Highwayman

Strength-based rogue subclass focused on the use of versatile weapons and intimidation to stab, slash and crush your enemies and steal their treasure. A good bandit also needs to be able to escape if the shakedown goes bad.

Rough Exterior

When you choose this archetype at 3rd level you gain expertise in the intimidation skill.

Brute Force

Your style of combat is more focused on strength and intimidation than sly cunning. You gain proficiency with all versatile weapons and can sneak attack with them even if they do not have the finesse tag.

Shake Down

At 3rd level, your life of extorting others for their possessions has come to help you in combat. As a bonus action, you may make a charisma (intimidation) or a strength (intimidation) check against a creature’s wisdom (insight). If you succeed, you have advantage on all attacks against the creature until the start of their next turn.

Hand it Over

At 9th level, you have had more experience taking things from others by force. When openly taking something from someone or opening a lock, you may use your strength modifier instead of your dexterity modifier for sleight of hand and thieves’ tools checks. Sleight of hand checks made against creatures under the effect of your Shake Down ability are made at advantage.

Get Away

At 13th level, you have a knack for getting away just in time. Creatures affected by the shakedown ability can not take opportunity attacks against you or any of your allies. You also gain proficiency in land vehicles.

No Survivors

At 17th level, you’ve mastered the ability to make sure there is no one left to tell of your exploits. You may add your sneak attack damage to attacks of opportunity made with weapons that you can sneak attack with.