Roguish Archetype
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Outlaw
In the untamed wilderness, you can have anything you can get your hands on, as long as you have the guts to take it for yourself. This belief is cherished by the archetypical bandit, who is ruthless and self-seeking, but not foolish; bandits nearly always run in gangs to protect themselves from other bandits and from the law. As threatening as a bandit might be when backed into a corner, a gang working in unison is a force to be feared. Such a team can rob anything from a bank to a moving train — no lawman could hope to stop them.
Stick Up
Starting at 3rd level, you can use your Sneak Attack against a target within 30 feet that does not have any allies within 5 feet of it. You can make a Sneak Attack in this way even if you don’t have advantage on the attack roll, but not if you have disadvantage on it.
Additionally, when you hit a creature within 5 feet with a Sneak Attack, you can use your bonus action to steal one object it is carrying, but is not holding in a hand. For example, you could steal a drawstring pouch the target is wearing or a dagger that is sheathed at its side. You must have a free hand to steal an object in this way.
Mob Action
Beginning at 9th level, you can always gang up on unsuspecting foes. You can grant your Cunning Action to an ally within 5 feet of you as a bonus action. Your ally can use its reaction to take the Dash, Disengage, or Hide action.
Jailbreak
By 13th level, no prison can hold you. You have advantage on ability checks you make to slip bonds, escape grapple, or pick locks. Moreover, you are able to undetectably conceal a small tool of your choice, such as a file or a small knife, on your person at all times. Lastly, you are immune to the imprisonment spell.
Most Wanted
Starting at 17th level, your name is feared throughout the land, with ludicrously high bounties promised for your gang. Once on each of your turns, in combat, if your allies outnumber the allies of a creature you hit with an attack, you can add 2d6 to the damage roll.
