Gambler

Fortune's favorite children, gamblers are cunning players who live by the philosophy of high risk, high reward. Fate has reserved a special place for gamblers in life, allowing them to gain more critical hits, imbue their gaming sets with magical properties, and bend circumstances to their benefit. Sometimes, however, their luck fails them and the consequences can be less than fortuituous. But gamblers always have an ace up their sleeves...
Compared to other classes, gamblers gain more attacks and subclass features, but less ability score improvements. This is balanced by their ability to add a Luck modifier to any attack roll, saving throw or skill check they make. You can play a gambler as an agile striker or utility supporter.

The Gambler

Level - Profiency Bonus - Features

1. +2 - Gambler's Luck, Playstyle, Weapon Mastery
2. +2 - Resourceful
3. +2 - Expertise
4. +2 - Ability Score Improvement
5. +3 - Extra Attack
6. +3 - Playstyle Feature
7. +3 - Evasion
8. +3 - Bribery
9. +4 - Lucky Streak
10. +4 - Ability Score Improvement
11. +4 - Playstyle Feature
12. +4 - Assessment
13. +5 - Coin Flip
14. +5 - Extra Attack (2)
15. +5 - Playstyle Feature
16. +5 - Ability Score Improvement
17. +6 - Poker Face
18. +6 - Sharp Mind
19. +6 - Playstyle Feature
20. +6 - Fortune's Favorite

Quick Build

You can make a gambler quickly by following these suggestions. First, put your highest ability in Dexterity, followed by Constitution. Second, choose the Rewarded background.

Class Features

As a gambler, you gain the following class features.

Hit Points

Hit Dice: 1d10 per gambler level

Hit Points at 1st level: 10 + your Constitution modifier

Hit Points at Higher Levels: 1d10 (or 6) + your Constitution modifier per gambler level above 1st

Proficiencies

Armor: light armor, shields

Weapons: simple weapons, firearms, cane swords, hand crossbows, rapiers, sawblade bowler hats, shortswords

Tools: all gaming sets

Saving Throws: Dexterity, Intelligence

Skills: choose three from Deception, Insight, Investigation, Perception, Sleight of Hand and Stealth

Equipment

You start with the following equipment, in addition to the equipment granted by your background.

(a) a pistol and 20 bullets, (b) a rapier, or (c) any simple weapon

(a) a diplomat's pack or (b) an explorer's pack

(a) playing cards gaming set or (b) dice gaming set

leather armor and a dagger

Multiclass Prerequisites:

Minimum Skill Requirements: Dexterity 13

Proficiencies Gained: light armor, one skill from the class's skill list, all gaming sets

Gambler's Luck

Gamblers are discerned from other classes by their seventh ability score, Luck. Unlike the other abilities, however, your Luck ability score is always fluctuating. Whenever you are about to roll a d20 to make an attack roll, saving throw or skill check, you can choose to add your Luck modifier to the roll. You must make the decision before making the roll. You then roll two d20 (hint: use different colored dice), one of which determines your modifier for your roll.

1: -5

2-3: -4

4-5: -3

6-7: -2

8-9: -1

10-11: 0

12-13: +1

14-15: +2

16-17: +3

18-19: +4

20: +5

If you roll the same natural number on both d20s, regardless of the modifiers, you can choose to roll both of them again. An exception to this is when making attack rolls with the Luck modifier: if you roll a natural 20 on both dice, you can roll all your damage dice three times for the attack, but if you roll a natural 1 on both dice, you may not re-roll and the damage is directed to yourself instead.
If you have advantage or disadvantage to your d20 roll, you only roll for the Luck modifier once, and compare the number with the higher or lower result, whichever is applied.

Playstyle

At 1st level, you choose one playstyle related to your gaming set of choice: Card Shark (playing card set), Fortune Teller (any set), High Roller (dice set) or Tactician (dragonchess set). Each playstyle is detailed at the end of the class description, and they each offer a different specialization to the gambler: Card Shark uses elemental cards and a limited amount of spellcasting, Fortune Teller can use their Luck modifier to affect allies and enemies as well, High Roller strongarms their way to victory with loaded dice, and Tactician boosts their allies while they are in formations.
Your playstyle choice grants you features at 1st level and again at 6th, 11th, 15th and 19th levels.

Weapon Mastery

Also at 1st level, you can choose two Weapon Masteries based on weapons you are proficient in. You can use these mastery features each time you make a weapon attack with the related weapon. You can change one of these masteries to another valid to you after you finish a long rest.

Resourceful

Starting at 2nd level, you can take the Disengage and Help actions as a bonus action.

