Syndicate

Organized crime subclass. Lawful based rogue at the heart of the guild. They are somewhat like a bardic version of the Arcane Trickster. Mobsters, corrupt politicians, smugglers rings, etc. They put the organized in organized crime. They are always lawful, though not nessisarily evil. 

NOTE: This character is a 1/3 caster (not a half caster) but the system did not give me that as an option. 

Level 3: Trust Me...

 

You gain two additional skill slots for charisma based skills but sacrefice some of your choice of character development later. As you gain levels in rogue your charisma based skills will take more of a prominant roll. Thus, at 6th level when you again have the chance to chose skills for expertise, you can only choose from the charisma based skills. This shows the level of work that you have been putting into the charisma based skills and thus this subclass. 

Level 3: Charismatic Casting

For figuring out spell slots, use the spell level progression of Arcane Tricksters in the Players Handbook. At 3rd level they start with two cantrips and a single first level spell slot. The spell casting ability used for their spells is Charisma, the same as bards. Rather than singing and playing instruments, syndicate are trained in giving speaches that move the emotion and empower desire. 

Level 9: No secrets too small

As a bonus action you can attempt to either persade or indimidate others. You have honed your skills to the point that a few words and a well placed eyebrow convey more meaning than most people can in full lectures. You can also use these skills in place of insight or investigation when dealing with others. The person that you are speaking to must be intelligent enough to understand both you and the language that you are speaking in. You may drop a name here, flash a knife there or just reference a bit of information that makes the person think that it is safe to tell you information. Foes in combat are immune to this ability as they are already hostile and thus guarded toward you. 

Level 13: Poweer and Influence

You have gotten to a high enough position in your organization that you can use your influence to alter the way people interact with you. In towns where you are considered a local, you rarely pay for meals and can ask politicians for favorable rulings. People consider you noble class, or at least as good as a noble when dealing with you. When outside of your normal sphear of influence you may take a little longer to find a person who can make things happen in the way that you want, but the smaller the issue the faster it can be resolved. Work with your DM when utilizing this feature as the syndicate stirs.

Level 17: The Boss

When the boss is unhappy some may lose their jobs, some may lose their lives. You are at the point where you can choose to make a possition of power for yourself. You have influence over people in power and if you choose you could also be the puppet master pulling the strings behind those who make decisions. A favor from you is worth more than gold, and is coveted more as well. Work with your DM to take charge of the vast influence that your syndicate has.