Gambler

As a gambler, you exceed in buffing your damage and turn getting lucky into a habit rather than a trick. Designed for high damage if you play your cards right and the ability to strengthen the one roll type that no one else has any strength in being luck. If anyone can make anything happen, its the gambler, as long as he still has a trick or two up his sleeve. Intended mainly to take the rogue DPS to a whole other level, can also provide strong utility with many luck based abilities.

Gambler's Longshot

When you roll to attack, on a successful hit and after rolling damage, you may roll an extra D20 as a luck check that will multiply the damage dealt by a multiplier. The multipliers are as follows. On a 1-4 you deal no damage whatsoever for that attack, on a 5-8 you deal half damage rounded up, on a 9-11 you deal normal damage, on a 12-15 you deal 1.5 times damage rounded up, on a 16-19 you deal double damage, and on a natural 20 you deal triple damage. This ability cannot be used in conjunction with bardic inspiration as your luck is yours alone or with a natural 20 on an attack roll because luck is already on your side. At level 3 you start out with 3 Longshot Die and gain an additional one at level 5, 10, 15, and 20 for a total of 7 at max level. All die can be regained after a long rest and half the amount used can be regained on a short rest rounding up.

Ace Up the Sleave

Anytime you roll a natural 20, you may choose to save that natural 20 as an Ace for later use for any other roll including saving throws, attack rolls, skill checks, and Gambler's Longshot. If you choose to save the 20 as an Ace, you must re roll the die, and mark down that you saved that Ace. You may not give the Ace to any of your party members. All Ace's go away after a long rest. At level 15 you gain an additional Ace slot for a possible total of 2 Aces for two sleeves.

Professional Gambler

You may add your charisma modifier to all Luck checks to include Gambler's Longshot as well as any re roll using the Luck feature or Ace Up the Sleeve as an additional modifier.

Royal Flush

For one minute you gain advantage on every roll to include: saving throws, ability checks, attack rolls, Gambler's Longshot rolls, and death saving throws if you happen to be knocked out during the duration. If you would have disadvantage on a roll, you instead gain advantage despite the supposed difficulty of the disadvantaged roll. If you already have advantage, you may instead roll a D20 three times and take the highest of the three rolls. After the minute is up, you have spent all of you luck and must roll disadvantage on all rolls until your next short rest. This ability recharges after a long rest.