Mafioso

Not all rogues work by themselves; some cultivate a family of underlings. They are the crime bosses, the head of these families that work as your information network. However, building a family takes time and trust and a healthy dose of fear and money.

Rogues of this subclass are master planners and confident in their intimidation and deception skills. They are almost akin to royalty to the underground. The best of them are considered untouchable.

Hide in Plain Sight

Your ability to hide amongst the people is unparalleled. As a bonus action, you can Hide in a group of two or more people even if you are still in sight of another creature.

Brawler

A true rogue is able to stir up trouble anywhere with anything. You gain proficiency in improvised weapons and they count as finesse weapons for you. You gain proficiency in firearms if your DM allows it.

Regional Chief

Working with others is often more profitable than working alone. You have grown a small organization and now have three underlings who will help you with stealing and will take the fall if you are convicted of a crime. They will not die for you so be careful what you ask of them.

Right-Hand Man

Time spent underground has given you some influence amongst others in your field of work. Your organization grows in letting you get away with some crimes with either a bribe or some intimidation (DM’s discretion). You also get advantage on Deception checks on government officials.

Kingpin

None are higher than you nor do they hold power over you. Your organization grows yet again leading to you being able to get away with high-risk crimes. You get advantage on all Intimidation checks against government officials and your underlings. You can not be convicted of a crime and your underlings can be bailed out with a Charisma check of the DM’s choice. You may also frame someone for a crime with 2 weeks of planning and 100 gp.