Expertise

At 3rd level, choose two of your skill proficiencies, or one of your skill proficiencies and your proficiency in all gaming sets. Your proficiency bonus is doubled for any ability check you make that uses either of the chosen proficiencies.

Ability Score Improvement

When you reach 4th level, and again at 10th and 16th level, you can increase one ability score of your choice by 2, or you can increase two ability scores of your choice by 1. As normal, you can't increase an ability score above 20 using this feature. You can't affect your Luck ability score with this feature.
If your DM allows the use of feats, you may instead take a feat.

Extra Attack

Beginning at 5th level, you can attack twice, instead of once, whenever you take the Attack action on your turn. The number of attacks increases to three when you reach 14th level in this class.

Evasion

Beginning at 7th level, because of extraordinary good luck, you are skilled at avoiding danger. When you are subjected to an effect that allows you to make a Dexterity saving throw to take only half damage, you instead take no damage if you succeed on the saving throw, and only half damage if you fail.

Bribery

At 8th level, you are ensured to be able to bribe your way out of sticky situations. Whenever you would make a Charisma skill check against a creature that you can see and reach and that can understand you, you can pay gold to automatically succeed on the check. The amount of gold you have to pay depends on the Difficulty Class (DC) of the check:

DC 5: 1 gold

DC 10: 10 gold

DC 15: 100 gold

DC 20: 1000 gold

DC 25: 10.000 gold

DC 30 or above: cannot be bribed

At your DM's discretion, you can also use items of equal value in gold for the bribery.

Lucky Streak

At 9th level, you can experience short streaks of luck. Whenever you make a Luck modifier roll, you can choose to keep the resulting modifier for 1 minute, applying it to all of your attack rolls, saving throws and skill checks. If the roll was a natural 20, you can apply it to all critical hits made during that time to triple your damage dice, as depicted in your Gambler's Luck feature. The streak ends early if you decide to roll your Luck modifier again. Once you've used this feature, you cannot use it again until you finish a long rest.

Assessment

Beginning at 12th level, you can try to discern information about a creature you can see within 60 ft. of you as an action. The creature makes a contested Deception (Charisma) or Stealth (Dexterity) check against your Insight (Wisdom) or Investigation (Intelligence) check. If you win the contested check, you learn certain information about the creature: all of its proficiencies, its Armor Class, and its Speed. If you lose the contested check, you cannot use this feature on the same creature or creatures that share its statblock again until you finish a long rest.

Coin Flip

At 13th level, you gain a 50-50 chance to make your attack either a critical hit or an automatic miss. When you make an attack on your turn, you can decide to forgo rolling a d20 and roll a d2 (or flip a coin) instead and guess the result (1 or 2, or heads or tails). If you guessed correctly, the attack is an automatic critical hit. If you guessed incorrectly, the attack fails. You can use this feature a number of times equal to your proficiency modifier, and regain all uses after finishing a long rest.

Poker Face

By 17th level, you have developed nerves of steel and remain calm in any situations. You are immune to becoming charmed or frightened. Furthermore, other creatures automatically fail any insight or intimidation checks made against you.

Sharp Mind

At 18th level, your cunning mind can prepare for any possible outcome. You gain proficiency in Wisdom and Charisma saving throws.

Fortune's Favorite

Finally at 20th level, once per day, you can invoke your good graces with fate and fortune, and choose the result of any d20 roll you make before you roll it, including your Luck modifier roll.
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Card Shark Features

This gambler playstyle features uses a playing card set. If you ever lose access to that set, you must acquire a new one before the features can be used again.

1st: Magic Playing Cards, Cartomancy (1st level)

6th: Cartomancy (2nd level), Hand of Fate (Jokers)

11th: Cartomancy (3rd level), Hand of Fate (Jacks)

15th: Cartomancy (4th level), Hand of Fate (Queens)

19th: Cartomancy (5th level), Hand of Fate (Kings)

Magic Playing Cards

When you choose this playstyle at 1st level, you gain access to an enchanted deck of playing cards. You can use these cards as a weapon during combat, they use your gaming set proficiency, and they are considered magical for the purpose of overcoming resistance and immunity to nonmagical attacks and damage.
The cards have the finesse, hidden, light and thrown (range 20/60) properties. When you are about to make an attack, you draw five cards from the deck to your hand and choose which card to attack with. Damage caused by the cards is calculated by the suit (damage type) and value of the card (amount of damage), adding your attack ability modifier to the value.

