Spy (5e Background)

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At some point or another you secretly gathered information on a group of people or maybe one person. Maybe you were hired by a rival or political enemy, maybe you were searching for military information to help the opposing army, maybe you were trying to fulfil your own agenda, but regardless you are good at finding things and hiding your true self. You are used to living on the edge of danger, and doubly used to doubting people's intentions. Who did you spy for, yourself or some benefactor? Who or what did you spy on? What secrets did you uncover? Why did you stop? Or did you?

Skill Proficiencies: Two from Deception, Insight, and Stealth

Language Proficiencies: Two of your choice

Tool Proficiencies: Disguise kit, Forgery Kit

Equipment: A disguise kit, a forgery kit, a small mirror, a small crumpled note with secrets you stole (could be battle plans, blackmail material, or coordinates to an unknown place), a set of common clothes, and a small pouch with 15gp.


What were you looking for when you were spying?

d6 Specialization
1 Coordinates to a hidden artifact.
2 Evidence of intrigue.
3 Battle plans.
4 Location of a particular person.
5 Blackmail material.
6 Trade secrets.

Feature: Master of Many Faces[edit]

You have honed your ability to shape your personality and to read the personalities of others. You gain the following benefits:

You have an advantage on Charisma (Deception) and Charisma (Performance) checks when trying to pass yourself off as a different person.

If you spend time observing a creature, you can then take a short or long rest to craft a disguise you can quickly don to mimic that creature. Making the disguise requires a disguise kit. You must make checks as normal to disguise yourself, but you can assume the disguise as an action.

Suggested Characteristics[edit]

d8 Personality Trait
1 I always have an aloof smile plastered on my face, no matter the situation.
2 I am uncomfortable in open spaces, where I'm too exposed.
3 I change my attitude and personality to blend in with the people around me.
4 I always check the escape routes of every building I enter.
5 I have trouble trusting people, especially those closest to me.
6 I have a habit of listening in on the conversations of others.
7 I prefer not to talk unless it's necessary.
8 I write anything I think is important in code.
d6 Ideal
1 Exposure: The evils of the world must be exposed. (Good)
2 Blackmail: Ooh, isn't this a dirty secret...? Shame if it fell into the wrong hands: mine. (Evil)
3 Contract: The information is bound to the person who hires me, no one else may see it. (Lawful)
4 The Game: If this came out to the public... That noble would be done for... That one too... Oh what fun! (Chaotic)
5 Self: The information is good, coming out alive better, the coin I'll get from this, totally worth it. (Neutral)
6 Knowledge: He knows something, and I need to know it too. (Any)
d6 Bond
1 I fell in love with someone I was spying on.
2 I had some colleagues in a spy ring I used to be a part of that I trade information with from time to time.
3 I have secrets that I've uncovered that should never see the light of day.
4 One of my friends was hanged for treason. My helplessness to aid him still haunts me today.
5 A good person was ruined with information I gathered on him. I am trying to atone.
6 A servant in a castle saw me spying on her lord. I fled and hope I will never have to see her face again.
d6 Flaw
1 I have no problem with betraying people who trust me.
2 Some people want to kill me, to make sure I never tell a secret they'd rather have untold.
3 I've worn so many disguises, I've lost sight of who I truly am.
4 I never share secrets with anyone.
5 I don't save people who can't save themselves. The Game is harsh and the stupid and flamboyant tend to die the first.
6 I never forget an insult, and I bide my time for revenge.

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