Rogue: Enforcer

Original Source: Original Homebrew

Most rogues are quiet, subtle, and deft lightfoots that slink in shadows, preferring to keep the attention off of themselves. These individuals protect themselves and dispatch their marks with light weapons, if not ranged ones that allow them to remain far away and unseen. The enforcer, then, is the opposite - a crafty individual who, while more than capable of subtlety when it suits them, thrives best when drawing the attention of the enemy on themselves. Derided as thugs or brutes by their victims, these rogues are suited to be the right hands of those of more subtle or kind approaches, striking fear into those that cross them and using all manner of dangerous weapons to inflict pain on any who cross their path.

Bonus Proficiencies

When you become an enforcer at 3rd level, you gain proficiency with medium armor and martial weapons.

Cunning Action: Hired Muscle

Starting at 3rd level, you can use a bonus action to make a Strength (Athletics) check to shove a creature, or to try to intimidate a creature with a fearsome display. A creature you try to intimidate must make a Wisdom saving throw against your passive Intimidation or be Frightened of you until the end of your next turn.

Brutal Attack

Starting at 3rd level, your expertise at inflicting pain allows you to bring the pain with weapons of any size. Your sneak attacks can be used with any weapons, but if they are not finesse or ranged weapons, the extra dice from sneak attack is halved (rounded down) unless that creature is frightened of you.

You also gain an additional way to use your Sneak Attack; you don't need advantage on the attack roll to use your Sneak Attack against a creature that is frightened of you as long as you don't have disadvantage on the attack roll. All the other rules for Sneak Attack still apply to you.

Street Smarts

At 9th level, your uncanny ability to talk the talk and walk the walk manifests in the following ways:

Know Fear

At 13th level, your knowledge of fear makes you harder than most. You have advantage on saving throws against being frightened. Additionally, if you if you spend at least 1 minute observing or interacting with another creature outside combat, you can size them up and learn how susceptible they are to mental pressure. You immediately learn if the creature is immune to the frightened condition. If they aren't, you learn if they have advantage on saving throws against the frightened condition, as well as its bonus on Wisdom saving throws.

Exploit Weakness

At 17th level, you have advantage on attack rolls against creatures that are frightened, or who are below half of their maximum hit points. Additionally, your weapon attacks score a critical hit on a roll of 18-20 as long as you have advantage on the attack roll.