Clubs (or Staves): thunder damage

Diamonds (or Pentacles): cold damage

Hearts (or Chalices): fire damage

Spades (or Swords): lightning damage

After you attack with a card, it magically returns shuffled into your deck. When your hand is empty, you draw back to five. All cards return to your deck after 1 minute of not being used to attack, or when you choose so (no action required).
You can use a standard deck of playing cards with four suits and values 1-10 (set the Jokers, Jacks, Queens, Kings aside for the Hand of Fate feature). Optionally, you can throw 5d4 to determine the suit and 5d10 to determine the value of the cards in your hand by pairing each d4 to a d10, and repeat the process each time your hand is empty.

Cartomancy

Additionally at 1st level, you can cast one spell through your deck of magic playing cards, which also acts as your spellcasting focus. The level of the spell slot depends on your gambler level, and you always cast spells at the highest level spell slot available to you. You learn additional spells to choose from at higher levels. Once you have cast a spell using this feature, you cannot do so again until you finish a short or a long rest.

Spell Slot - Spells Known

1st level: 1st level spell slot - bane, bless, hex

6th level: 2nd level spell slot - aid, enhance ability, spray of cards

11th level: 3rd level spell slot - bestow curse, counterspell, dispel magic

15th level: 4th level spell slot - banishment, confusion, elemental bane

19th level: 5th level spell slot - bigby's hand, mislead, wall of force

Spellcasting Ability

Dexterity is your spellcasting ability for your cartomancy spells, since you use your hand gestures to connect to the weave of magic.

Spell save DC = 8 + your proficiency bonus + your Dexterity modifier

Spell attack modifier = your profiency bonus + your Dexterity modifier

Hand of Fate

At 6th level, you learn how to influence fate and fortune with the face cards of your deck of magic playing cards. You can play a card from your Hand of Fate as a bonus action to give the desired effect of the card to yourself or to a creature you can see within 60 feet of you.
Once you have used a card from your Hand of Fate, it magically vanishes and cannot be used again until you finish a long rest. After you finish a long rest, you can swap an unused face card to another of the same value. If you use a real deck of playing cards, keep the face cards in a separate deck from the other cards.
At first, you have the two Joker cards at your disposal. You can play a Joker from your Hand of Fate to give advantage or disadvantage to the next attack roll, saving throw or skill check. You always regain both Jokers to your Hand of Fate when you finish a long rest.
The other face cards come into play at higher levels. Starting at 11th level, each time you finish a long rest, you can add a Jack (11) of the suit of your choice to your Hand of Fate. At 15th level, you can also add a Queen (12) of your choice to your Hand of Fate, for a total of four cards. And finally, at 19th level you can add a King (13) of your choice to your Hand of Fate, for a grand total of five cards. The Jacks, Queens and Kings have the following effects depending on their suit:

Clubs (or Staves): Speed decreased or increased by 5 ft. (Jack), 10 ft. (Queen) or 15 ft. (King) for 10 minutes.

Diamonds (or Pentacles): Armor Class decreased or increased by 1 (Jack), 2 (Queen) or 3 (King) for 10 minutes.

Hearts (or Chalices): temporary hit points equal to 1d4 (Jack), 2d4 (Queen) or 3d4 (King) plus your dexterity modifier.

Spades (or Swords): weapon attack and damage rolls decreased or increased by 1 (Jack), 2 (Queen) or 3 (King) for 10 minutes.

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Fortune Teller Features

This gambler playstyle features uses any gaming set. If you ever lose access to a gaming set, you must acquire a new one before the features can be used again.

1st: Diviner's Cantrips, Portents of Fortune

6th: Fortuituous Help, Innate Augury

11th: Shared Streak, Wheel of Fortune

15th: Greater Assessment, Greater Portents of Fortune

19th: Innate Divination, Roulette of Life and Death

Diviner's Cantrips

At 1st level when you first choose this playstyle, you learn the guidance and true strike cantrips.

Portents of Fortune

Also starting at 1st level, you catch glimpses of future events. When you finish a long rest, roll a d20 three times for the Luck modifier in your Gambler's Luck feature, and record the results as your three portent modifiers. You can modify any d20 attack roll, saving throw or skill check made by you or a creature you can see with one of these foretold modifiers. You can wait until after the roll of the d20 before deciding to use a portent modifier, but must decide before the DM says whether the roll succeeds or fails. Each portent modifier can be used only once. When you finish a long rest, you lose any unused portent modifiers.

Fortuituous Help

Beginning at 6th level, whenever you use the Help action or bonus action to aid an ally, the ally may choose to use your Gambler's Luck feature and roll a Luck modifier as part of their attack roll or skill check. Furthermore, when you help an ally in attacking a creature, that target can be up to 30 feet away from you.

