Believe it or not, even the Gods of Luck and Fortune have chosen ones that they imbue with certain powers. Of course, being a god of luck doesn’t mean just handing it over to the chosen one willy nilly. No, the chosen one must prove that they are worthy of such a mantle by demonstrating their natural affinity to bending the curve of probability. These roguish archetypes are known as gamblers, and they live life on the edge. Betting on (and against!) allies, foes, and events all around them.

Place Your Bets

When you select this roguish archetype at 3rd level, before you or any of your allies make an attack roll, you can use your reaction to place a bet. You must tell the DM before the roll is made whether or not the roll will succeed or fail. After the attack roll is made, if your guess was correct you are rewarded a gambler’s die. If your guess was incorrect nothing happens. You can only have one gambler’s die at a time.

If you have the gambler’s die, you can expend it when you make an attack roll. Spending your gambler’s die gives you advantage on that roll.

Easy Money

At 3rd level, you are excellent at making money while traveling. As long as you are in a somewhat civilized area that’s predominantly populated by humanoids with an average Intelligence scores of 8 or greater, you are carrying at least 10 gp, and have a gambler’s die available, you can gamble to earn extra income. To do so, you must spend eight hours of downtime gambling, at the end of which you expend your gambler’s die. You earn 10 gp from your efforts. This amount increases to 100gp at 5th level, then 1,000 gp at 11th level.

Once you use this feature, you can’t use it again until you complete a long rest.

Additionally, you gain proficiency with the dice set.

Call Your Bluff

Starting at 9th level, you have an incredible sense for when people are lying to you. You have advantage on all Wisdom (Insight) checks to detect lies.

In addition, you can expend your gambler’s die when you wish to detect a lie. If you do, you automatically know what you’re hearing is a lie or not.

One-in-a-Million Chance

At 13th level, you possess supernatural luck. After you make an attack roll, ability check, or saving throw, you can expend your gambler’s die to do one of the following:

• Reroll the die. You must use the new roll.
• Add +5 to the die roll.

You must choose to use your gambler’s die in this way after you make the roll, but before the DM tells you whether or not you succeeded.

Full House

At 17th level, your natural luck assists you in combat. Whenever you hit a creature with your Sneak Attack, you can expend your gambler’s die to increase your Sneak Attack damage for that attack against that creature by 5d6.