Oppressor (Rogue)

The term assassin conjures an image of a black-hooded rogue slinking through the darkness, poised to put a dagger through the throat of his victim. These silent killers are hired when a murder must be committed without drawing undue attention, or when the one commissioning the deed would like to remain nameless.

Sometimes, however, a killing is meant to send a message to the living. Crimelords often make examples of lackeys who have failed in their tasks, and rulers frequently find it useful to display their intolerance for rabble-rousers and insurrectionists with special shows of force. Even churches sometimes use less-than-subtle methods to prove themselves worthy of their followers' faith and coin. Missions that involve making an example of the victim call for the special talents of an oppressor.

Oppressors specialize in brute-force assassinations, although many of their assignments are less deadly "legbreaking" missions. Members of this archetype know how to bloody their targets before killing them and how to intimidate bystanders into staying out of the fray. The brutal and violent methods of an oppressor invariably make a lasting impression on the minds of witnesses, who thereafter tend to consider opposing the oppressor's employer an unhealthy prospect.

The typical oppressor is a fulltime employee of a crime boss, thieves' guild, or local ruler. Independent agents are rare in this profession, primarily because the populartions that oppressors terrorize would certainly retaliate were the assassins not under the constant protection of their employers. A few oppressors are paid to root out their employers' enemies wherever they lurk or to serve as a symbol of their employers' power. Such agents generally find that traveling with others helps deter the wrath of those they terrorize.

Oppressors are almost universally scorned by the societies in which they work, but most of them never give this social ostracism a second thought. They love their work and get paid well for it, and that is enough for them. Oppressors do not expect the affection of others, nor do they seek it. Theirs is a lonely profession, but those who choose it know the consequences well in advance.

Keep Awake

Starting at 3rd level, whenever you would deal enough damage to reduce an opponent to 0 hit points, you may instead reduce them to 1 hit point and stun them. They are considered stunned until the end of your next turn. This ability does not affect undead or constructs.

Brutal Grappler

Starting at 3rd level, whenever you successfully land a melee weapon attack, and apply sneak attack damage, you may attempt to grapple the target as a bonus action. Additionally, you may apply your sneak attack damage to your unarmed strikes, even if you use your Strength to calculate your attack and damage rolls, so long as you are grappling your target.

Infamy

By 9th level, the oppressor can easily take advantage of their reputation. You now have advantage on Charisma (Intimidation) checks, but disadvantage on Charisma (Persuasion) checks, made in areas you are known as an Oppressor, if you are not attempting to disguise yourself.

Fighting Style

At 9th level, the oppressor may take a Fighting Style from the Fighter class list.

Intimidating Edict

Starting at 13th level, if the oppressor uses their Keep Awake ability on an opponent in full view of other creatures, they can cast Mass Suggestion on the crowd, as a 6th level spell. Targets have disadvantage on the save if the victim is a leader or someone respected by those being intimidated. The oppressor may only use this ability once per long rest.

Intimidating Presence

Beginning at 17th level, any creature with an Intelligence of 3 or higher that attempts to harm the oppressor must make a Wisdom saving throw (DC = 8 + oppressor's Proficiency bonus + oppressor's Charisma modifier) or have disadvantage on all attack rolls, saving throws, and ability checks until the start of their next turn. Success means that they are immune to the Intimidating Presence until the end of their next long rest. If a target is immune to being Frightened, they are immune to this effect.

Credits

Flavor text and Concept: Dragon Magazine #312: "ASSASSIN: Specialty Prestige Classes" by Wil Upchurch

Artwork: Used without permission, from http://forums.wesnoth.org/viewtopic.php?t=24303&f=9

Conversion: whitemagetam