Rogue Archetype - Thug

Subtlety in the criminal world is often assumed to be the standards for those who operate outside the law. However there is a place for those who are more upfront provocateur's who are the muscle of these groups. While lacking in discipline they have found a way to use their more brutish approach to lucrative effect. 

When you first gain access to this archetype you gain proficiency in intimidation if you don't already have it and you can substitute strength for charisma when adding a modifier to the roll. Whenever you socially interact with a character that you are not currently in combat with, you may roll an intimidation check against an insight check. If they fail the save by 5 or more you take prof * d6 worth of gold from them if they can afford it, for you to leave them alone. 

When you first gain access to this archetype you gain proficiency in Medium armor and one martial weapon of your choice. Additionally your sneak attacks can be done with non-finesse weapons. You lose the ability to deal sneak attack with ranged weapons. Additionally you gain proficiency in Strength saving throws and can substitute dexterity saving throws with Strength. This comes from a lifetime of dealing with the physical abuse of working as a hitter for the criminal underground. 

At 9th level you are infamous for your heroic or criminal deeds. You have advantage on social checks if you spend at least 48 hours in an area and either spread word of your deeds or people know who you are in the area.

Additionally powerful individuals may offer to pay you additionally for your protection during downtime. Your going rate is your shakedown rate * 1d10. You can only offer protection in 24 increments at a time and depending on what events are taking place. Powerful individuals may offer additional rewards depending on your standing with them. 

At 13th level your infamy continues to grow and any criminal organization with the ability to communicate effectively knows of you. When you attack a creature that is sentient for the first time roll an intimidate against a charisma saving throw. If the target fails the same you have advantage on that creature for the rest of combat. If the target is immune to fear effects it cannot be affected by this ability.  

When you reach 17th level in rogue, you are familiar with the rules of any criminal organization you can communicate with (share a common language). When you come upon any structured organization and can see a member in a leadership position you can "call them out" with an intimidation check against their insight. If you succeed the check, all other creatures cannot focus you except the leader. If you defeat the leader before the followers are defeated, you may use a free action to announce your victory and demand that the rest give into your rule. Roll another intimidation check against insight. If you succeed you can provide any reasonable direction for the followers to take. Additionally you can take on one creature as your "Right hand man" as long as you can communicate with them.