Dodge

You learn to evade danger with a gambler's instinct. When you use Patient Defense, you can roll a d6. On a 4-6, you take no damage from the next attack that hits you before your next turn and regain temporary hit points equal to your Monk level. On a roll of 1-3, you take no damage, but you have disadvantage on your next saving throw.

• At 11th Level: On a roll of 4-6, you can impose disadvantage on the next attack roll made against you, and if it misses, you regain hit points equal to your Wisdom modifier. You can also spend a luck point to gain advantage on your next attack roll.

• At 17th Level: When you use Patient Defense, you can choose to avoid all damage from the first attack that hits you and immediately make one unarmed strike against the attacker as a reaction. If you hit, you can spend a luck point to deal an additional 2d6 damage.

3. Fortunate Striker

Your attacks strike harder when fortune favors you. When you hit with an unarmed strike, you can roll a d6. On a 4-6, you add an additional Martial Arts die to the damage roll. On a 1-3, you deal normal damage but are knocked prone at the end of your turn due to overextending.

• At 11th Level: On a roll of 4-6, you may roll an additional die (up to 2) to the damage roll, and you regain hit points equal to your Wisdom modifier on a successful hit. On a 1-3, you deal normal damage but are stunned until the end of your next turn. You can spend a luck point to reroll the damage dice.

• At 17th Level: If you roll a 6, you can choose to maximize your damage instead of rolling. Additionally, you may impose disadvantage on the target’s next attack roll against you. You can spend a luck point to ignore the prone condition when overextending.

Fortunate Striker

Your attacks strike harder when fortune favors you. When you hit with an unarmed strike, you can roll a d6. On a 4-6, you add an additional Martial Arts die to the damage roll. On a 1-3, you deal normal damage but are knocked prone at the end of your turn due to overextending.

• At 11th Level: On a roll of 4-6, you may roll an additional die (up to 2) to the damage roll, and you regain hit points equal to your Wisdom modifier on a successful hit. On a 1-3, you deal normal damage but are stunned until the end of your next turn. You can spend a luck point to reroll the damage dice.

• At 17th Level: If you roll a 6, you can choose to maximize your damage instead of rolling. Additionally, you may impose disadvantage on the target’s next attack roll against you. You can spend a luck point to ignore the prone condition when overextending.

Lucky Dodge

• You learn to evade danger with a gambler's instinct. When you use Patient Defense, you can roll a d6. On a 4-6, you take no damage from the next attack that hits you before your next turn and regain temporary hit points equal to your Monk level. On a roll of 1-3, you take no damage, but you have disadvantage on your next saving throw.

  • At 11th Level: On a roll of 4-6, you can impose disadvantage on the next attack roll made against you, and if it misses, you regain hit points equal to your Wisdom modifier. You can also spend a luck point to gain advantage on your next attack roll.

  • At 17th Level: When you use Patient Defense, you can choose to avoid all damage from the first attack that hits you and immediately make one unarmed strike against the attacker as a reaction. If you hit, you can spend a luck point to deal an additional 2d6 damage.

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Risk Taker's Flow

Whenever you use Flurry of Blows, you can roll a d6. On a 4-6, you gain an extra unarmed strike as part of the same Flurry of Blows action. On a roll of 1-3, you take psychic damage equal to half your Monk level, but you can spend a luck point to negate this damage.

• At 11th Level: If you roll a 4-6, the extra unarmed strike deals an additional damage die (your Martial Arts die). If you roll a 1-3, you take psychic damage equal to your full Monk level instead. You can spend a luck point to regain hit points equal to your Wisdom modifier.

• At 17th Level: If you roll a 6, you can make a third unarmed strike as a bonus action, and all strikes during the Flurry gain a +1 bonus to damage rolls. If you hit with all attacks, you regain a number of luck points equal to your proficiency bonus.

 

Fortune's Favor

At 15th level, your control over fate allows you to pick one major boon from the following list. Choose one of the following Fortune’s Favor abilities:

1. Eyes of the Dealer

You can see fate itself unfolding around you. When you roll any die, you may spend 2 luck points to see the result before deciding to take it or not. You may choose to reroll, but must accept the second result. Additionally, you gain Blindsight out to a range of 15 feet, allowing you to sense your enemies' movements even if you can’t see them.

• At 17th Level: When you use this feature, you can choose to reroll a second time, and if you roll a natural 20, you can regain a number of luck points equal to your proficiency bonus. You also gain advantage on Wisdom (Perception) checks.

