Gambler

Gamblers enjoy taking a chance, backing themselves to take risks in high risk, high reward situations. Gambling rogues are no different. They thrive off the thrill from taking a chance, risking it all for the possibility of having it all. 

Tempting Fate

Starting at 3rd level when you pick this subclass, you can tempt fate. When you make an attack roll, ability check or saving throw, you can give yourself advantage. You can do this after you know the roll but before you know whether it's a success or failure. You may use either of the rolls. However, the immediate next attack roll, ability check or saving throw you make after that must be made at disadvantage, and this feature cannot be used on that roll. 

You can use this feature 2 x your proficiency bonus per long rest. 

Bonus Proficiencies

Also at 3rd level, you become Proficient in Deception if you’re not already. You gain proficiency in two gaming sets of your choice. 

Gambler’s Instincts

Starting at 6th level, you’re instincts are natural when it comes to reading people. As a bonus action, you can make a contested Insight Check against your targets Deception Check. If they fail, you can find out two from their HP, Armour Class, Strength, Constitution or Dexterity Score. However, if they succeed, they find out two of their choice about you. 

You can use this feature twice per long rest. 

Expect the Unexpected

Starting at 9th level, you’ve come to expect anything. You cannot be surprised, and you can add your intelligence modifier to your initiative bonus. 

Furthermore when initiative is rolled, you can use a Cunning action or your movement as a free action. 

Caution in the Wind

Starting at 17th level, you’ve learnt to throw caution - and your weapons - into the wind. Once on a turn, you can choose to gain sneak attack on an attack that wouldn’t have already. However, if you miss the targets armour class, the damage instead goes to the nearest creature to the target. They may make a Dexterity Saving Throw (DC = 8 + proficiency bonus + intelligence modifier) to take half damage.