Scoundrel (TS)

Stack the Odds and Escape the Consequences

Swindling, sweet talking and sneaky, you convice your marks that you are, in fact, extraordinarily lucky. Of course, the less they know about your loaded dice and the ace up your sleeve, the better.

Scoundrels are Rogues known by the public for their con-artistry and by the authorities for their elusiveness. Despite their percieved self-interest, they work best as part of a team. With partners at their side, they seamlessly plan and improvise schemes, splitting their winnings and encouraging tight teamwork.

By Touched_spaghetti

Original Page: Rogue Subclass: Scoundrel (5.24)

Level 3: High Roller

You have cultivated skills that allow you to win games of chance and skill - both legitimately and by cheating. You have proficiency in two kinds of Gaming Sets of your choice, and you have Expertise when making checks with Gaming Sets with which you are proficient.

In addition, whenever you fail a Charisma (Deception) or Dexterity (Sleight of Hand) check, you can re-roll the check, and must use the new roll. You can re-roll a check in this way a number of times equal to your Dexterity modifier (minimum once) and you regain all expended uses when you finish a Long Rest.

Run!

Sometimes, when your cheating gets found out, talking your way out of the situation isn’t an option, and the only appropriate way to save your skin is to escape. You gain the following benefits:

Quick Dash:

When you use your Cunning Action feature to Dash or Disengage, you can move an extra 10 feet before the end of your turn.

Crowd Cover:

You can attempt to Hide behind creatures that are your size or larger, and have Advantage on the Dexterity (Stealth) check if you do so amongst a crowd of two or more creatures that are your size or larger and are within 5 feet of each other.

Disorient Pursuer:

When you deal Sneak Attack damage to a creature, its Speed is reduced by 10 feet until the start of your next turn.

Partner in Crime

When you finish a Short or Long Rest, you can designate one willing creature within 30 feet to be your ‘Partner in Crime’, a confidant that aids you in your exploits, and whom you aid in return. This creature continues to be your Partner in Crime until you designate a different creature, until another Rogue makes it their Partner in Crime or until you die.

While you and your Partner in Crime are within 30 feet of each other, you both gain the following benefits:

Silent Speech:

You can communicate with Partner in Crime silently so long as you can see one another, using subtle gestures to convey your meaning.

Mutually Helpful:

You can take the Help action as a Bonus Action, but only to aid your Partner in Crime.

Watch their Back:

When your Partner in Crime fails a saving throw, you can use your Reaction to allow them to re-roll the saving throw, taking the new result. You can each use this Reaction once, and regain its use after finishing a Short or Long Rest.

Exceedingly Slippery

You have become extraordinarily difficult to pin down. The Restrained condition no longer imparts Disadvantage on your weapon attacks. In addition, when you use the Withdraw option of your Cunning Strikes feature, you can automatically end all instances of the Grappled and Restrained conditions on yourself.

Tag-team Attack

When you take the Help action to give your Partner in Crime Advantage on an attack roll, or vice versa, if the attack hits, the target takes an additional 3d6 damage of the attack’s type, and the target has Disadvantage on attacks against both of you until the start of your next turn.