Mask Initiate Image

You are an experienced criminal associated with the largest guild of organized crime present throughout the world. You have spent a lot of time amongst members of the the Mask,  a criminal syndicate dedicated to the worship of The Masked God. Only fully fledged members of The Mask gain the full benefits and responsibility, and the challenge to become a member is extremely difficult and often deadly. If you wish to be a former member (or perhaps still a member) of the Mask, talk to the DM about the challenge of becoming one and your history with the guild.

 
Skill Proficiencies: Choose two from among Deception, Stealth, or Religion
Tool Proficiencies: Choose one from among Disguise Kit, Forgery Kit, Poisoner's Kit, Thieves' Tools
Equipment: A holy symbol of The Masked God, a set of dark common clothes including a hood, and a pouch containing 15 gp
 
Criminal Specialty

The Mask is home to all kinds of outcasts from society that choose to follow The Masked God. The breadth of jobs The Mask accepts allows members who have almost any kind of disorderly specialty. Choose the role you played in your career with The Mask, or roll on the table below.

d8 Criminal Specialty
1 Blackmailer
2 Burglar
3 Enforcer
4 Fence
5 Priest
6 Hired killer
7 Pickpocket
8 Smuggler
 
Feature: Network of the Mask

You have a reliable and trustworthy contact within The Mask who acts as your liaison to the entire guild. You know how to get messages to and from your contact, even over great distances; specifically, you know the messengers, caravan masters, and sailors associated with The Mask who can deliver messages for you.

 
Suggested Characteristics

Members of The Mask might seem like villains on the surface, and many of them are villainous to the core. There might be honor among thieves, but criminals rarely show any respect for the law. However, the authority within the guild are almost always obeyed without question due to the divine providence given to the leaders of The Mask.

d8 Personality Trait
1 I always have a plan for what to do when things go wrong.
2 I am always calm, no matter what the situation. I never raise my voice or let my emotions control me.
3 The first thing I do in a new place is note the locations of everything valuable—or where such things could be hidden.
4 I would rather make a new friend than a new enemy.
5 I am incredibly slow to trust. Those who seem the fairest often have the most to hide.
6 I don’t pay attention to the risks in a situation. Never tell me the odds.
7 The best way to get me to do something is to tell me I can’t do it.
8 I quote (or misquote) sacred texts and proverbs in almost every situation.
d6 Ideal
1 Honor. I don’t steal from others in the trade. (Lawful)
2 Freedom. Chains are meant to be broken, as are those who would forge them. (Chaotic)
3 Charity. I steal from the wealthy so that I can help people in need. (Good)
4 Greed. I will do whatever it takes to become wealthy. (Evil)
5 People. I’m loyal to my friends, not to any ideals, and everyone else can take a trip down to Avernus for all I care. (Neutral)
6 Redemption. There’s a spark of good in everyone. (Good)
d6 Bond
1 I’m trying to pay off an old debt I owe to a generous benefactor.
2 My ill-gotten gains go to support my family.
3 Something important was taken from me, and I aim to steal it back.
4 I will become the greatest thief that ever lived.
5 I’m guilty of a terrible crime. I hope I can redeem myself for it.
6 Someone I loved died because of a mistake I made. That will never happen again.
d6 Flaw
1 When I see something valuable, I can’t think about anything but how to steal it.
2 When faced with a choice between money and my friends, I usually choose the money.
3 If there’s a plan, I’ll forget it. If I don’t forget it, I’ll ignore it.
4 I have a “tell” that reveals when I’m lying.
5 I turn tail and run when things look bad.
6 An innocent person is in prison for a crime that I committed. I’m okay with that.
 
Variant Mask Initiate: Chaplain

Although your capabilities are not much different from those of a burglar or smuggler in The Mask, you have focused on the worship of the faceless god more than ordinary criminal activities. You gain the Acolyte's "Shelter of the Faithful" feature

 
Variant Feature: Shadow Economy

You are always able to find a job contracted with The Mask. In any civilization where The Mask has a presence, you know where to find employment with the guild. These jobs can be anything from petty theft to destroying an infestation of unsavory creatures. 

 
Mask Initiate Image

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