Innate Augury

Also at 6th level, you can use your gaming set to cast the augury spell as a ritual without other material components. The answer will be provided by a deity or spirits of fate and fortune.

Shared Streak

Beginning at 11th level, whenever you use the Help action or bonus action to aid an ally, they can use the effects of your ongoing Lucky Streak for their roll as well.

Wheel of Fortune

Also at 11th level, you can spend an action conjure a colorful, magical wheel that gives a multitude of effects to anyone who spin it. You can spin the wheel yourself as part of the same action used to create it. The wheel stays in place until the start of your next turn (but does not occupy a space), and any creature can use an action on their turn to spin it. The wheel cannot be damaged, but it can be dispelled. The wheel has 12 sectors, represented by a roll of a d12:

1. The spinner ends their turn immediately
2. The spinner gains 1 gold.
3. The spinner gains the benefits of the blade ward cantrip until the end of their next turn.
4. The spinner gains the benefits of the blur spell for 1 minute and concentrates on it.
5. The spinner gains the benefits of the mirror image spell for 1 minute.
6. The spinner gains the benefits of the enlarge spell for 1 minute and concentrates on it.
7. The spinner gains the benefits of the haste spell for 1 minute and concentrates on it.
8. The spinner gains the benefits of the greater invisibility spell for 1 minute and concentrates on it.
9. The spinner gains the benefits of the circle of power spell for 10 minutes and concentrates on it.
10. The spinner gains 1000 gold.
11. The spinner gains the benefits of a short rest, and can roll any number of their hit dice to recover hit points immediately.
12. The spinner gains the benefits of a long rest, restoring full health, as well as any spent spell slots and features.

Once you have used this feature, you cannot use it again until you finish a long rest.

Greater Assessment

At 15th level, you can gleam more information from the target of your Assessment feature. You also learn its maximum and current Hit Points, as well as damage and condition resistances, immunities and vulnerabilities.

Greater Portents of Fortune

Also at 15th level, your visions of possible futures intensify and paint a more accurate picture in your mind of what is to come. You roll five d20s for your portent modifiers, rather than three.

Innate Divination

At 19th level, you can use your gaming set to cast the divination spell as a ritual without other material components. The answer will be provided by a deity or spirits of fate and fortune.

Roulette of Life and Death

Also at 19th level, you have learned to play the ultimate game of life and death. As an action after initiative has been rolled, you may roll a d20 as well as the Luck modifier of your Gambler's Luck feature, with the following effects:

All creatures with the same initiative as the roll that have 100 hit points or fewer instantly die, but you can choose whether or not to apply your Luck modifier to the roll after you've seen the result. You can also apply the modifier of your ongoing Lucky Streak instead of rolling for a new modifier.

However, if there are creatures already at 0 hit points or dead at the matching initiative, they are instantly stabilized or resurrected with 1 hit point.

If there are no creatures at the rolled initiative even after applying the modifier, nothing happens.

If the two d20s have the same number on them, you may choose to roll them both again.

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High Roller Features

This gambler playstyle features uses a dice set. If you ever lose access to that set, you must acquire a new one before the features can be used again.

1st: Loaded Dice

6th: Lucky Strikes

11th: Loaded Critical

15th: Double or Nothing

19th: On A Roll

Loaded Dice

At 1st level when you first choose this playstyle, you can use your enchanted dice to affect the outcome of your attacks. Before you make an attack with a weapon you are proficient with, you can choose one of two options:

Take a -5 penalty to the attack roll, and if it hits, you add +5 to your damage roll.

Add a +5 bonus to the attack roll, and if it hits, you deduct -5 from your damage roll.

If you use this feature, you cannot utilize the Gambler's Luck feature to modify your attack roll.

Lucky Strikes

At 6th level, whenever you hit a target with a weapon attack that utilizes the Luck modifier of your Gambler's Luck feature, you can choose to add the same Luck modifier to the damage roll as well.

Loaded Critical

Beginning at 11th level, when you make an attack roll, you treat rolls of natural 1 and 2 as critical misses, and rolls of natural 19 and 20 as critical hits. For the purposes of rolling the same number twice in your Gambler's Luck feature, treat rolls of 1 and 2 as the same number, as well as rolls of 19 and 20. This also applies to your Lucky Streak.

Double or Nothing

Starting at 15th level, whenever you make an attack roll and roll a natural 19 or 20 with either roll utilizing your Gambler's Luck feature, you can choose to re-roll the other d20 in attempt to roll a natural 19 or 20 on it as well. If you fail, the attack misses automatically.
Additionally, when you guess the outcome of your Coin Flip feature correctly, you can attempt to flip the coin again once without expending a use of the feature. If you guess correctly again, you can roll the damage dice of the critical hit a third time and add it to the total. If you guess incorrectly, the whole attack misses.

