Broker

Any old chump can buy from one thief, sell to another, and call themselves a fencer. But you understand that being an infamous broker requires a little more care and finesse. You are an expert at acquisition and dissemination: information, wealth, items of value and power. You can construct a web throughout the backbone of civilised society, and you know of every single thing of importance within that web - or you know how to connect them to it. People of interest, memoirs, exposés, keys to secure locations, powerful items, dark secrets, hidden plots: nothing escapes your eye, and you know exactly how to exploit everything you can get your hands on.

Tools of the Trade

Starting at 3rd level, you develop the skills required to thrive in your occupation. When you finish a long rest, you can choose to gain proficiency in one of the following skills: Deception, Insight, Investigation, Intimidation, or Stealth. You double your proficiency bonus for checks you make with that skill until you choose another skill with this feature. In addition, the skill you choose grants you additional benefits until you choose another skill:

• Deception. You have advantage on any check to successfully craft yourself a form of identification, writ of passage, or other Tiny item to get you in or out of a location.
• Insight. If you are attempting to determine the value of an item, you have advantage on the check.
• Investigation. If you are attempting to look for clues to a target’s location or about a target’s identity, you have advantage on the check.
• Intimidation. If you are attempting to intimidate a restrained creature, you have advantage on the check.
• Stealth. If you are attempting to hide within a crowd, you have advantage on the check. You also move at your normal speed through crowds.

Expert Assessment

Also at 9th level, you have interacted with so many people that you know exactly how to beat them. You can spend one minute studying a creature outside of combat, you can learn one each of the creature’s damage resistances, damage immunities, and condition immunities, all of the DM’s choice. Once you use this feature, you can’t do so again until you finish a short or long rest.

Expansive Connections

By 13th level, you have created a wide network of information that you can access at a moment’s notice. You can spend one minute to contact someone within that network, perhaps an informant or a guild you have worked with before, to deliver you additional information pertaining to a specific topic. If you do, the next time you make an Intelligence check about that topic, you can treat the roll as a 20. Once you use this feature, you can’t do so again until you finish a long rest.

Best in the Business

At 17th level, you are well-known within the underworld for being a master at collecting and disseminating information. Your features improve in the following ways:

• You can now pick two skills with your Tools of the Trade feature, gaining the associated benefits for both.
• When a creature is under the effects of your Expert Assessment feature, your weapon attacks against that creature score critical hits on a natural roll of 19 or 20.
• When you use your Expansive Connections feature to gain insight on a specific topic, you also have advantage on all Intelligence checks you make about that topic until you finish a long rest or until use this feature again.