2. Destiny’s Gambit

Your ki surges with each risk you take. Whenever you use a Monk feature that requires spending ki points, you can roll a d6. On a 4-6, you regain 2 ki points. On a 1-3, your ki points are not restored, but you can deal an additional 2d6 damage to one creature within 10 feet as chaotic energy bursts from you. You can use this additional damage only once per round.

• At 17th Level: Whenever you drop to 0 hit points, you can roll a d20. On a 10 or higher, you are restored to 1 hit point and immediately regain 4 ki points. If you roll a natural 20, you may make one unarmed strike against a creature within your reach as part of this effect. You can spend a luck point to reroll the d20.

3. Stroke of Luck

You’ve mastered the art of manipulating chance. As a bonus action, you can call upon pure luck to influence your next move. Roll a d10 and apply one of the following benefits based on the result:

• At 15th Level:

  • 1-3: You regain 3 ki points and deal an extra 3d6 damage with your next attack.
  • 4-6: You gain advantage on all attack rolls and saving throws until the start of your next turn, and your next attack deals an extra 1d10 damage.
  • 7-9: You gain resistance to all damage until the end of your next turn, and any damage dealt against you is halved.
  • 10: You gain all three effects listed above for the next 3 rounds, and you regain 1 ki point at the end of each of your turns during this effect.

• At 17th Level: You can choose to reroll the d10 and apply the new result, but you must take the second result regardless. Additionally, on a roll of 10, you can regain all expended luck points.

Destiny's Gambit

Your ki surges with each risk you take. Whenever you use a Monk feature that requires spending ki points, you can roll a d6: [roll]1d6[/roll]

• On a 4-6, you regain 2 ki points.
• On a 1-3, your ki points are not restored, but you can choose to deal an additional 2d6 damage to one creature within 10 feet as a surge of chaotic energy bursts from you. You can use this additional damage only once per round.

Additionally, whenever you drop to 0 hit points, you can roll a d20. On a 10 or higher, you are restored to 1 hit point and immediately regain 2 ki points. Once you use this feature, you can’t do so again until you finish a long rest.

Eyes of the Dealer

You can see fate itself unfolding around you. When you roll any die, you may spend 2 luck points to see the result before deciding to take it or not. You may choose to reroll, but must accept the second result. Additionally, you gain Blindsight out to a range of 15 feet, allowing you to sense your enemies' movements even if you can’t see them.

• At 17th Level: When you use this feature, you can choose to reroll a second time, and if you roll a natural 20, you can regain a number of luck points equal to your proficiency bonus. You also gain advantage on Wisdom (Perception) checks.

Stroke of Luck

You’ve mastered the art of manipulating chance. As a bonus action, you can call upon pure luck to influence your next move. Roll a d10 and apply one of the following benefits based on the result: [roll]1d10[/roll]

• 1-3: You regain 3 ki points and deal an extra 3d6 damage with your next attack.
• 4-6: You gain advantage on all attack rolls and saving throws until the start of your next turn.
• 7-9: You gain resistance to all damage until the end of your next turn.
• 10: You gain all three effects listed above for the next 3 rounds.

Once you use this feature, you can’t use it again until you finish a long rest.

Luck Points

Starting at 3rd level, you gain a pool of luck points that you can use to influence rolls. You have a number of luck points equal to your proficiency bonus. You regain all expended luck points when you finish a long rest.

You can spend a luck point to gain one of the following benefits:

• Reroll: Reroll an attack roll, ability check, or saving throw. You must use the new roll.
• Alter Fate: When another creature makes an attack roll against you, you can use a luck point to impose disadvantage on the attack roll.
• Lucky Strike: After rolling damage for an unarmed strike or monk weapon attack, you can spend a luck point to add an additional die of damage to the roll.

Wheel of Fortune

Wheel of Fortune: As an action, you can choose to make an attack roll with disadvantage. If you do, you can treat any roll of half your critical hit requirement or higher on the d20 as a critical hit for that attack.

Enhanced Consequence: If your attack is a critical hit, you can roll an additional Martial Arts die for damage. However, if your attack misses, you take psychic damage equal to your monk level, as the gamble weighs on your mind.

• Fortune’s Favor: If you successfully score a critical hit using this ability, you can grant yourself or an ally within 30 feet one of the following benefits:

  • Advantage on their next attack roll.
  • Temporary hit points equal to your Wisdom modifier.

Gambler's Intuition

• Lucky Charm: You gain proficiency in one skill of your choice from the following: Deception, Persuasion, Insight, or Sleight of Hand. If you are already proficient in the chosen skill, you can add double your proficiency bonus to checks made with that skill.
• Cunning Roll: When making an ability check, you can spend 1 luck point to roll an additional d20 and choose which result to use.