Rogue
Base Class: Rogue

"Fortune favors the bold"
Gambler rogues are individuals who's attuned to the fundamental chaos of the world, magic runs through their system as often as alcohol does, and fortune finds them as often as it abandons them. Either failed sorcerers who could not manifest their magic properly or those who shook the hand of some powerful entity for another shot, gambler rogues often start at the bottom with nothing to lose and everything to gain.

All or Nothing

You've dance with fate daily, though that doesn't mean she is any less of a cruel mistress to you. You gain proficiency with a gaming set of your choice.

You may flip a coin when you perform a sneak attack but before rolling damage, you call heads or tails before you flip, if you call correctly, you roll double your sneak attack dice, if you call incorrectly sneak attack does 0 damage.

Roulette!

Whenever you use All or nothing, may choose to roll the roulette. You call red or black then roll a d10, consult the Roulette table for what random effect is won.

If the effect requires a saving throw, the DC equals 8 + your proficiency bonus + your Charisma modifier.

d10 Effect
1 Debt Collector:
Your target thinks you owe them... How much? Well, a lot more than what you have no matter how high you stack your coins, they have disadvantage on attacks against other creatures and advantage on attacks against you! If you called red, they do not get advantage.
2 Snake Eyes
A serpentine glare finds itself staring at the target of your sneak attack, if they can see they must roll a wisdom save or be frightened of you until the end of their next turn. If you call black creatures of your choice within 15 feet of the target are also subjected to the effect.
3 Mid Round Crisis
You are elated with a zeal for life!... Only to come crashing down, you put under the effects of the haste spell for 2 turns. If you call red, you do not suffer the lethargy after the effect ends.
4 Take a Shot:
The alcohol content of your weapon skyrockets as it was injected into your target! Your target gets lightly buzzed and agitated. If you called black they must use their reaction to make an attack against a random creature within their range at disadvantage.
5 Big Win:
Jackpot! You won! Illusory gold and platinum start spilling out of your mouth or any available exit to your body if you do not have one. If you called red creatures of your choice within 60 feet of you must make a wisdom or intelligence saving throw (Their choice) or else, they must use their reaction to move towards you up to their movement and fall prone as they dive at the floor to scoop up the gold their pupils now having golden G's in the middle.
6 I can stop whenever I want:
That was a high roll on the roulette! Just one more and surely, you'll get a better result just one more... Maybe one more... Another surely won't hurt! For the next minute, your sneak attacks trigger a roulette roll not needing to All or Nothing to trigger it. If you called black you may choose if a sneak attack triggers a roulette roll instead of being forced to roll
7 Drinks on me:
lovely alcoholic drinks with a twisty straw appears near you, the drink is whatever the creature's it was made for's favorite is, You and you and willing creatures within 30 feet of you heal for d8s equal to your proficiency bonus. If you called red the range is doubled and it is instead creatures of your choice
8 That guy said your mother was...:
Your target hears a voice in their head that says somebody insulted their mother! They must make a wisdom save or use their reaction to move up to a random creature up to their movement speed, if they are within melee range, they make a melee weapon attack as part of the same reaction. If you called black the random creature cannot be you.
9 Unlucky: 
Aw shucks! Fortune doesn't smile upon you today, you take d8s damage up to your proficiency as a random coincidence hurts you badly you the DM decides the damage type and what this event is. If you called red creatures within 5 feet of you must make a dexterity saving throw or be subjected to the same effects
10

The house always wins:
Reroll the roulette table. If you called black, you may choose if you called the roll right or wrong on what effect you rerolled.

Pocket Aces

When you miss an attack, fail a saving throw or a skill check, you may roll a d20 and use that result instead. If that result is a 1 you instead take 5d10 psychic damage that cannot be reduced by any way, and automatically fail or miss. Each time Pocket aces is used the automatic failure threshold is increased by 5. After you long rest, the failure threshold is set back to 1

Lucky Coins

You get two lucky coins every long rest, you may spend one to use one of the following festures.
○ When you use all or nothing you flip 2 coins instead
○ After rolling for roulette you may reroll that result
○ You roll Pocket Aces with advantage

Poker Face

You've lied cheated and stole your way to victory more than once, twice or three times.  You gain advantage on deception and sleight of hand checks if you are making the check against a non-hostile creature.

JACKPOT

Once every time you long rest, when you make a successful call from all or nothing, you roll maximum damage on your sneak attack. (edited)

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