Criminal - Charlatan (Grim Hollow)

Charlatans can be seen in most markets
separating fools from their hard-earned coin, and
there is no shortage of fools. Some choose instead
to exploit the upper class, claiming that the
ignorance of spoilt children is far more lucrative,
if a little riskier.

Ranging from the lowliest of hustlers selling
miracle cure-alls to the most audacious con
artists, all charlatans have a knack for fooling
those unfortunate enough to cross their paths.

Rank 1 - Peddler

You are used to lying through your teeth,
telling people whatever they want to hear
in order to separate them from their
money. It keeps you fed and one
step ahead of the law, but you’ll
need a way to run bigger scams if
you want to make real money.

Holdings:

A stash of counterfeit items that you sell and
scam people with.
A secluded stoop that you use as a shelter against
the elements near your place of “business”.

Progression:

You are recruited by a gang of Hustlers, or create
your own group, to participate in more organized
and larger-scale scams.

Rank 2 - Hustler

You have started to work in a group as a face
man, expanding your “clientele” with more
lucrative cons, such as passing off coloured glass
as gemstones, or bleeding wealthy marks dry with
long cons.

Holdings:

A group of miscreants that assist your cons, with
whom you split the spoils of your larceny.

Progression:

You must acquire or create plans for a large-scale
con and procure the necessary elements.

Rank 3 - Con Artist

You have become more daring in your approach,
orchestrating swindles that require planning,
resources, and teamwork in pursuit of a big
payday. You may set your gang about duplicating
famous paintings to be sold in foreign cities, for
example, or forging property title deeds in order
to sell a building you do not own.

Holdings:

A team of charismatic swindlers and skilled
forgers who can recreate items at your request
with great accuracy and detail.
An unmarked warehouse in a disreputable part of
town, where you can store and create forged items
and oversee your operations.

Progression:

Successfully executing a grand con that draws
the outrage of a great noble household, religious
faction, or other powerful institution. It also
makes you famous among other criminals.

Rank 4 - Mastermind

You have become something of a legend within
the underground. Up-and-coming swindlers
approach you to learn at your feet. Whether you
pass on your skills or fleece your new flock is
up to you.

Holdings:

Many detailed plans of cons you have devised
or procured.
A network of talented individuals who work
at your behest, aiding you in orchestrating
your ploys

Applied Leverage 

When you make a Strength
(Athletics) check to force open a door or container,
you may add your profession die to the roll.

Bounty Hunter

Whenever you make a Wisdom (Survival) to track
Criminals, you can add your Profession Die.

Charity Case

When you make a Charisma
(Performance) check to fake an illness, injury, or other
condition, you may add your profession die to the roll.

Contortionist

Whenever you make a Dexterity or Dexterity
(Acrobatics) check to squeeze through a small
space or escape bonds, you can add your
Profession Die to the roll.

Copycat

Whenever you make an Intelligence or
Intelligence (Forgery Kit) check to forge or create
a document, you can add your Profession Die
to the roll.

Disciplinarian

Whenever you make a Charisma (Intimidation)
check while issuing a command to an individual
of lower rank within your background, you can
add your Profession Die to the roll.

Drunkard

Whenever you make a Constitution check to
determine if you will throw up, pass out, or how
severe a hangover is, you can add your Profession
Die to the roll.

Elusive

Whenever you make a Dexterity (Stealth) check
to hide or blend into a crowd of humanoids
that share your background, you can add your
Profession Die to the roll.

Gambler

Whenever you make a Dexterity (Sleight of Hand)
or Wisdom (Perception) check to cheat at a game
or catch someone else cheating, you can add your
Profession Die to the roll.

Grifter

Whenever you make a Charisma (Deception)
check, and are attempting to pass off a fake object
as authentic, you can add your Profession Die
to the roll.

Heister

Whenever you make a Wisdom (Perception)
check to spot traps, sentries, and other security
measures, you can add your Profession Die
to the roll.

Impressionist

Whenever you make a Charisma (Performance)
or Charisma (Deception) check to mimic the
mannerisms, voice, or appearance of another
humanoid, you can add your Profession Die
to the roll.

Interrogator

Whenever you make a Charisma (Intimidation)
check to extract information from an enemy who
is restrained, you can add your Profession Die
to the roll.

Looter

When you make an Intelligence (Investigation)
roll to find hidden valuables, you may add your
profession die to the roll.

Menacing Presence

Whenever you make a Charisma (Intimidation)
check, and are interacting with Academics,
Common Folk, or Seafarers, you can add your
Profession Die to the roll.

Nimble Fingers

Whenever you make a Dexterity (Thieves’ Tools)
check to pick a lock, you can add your Profession
Die to the roll.

Quick Fingers

Whenever you make a Dexterity (Sleight of Hand)
check to place a small object on a humanoid or
sneak something into their food or beverage, you
can add your Profession Die to the roll.

Renowned

Whenever you make a Charisma (Persuasion)
check, and are interacting with Military,
Outlanders, or Criminals, you may add your
Profession Die.

Ropesman

Whenever you make a Strength (Athletics) or
Dexterity (Acrobatics) check to climb, move
along, or jump onto ropes, you can add your
Profession Die.

Sentry

Whenever you make a Wisdom (Perception) check
while on watch duty or defending a fortification,
you can add your Profession Die to the roll.

Sticky Fingers

When you make a Dexterity (Sleight
of Hand) check to snatch something quickly, you may
add your profession die to the roll.

Urban Sprinter

Whenever you make a Strength (Athletics) or
Dexterity (Acrobatics) check while running away
from a pursuer, or pursuing someone else, you
can add your Profession Die to the roll.

Vacant Expression 

When you make a Charisma
(Deception) check to feign ignorance and you are
interacting with an Academic, Aristocrat, Clergy, or
Militarist, you may add your profession die to the roll.