Roguish Archetype: Gambler

You have spent your life in the seedy taverns and back alleys of the world perfecting your craft. While others believe that chance favours nobody, gamblers know that even luck can be influenced if you know how. With only the simplest of deceptions, you have learned to bluff your way to victory in anything you attempt.

Ante Up

When you choose this archetype at 3rd level, you gain access to a number of Wagers which increases as you level up and are replenished on a long rest. As a bonus action on your turn, you may choose to use one of these Wagers. You may roll 1d4 and the result is your Ante Bonus. You then gain any effects equal to or lower than your Ante Bonus in the Ante Bonus table for the next minute. All effects on the Ante Bonus table are stacking unless otherwise stated.

Rogue Level	Wagers
3rd	5
6th	7
9th	9
12th	11
15th	13
18th	15

Raise the Stakes

You are always looking for ways to improve your odds. Starting at 3rd level, you may expend one of your Wagers as a bonus action on your turn in an attempt to increase your current Ante Bonus. Roll 1d6 and, if the result is greater than or equal to your current Ante Bonus, you may replace it with this number. If successful, you may then repeat this on your subsequent turns, increasing the roll to 1d8, 1d10, and finally 1d12.

If your new roll is lower than your current Ante Bonus, your Ante Bonus is removed and you have a -2 penalty to all Attack Rolls and Saving Throws until the end of your next turn.

Credit: Ian Llanas

Credit: Labyrinth

Ante Bonus Table

Ante Bonus	Effect
1	+2 to Charisma skill checks
3	+1 to Attack Rolls
5	Sneak Attack dice change to d8s
7	+2 to all Saving Throws
9	+2 to Attack Rolls
11	All successful attack rolls count as Critical hits

Hustle

From 7th level, you may turn your favour into misfortune for another. As an action on your turn, you may remove your Ante Bonus to give a target you can see a penalty. You must make a Charisma (Deception) check contested by the target’s Wisdom (Insight). If you win the contest, the target receives -2 to all Attack Rolls and Saving Throws for the next minute. If you fail the contest, this ability does nothing and you still lose your Ante Bonus.

Cash Out

You know when it's time to call and time to fold. From 13th level, you may remove your Ante Bonus from yourself as a bonus action to instantly give yourself temporary hit points equal to your Ante Bonus multiplied by 2.

Alternatively, you may attempt to remove your penalty from a target to deal damage. The target must succeed a DC15 Wisdom saving throw or takes psychic damage equal to your Rogue level multiplied by 3.

All-In

At 17th level, the dice always seem to be loaded in your favour. You may roll your die twice when attempting to Raise the Stakes. Additionally, you also keep your Ante Bonus when successfully using the Hustle feature.