Gambler

"Nothing to lose." That was the motto that he had lived his entire life by, from his early days as an orphan in Greystone, to this moment, when he was running for his life from an unexpected troll that inhabited the ruins he was exploring.

She eyed her opponent across the table. As their eyes met, the corner of his mouth gave the smallest of twitches. He was bluffing - she was sure of it. She reached forward and pushed in another stack of shiny gold coins.

"Well, that concludes negotiations!" shouted the leather-clad half-elf as he drew his rapier from his belt. A goblin came flying at him, but tripped over a root at the last second, making it an easy kill. The half-elf had always been lucky like that - now he was just hoping his fortunes wouldn't turn at an inopportune moment.

Some play to win, others for fortune or fame. Some even play for love, of all the most dangerous game. Regardless, the only way to get out before the house gets its inevitable way is to fold while you are ahead.

The gambler is always pushing their luck, whether it be in games of chance or deadly combat. Somehow, they seem to come out ahead more times than not. Some gamblers are self-asserting and boastful, others are timid and superstitious.

Roll the Dice

3rd-level Gambler feature

You seem to get lucky at the best moments, allowing you to survive the most unlikely situations.

As a bonus action, roll four d4s. You gain a benefit depending on which number came up most often on the dice. If multiple numbers came up equally often, you gain all those benefits. These benefits last for 1 minute, or until you use this feature again. You can use this feature a number of times equal to your proficiency bonus, and you regain all uses when you finish a long rest.

d4	Benefit
1	Quick on your Feet: Your movement speed increases by 10 feet, and your movement does not provoke opportunity attacks
2	Skin in the Game: You are considered to have half cover, and you gain Temporary Hit Points equal to twice your level in this class
3	Eye for Weakness: Your Sneak Attack damage dice now explode (as long as you roll the maximum number on any die, you can reroll it and add it to the total), and your attacks crit on a 19
4	Spray and Pray: If you take the Attack action on your turn, you can use your Cunning Action to make a single weapon attack

High Roller

3rd-level Gambler feature

You gain expertise in one gaming set of your choice, and you have advantage on other ability checks that use this gaming set, such as a Sleight of Hand check to cheat by switching a card, or an Insight check to try to tell if your opponent is bluffing.

Additionally, you have advantage on Death Saving Throws.

Evens and Odds

9th-level Gambler feature

The dice just seems to go your way more often than not. When you use Roll the Dice, you can choose one of the dice and reroll it before determining the outcome. You must use the new result.

Pawn Gambit

13th-level Gambler feature

Enemies just seem to miss you when it matters most. When you are the target of an attack, you can use your reaction to redirect it to a different creature that is within 5 feet of you and also in range of the attack. Once you do this, you cannot do so again until you finish a short or long rest.

Diamond Hands

17th-level Gambler feature

If you only get a single benefit from Roll the Dice, you can choose one of the other benefits and gain that one as well.

If you gain two benefits, you have advantage on all attacks you make on that turn.

If you gain all four benefits, you can take an extra Action on that turn, during which you can trigger Sneak Attack an extra time.