Way of the Gambler

Monks of the Way of the Gambler have learned to let their strength be altered by the whims of the multiverse. By opening their minds, bodies, and souls to the influence of the world around them, they allow themselves to be given more power. However, the world can give and the world can take away, as sometimes these champions of lady luck find themselves on her bad side. 

Those who follow the Way of the Gambler are often free spirits, roaming from town to town, trusting that fate will take them where they need to be. On their ventures, they're known to play the role of the nameless hero, protecting those in need and doing great favors the regions they go too, earning quite gracious rewards. They are also known to gamble most of said rewards away, often in the same town they won them.

The Card Shark's Mark

Starting at 3rd level, you gain proficiency in one of the following skills of your choice: Insight, Deception, or Sleight of Hand. You choose an additional proficiency from this list at 6th and 11th level.

In addition, you gain proficiency in two gaming sets of your choice. 

Chips to Cash

From 3rd level, when you hit with a weapon attack or unarmed strike, you can spend one ki point to increase the weapon's damage by a d6. You can spend additional ki points up to a number equaling your proficiency bonus, adding an additional d6 per ki point you spend.

A Poor Man's Gamble

At 3rd level, you can enter a wager. When making a wager, you make a special ability check called a wager check. The DC for this check is 10 and it isn't tied to any ability score. Succeeding on this check means that you win the wager. You can wager the following things:

• Ki Points: Once per turn at the start of your turn, you can choose to wager any number of ki points up to a maximum number equal to your proficiency bonus. For example, if you are a 5th level Monk with a proficiency bonus of 3, you can wager a maximum of 3 ki points. You cannot make this wager if your ki points equal or exceed your monk level. If you have a number of ki points exceeding your level when you take a long rest, you ki points return to a number equal to your level.
• Damage: When you deal damage to an enemy with a weapon attack or unarmed strike, you can choose to wager any amount of the weapon's damage. For example, you deal 8 damage with an unarmed strike and wager 3 points of that damage. If you win the wager, the attack now does 11 damage. If you wagered all 8 points of damage and lost, you would deal 0 damage. 
• Hit Points: Whenever you regain hit points, you can choose to wager any amount of hit points you gain. 

You can use this feature a number of times equal to your proficiency bonus and regain uses on a short or long rest. 

The Lady's Favor

Starting at 6th level, whenever you fail an ability check that you are proficient in, you can spend 1 ki point to reroll that ability check.

Additionally, when you make a wager check, you can now add your wisdom modifier to your roll.

Dead Man's Hand

From 11th level, whenever you make a death saving throw, you can choose to make a wager check. If you succeed, you regain a number of hit points equal to a number of rolls of your martial arts die equal to half your Monk level and are brought back up to your feat. If you loose fail, you die instantly. You can't wager hit points you regain this way.

King of Games

At 17th level, you gain proficiency with every gaming set. In addition, you can double your proficiency bonus when making checks related to games that you are proficient in.

You gain the ability to enter a gamble with any other willing entity. The gamble can be anything, from a test of strength or wit to a simple card game. You can wager anything you want, from gold pieces to you own soul, as long as each party wagers an item of equal value(as determined by the DM). You can also determine a punishment for the loser, such as being banished to another plane. Whatever the wager or punishment, both parties must agree to the terms of the game. The results of this gamble will be enforced by Lady Luck herself. If the thing being wagered is something is not something that the parties involved can manipulate, such as souls, the transaction will be made immediately, as if through magic. If the thing wagered is a physical item, such as gold pieces, the transaction must be made by the parties in question. If either party fails to meet their end of the bargain or cheats during the gamble, they will be struck with a string of bad luck, which can have dire consequences(as determined by the DM depending on the severity of the original gamble). Once you use this ability, you can't use it again for another 7 long rests.

The damage added by using the Chips to Cash feature increases from d6s to d8s.