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 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.
Skill Proficiency: Intimidation, Sleight of Hand
Languages: Thieves' Cant.
Tool Proficiencies: Thieves’ tools.
Equipment: A kidskin bag of loaded dice, a snuff box, a pocket watch that runs five minutes fast, Thieves’ tools, fake currency in a drawstring pouch to deter pickpockets, a set of dark common clothes including a hood, and 15 gp.

Underground Connections

Upon spending an hour asking around, and succeeding on a medium-DC 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.
Holdings: A hideout where you can seek shelter from the elements, and from local law enforcement.