On A Roll

By 19th level, you have learned to bend fate in your favor. As a reaction, you can re-roll any die rolled by you or another creature you see within 60 feet, but the new roll must be used and cannot be re-rolled again using this or other features. This also applies to the d2 (or coin) of your Coin Flip feature if you guessed incorrectly. You can use this feature a number of times equal to your proficiency bonus, and regain all expended uses when you finish a long rest.

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Tactician Features

This gambler playstyle features uses a dragonchess set. If you ever lose access to that set, you must acquire a new one before the features can be used again.

1st: Shield Formation, Tactical Pawns

6th: Advantageous Formation, Strategic Awareness

11th: Fortuituous Formation (10 feet), Greater Tactical Pawns

15th: Final Gambit, Fortuituous Formation (30 feet)

19th: Fortuituous Formation (60 feet), Supreme Tactical Pawns

Shield Formation

When you choose this playstyle at 1st level, if you have any friendly creatures within 5 feet of you, you and those creatures gain a bonus to Armor Class equal to the number of friendly creatures within range (not counting yourself). The creatures have to be at least small size to be counted in the formation.

Tactical Pawns

Also at 1st level, you become inspired by the various pieces of dragonchess. As an action, you choose one pawn to give certain benefits to yourself or a creature you can touch. Each pawn's effect lasts up to 1 minute. Any spells that are cast as an effect of this feature do not require spell slots or material components.
Once you have chosen a pawn, you cannot choose the same pawn until you finish a long rest, and if you choose another pawn on a creature who still has one in effect, the former effects end. Otherwise you can have several pawns in effect at once. You regain all used pawns when you finish a long rest. You gain more powerful options at Level 11 and even more at Level 19.

Dwarf: the target gains temporary hit points equal to your level plus your proficiency bonus, and resistance to poison damage and the poisoned condition.

Cleric: the target can cast cure wounds at will.

Mage: the target cast chromatic orb at will.

Thief: the target can Dash and Hide as a bonus action.

Sylph: the target's speed increases in feet equal to five times your proficiency bonus, and it gains resistance against the charmed condition and cannot be put to sleep by magic.

Warrior: the target can use its bonus action to attack.

Advantageous Formation

At 6th level, you can use one Help action or bonus action to aid all creatures of your choice within 5 feet of you and give them advantage on their next skill check before the start of your next turn. Alternatively, you can aid all creatures of your choice within 5 feet of you in attacking another creature up to 30 feet away from you, giving them advantage on their next attack until the end of your turn, as long as they do not move away from you before making the attack.

Strategic Awareness

At 6th level, you cannot be surprised while conscious, and cannot be attacked with advantage if the attacker is hiding or invisible.

Greater Tactical Pawns

At 11th level, you gain five more options to choose with the Tactical Pawns feature.

Griffon: a griffon is summoned to an unoccupied space within 5 feet of the target. It is friendly towards the target who can control it as a bonus action and use it as a mount. It vanishes after the effect ends.

Elemental: the target can cast control water, meld into stone and produce flame at will.

Paladin: the target's weapon attacks deal extra 1d8 radiant damage (2d8 if the target is undead), and it becomes immune to the frightened condition.

Hollyphant: any spell of 5th level or below cannot affect the target at all. Any ongoing spell effect is subdued for the duration of this effect.

Unicorn: the target can cast mass healing word and lesser restoration at will.

Fortuituous Formation

Starting at 11th level, whenever your Lucky Streak is active, all creatures of your choice within 10 feet of you can add your Luck modifier to any roll they make. The range of this feature extends to 30 feet at 15th level, and to 60 feet at 19th level.

Final Gambit

At 15th level, when you are reduced to 0 hit points, you can use your reaction to bestow any remaining tactical pawn you have at your disposal on any creature within 60 feet of you.

Supreme Tactical Pawns

At 19th level, you gain four more options to choose with the Tactical Pawns feature.

Basilisk: the target of this effect chooses another creature within 60 feet of them to become affected by the flesh to stone spell, which is cast without material components. The target becomes immune to incapacitated, paralyzed, petrified and stunned conditions while concentrating on the spell.

Dragon: the target gains flying speed equal to double your walking speed and all its weapon attacks cause extra 3d8 damage that can be acid, cold, fire, lightning or poison (their choice).

Hero: the target has advantage on all attacks, skill checks and saving throws.

King: the target gains resistance to all damage types and conditions.