Criminal - Cutthroat (Grim Hollow)

Some crooks lie to get what they want. Some
steal it when its owner isn’t looking. Then there
are those who walk up to a target and explain
the deal: give me what I want or bad things will
happen to you. Call it “protection” or call it
extortion, it is perhaps the most straightforward
form of crime, favoured by the violent and the
ruthless.

Most Cutthroats start out working in a preestablished
gang, collecting fees and extracting
payments on behalf of a boss. A small gang might
be responsible for shaking down a handful of
businesses, while the most powerful of crime
lords may influence prominent cities or regions.

Rank 1 - Tough

Working the impoverished regions of town,
you’re a criminal who will mug those who walk
down the wrong alley at night, or extort unwary
travelers for safe passage along a road.

Holdings:

A hideout where you can seek shelter from the
elements, and from local law enforcement.

Progression:

Acquire a building to use as a centre of operations
for your illicit activities, and a handful of other
criminals willing to follow your lead.

Rank 2 - Crew Leader

Being the leader of your ragtag team comes with
some nice perks. Shop owners shower you with
gifts and praise in order to remain on your good
side during your weekly rounds. Some will even
go out of their way to source rare and valuable
items that you require, if they believe doing so
will earn your favor.

Holdings:

A group of thugs that you command, overseeing
their various ploys.
Knowledge of back alleys and slipways that allow
you and your group to escape unpursued by local
law enforcement.
A rundown establishment that you and your
fellow henchmen operate out of.

Progression:

Your group of thugs has progressed in size to
exert control over an entire village or district
within a city.
A sizable collection of shop owners that you can
regularly exploit for “protection”.

Rank 3 - Gang Boss

You are now a big fish in a small pond, often
butting heads with rival gangs. Your presence is
not quite strong enough to force your competition
out of your territory. Whether you make a bid for
control or they do, one thing is for certain: there
will be blood in the streets.

Holdings:

Multiple warehouses and business fronts to
launder and store your spoils until a suitable
buyer can be located.
A network of contacts that you use to acquire and
sell illicit goods.

Progression:

You must overthrow a rival crime lord, or claim
the territory of all surrounding rival gangs.

Rank 4 - Crime Lord

You sit at the top of the criminal pyramid of your
city or region. While there are still gangs that you
don’t directly control, they know to stay well clear
of your territory.

Holdings:

An expansive territory that you control,
overseeing the criminal businesses within the city
and taking a cut of their profits in exchange for
protection.A number of personal secrets and incriminating
evidence about high-ranking nobles, clergy, or
business magnates.
A corrupt, influential state official who does
your bidding and provides you with confidential
information.

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.