Assassin (5A)

This is a Rogue subclass for 5A.

You focus your training on the grim art of death. Those who adhere to this archetype are diverse: hired killers, spies, bounty hunters, and even specially anointed priests trained to exterminate the enemies of their deity. Stealth, poison, and disguise help you eliminate your foes with deadly efficiency.

Greyhawk There is an assassins' guild in Greyhawk City, often in conflict with the thieves' guild. The most famous assassins of the Flanaess were in the Scarlet Brotherhood, but little is known of what happened to them. A few former scarlet assassins are rumored to have started their own assassins' guilds in other cities.

Source: Player's Handbook

Subclass Features

Bonus Proficiencies

When you choose this archetype at 3rd level, you gain proficiency with the disguise kit and the poisoner's kit. If you are already proficient in one of these, you learn a language, vehicle, or tool proficiency for each kit you were already proficient with.

Assassinate

Starting at 3rd level, you are at your deadliest when you get the drop on your enemies. You have advantage on attack rolls against any creature that hasn't taken a turn in the combat yet. In addition, any hit you score against a creature that is surprised is a critical hit. Note: A creature stops being surprised when its initiative comes up, even when it is not allowed to act.

Infiltration Expertise

Starting at 3th level, you can unfailingly create false identities for yourself. You must spend seven days and 25 gp to establish the history, profession, and affiliations for an identity. You can't establish an identity that belongs to someone else. For example, you might acquire appropriate clothing, letters of introduction, and official- looking certification to establish yourself as a member of a trading house from a remote city so you can insinuate yourself into the company of other wealthy merchants.

Thereafter, if you adopt the new identity as a disguise, other creatures believe you to be that person until given an obvious reason not to. If a wary creature suspects something is amiss, you have advantage on any Charisma (Deception) check you make to avoid detection.

This is most often used as a part of an adventure hook, or as preparation for a mission, outside the time-frame of the mission itself. You can also establish a number of generic , reusable cover identities you can adopt as needed.

Poisoner

At 9th level, you have learned how to create and use poisons. Whenever you finish a long or short rest, you can use a poisoner's kit to create 1d3+1 doses of a deadly poison. The creation may be an ingested or injury poison (your choice) and lasts until used or you take a long rest.

Assassin's Death (Ingested or Injury): A creature subjected to this poison must make a Constitution saving throw DC = 8 + your proficiency bonus with the poisoner's kit. On a failed save the creature takes 1d12 damage for every 5 levels you have in this class (round fractions down) and gains the poisoned condition for one minute. If the poison is ingested, the creature is also incapacitated while poisoned this way. If the saving throw is successful, the creature takes half damage and suffers no additional effects.

Impostor

At 13th level, you gain the ability to unerringly mimic another person's speech, writing, and behavior. You must spend at least three hours studying these three components of the person's behavior, listening to speech, examining handwriting, and observing mannerisms.

Your ruse is indiscernible to the casual observer. If a wary creature suspects something is amiss, you have advantage on any Charisma (Deception) check you make to avoid detection.

Death Strike

Starting at 17th level, you become a master of instant death. When you attack and hit a creature that is surprised, it must make a Constitution saving throw (DC 8 + your Dexterity modifier + your proficiency bonus). On a failed save, double the damage of your attack against the creature.

Editor's Notes

Infiltration Expertise moved to level 3. That opened a slot at level nine, where I put a poisoner ability Treeantmonk introduced for his version of this subclass.