Criminal

Criminals serve and thrive off the seedy underbelly of society. While many people run afoul of the law, this background is for people who make their livelihoods entirely outside the law. Rarely respected or honoured within society, Criminals often hide their true profession from others.
Skill Proficiencies: Choose one from Acrobatics, Athletics, Deception, Intimidation, Sleight of Hand, Stealth.
Languages: Thieves' Cant.
Tool Proficiencies: Thieves' Tools.
Equipment: Thieves' tools, fake currency in a drawstring pouch to deter pickpockets, a set of dark common clothes including a hood, and 15gp.

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Charlatan

Charlatans can be seen 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.
Skill Proficiency: Deception
Additional Equipment: a lockbox with a secret compartment, a forged Merchant's Guild membership certificate, imitation fine clothes.

False Identity

Upon spending an hour writing and talking to the right people, and succeeding on a DC15 Charisma (Deception) check, you can create yourself a new identity with fake identification.

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 organised 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 foragers 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.

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Cutthroat

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 pre-established 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.
Skill Proficiency: Intimidation.
Additional Equipment: A kidskin bag of loaded dice, a snuff box, a pocket watch that runs five minutes fast.

Underground Connections

Upon spending an hour asking around, and succeeding on DC15 Charisma (Intimidation) check, you can prove your credibility and find a contact in a local gang, Thieves' Guild, or underground network. This contact begins as friendly to you and will assist you with matters related to their criminal endeavours.

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 travellers 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 favour.
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. Additionally, you have a sizable group 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 can 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 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.

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Burglar

Burglars break into and steal from houses, storefronts, and warehouses, primarily operating out of major cities and ports. While thieving is a risky pursuit, the hardest part can be finding a buyer for rare and valuable items. The more unique the good, the more likely its original owner will want it returned, cutting your profit margin considerably.
Goods and valuables generally need to be sold through a fence: someone who will purchase your stolen goods, sell them to unknowing customers, and take a cut of your profits.
Skill Proficiency: Perception.
Additional Equipment: a grappling hook and rope, kidskin gloves, glass cutter, a vial of flour.

Surveillance

Upon spending an hour observing it, and succeeding on a DC15 Wisdom (Perception) check, you can map the general layout of a building. This includes the guard routes and rotation times, building entrances and exists, and the potential locations of valuables.

Rank 1 - Snatcher

Breaking into homes in the lower end of town is generally your trade. Authorities only worry about civilians with the power to cause a stir; everyone else is on their own. Locks in this end of town are easy to pick, if there is a lock at all. For the same reason, though, there is less to steal.
Holdings:

• A safehouse in the poor district, used to store stolen goods and serving as emergency lodgings.
• You have blueprints of a grand estate including secret entrances and passageways.

Progression: You rob a well-to-do store in a reputable district, gaining notoriety and a big payday.

Rank 2 - Burglar Specialist

Working in a team, while risky, allows for heists that would be beyond the reach of any one burglar, no matter how skilled. Increasingly, when someone has an ambitious crime planned and needs to assemble a team of "the best," they reach out to you.
Holdings:

• A team of specialist thieves who operate under your instruction to execute more ambitious heists.
• A contact working inside an establishment which you plan on robbing, who provides you information on the routine of the occupants, the location of valuable items, and escape routes.

Progression: Membership in an established Thieves' Guild in a major city or town.

Rank 3 - Heist Master

Your skill as both a burglar and a leader has grown considerably over time. Whether by virtue of your own confidence or a message from the divine, you believe that you are capable of executing a major heist, with the right preparation and henchmen of course. Will it be a priceless painting you have been tasked with acquiring for a prospective buyer? A slovenly prince whose private affairs you seek to meddle in, having acquired his signet ring?
Holdings:

• You hold a senior position in the Thieves' Guild, instructing junior members on lockpicking, housebreaking, and evading law enforcers.
• You uncover evidence of an attempted assassination on the life of a noble whose estate you robbed.

Progression: You orchestrate a large-scale heist to rob the estate of a local noble.

Rank 4 - Prince of Thieves

You have squirreled away enough gold to live comfortably for the rest of your life. However, you now steal to satiate a greater motivation through the exchange of private information, blackmail, and the acquisition of rare and powerful artefacts. After all, knowledge is power, and you've risen to a level where power is mandatory.
Holdings:

• Your own estate with a household of staff, acquiring and selling rare and valuable items through you own circle of thieves, fences, and buyers.

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