Swindler

Cheaters go by many names; swindlers, con-artists, charlatans. Whatever they may call you, whoever you might be perceived as, you’ll always be the first to let the world know that the cards in your hand are there entirely legitimately— you couldn’t have stacked the deck, the dealer shuffled beforehand! You weren’t responsible for the incomprehensibly lucky die rolls, either— you were borrowing the dealer’s dice, after all. Oh, and the drinking game you outlasted the dwarf barbarian in? You couldn’t have watered your drink down, the dealer poured it out for you!

…What? You’re being accused of paying off the dealer? Poppycock.

Swindler’s Luck

At 3rd level, luck seems to appear whenever it benefits you, almost as if you’re cheating. Whenever you make a roll advantage, you may meddle with the roll, forgoing that advantage and roll normally. The next time you roll without advantage, you roll with advantage.

Loaded Dice

At 9th level, you cheat  act with more finesse, giving you more control over your actions. Whenever you make a roll with advantage, you may forgo that advantage to create a loaded die. You may store a number of loaded dice equal to half your proficiency bonus, rounded down. These loaded dice disappear on a short or long rest.

Whenever you roll an attack roll, ability check, or saving throw, you may spend one of your loaded dice to give yourself advantage on that roll. You may only spend one loaded die per turn.

 

Sure Shot

By 13th level, your “luck” is far too consistent to be inconspicuous. When you roll with advantage, you may forgo that advantage to add +3 to the roll’s total. If the roll succeeds, you gain one loaded die.

Don of Con

At 17th level, it’s quite clear you’ve been cheating all this time, some way, somehow. On the bright side, you don’t have to hide it anymore— whenever you miss with an attack roll, you can spend 3 loaded dice to turn that miss into a hit. When you fail a saving throw, you can spend 2 loaded dice to succeed automatically. When you fail an ability check, you can spend 1 loaded die to make the result 20.