People often think of rogues as coming from the lower strata of society, but the upper crust is just as capable of viciousness, duplicity, and skulduggery as those with less privilege. Indeed, they are often worse, for the poor thief operates out of desperation whereas the wealthy assassin works purely out of self-interest. A rare few, however, put their Machiavellian skills to noble purposes, pulling the levers and strings of power to provide for and protect the vulnerable in their society.
At 3rd level, you learn the skills to fit in with the aristocracy. You gain proficiency with the Culture skill or an expertise die if you are already proficient. Your maximum expertise die size for the Culture skill increases to a d10. You also gain the etiquette specialty for the Culture skill or a different Culture skill specialty if you already have it. Finally, you gain proficiency with two choices from the following list: forger’s kit, calligrapher’s tools, painter’s tools, Medicine, History, or a musical instrument.
Also at 3rd level, your poise and bearing bring with them the privileges of the highborn. You are treated as if you have the High Society feature from the Noble background. If you already have it, you gain +1 to your Prestige score instead.
Finally at 3rd level, you may maintain a pleasant facade, but once the mask slips, you are terrifyingly brutal. You gain proficiency with your choice of the Viper’s Fangs or Grinding Cog combat tradition. You also learn a maneuver from your selected combat tradition of a degree you could learn. It does not count against your maneuvers known.
At 9th level, your social connections allow you to pull the strings of high society. When you are in a community of at least 200 people, you can spend an hour sending messages or meeting with contacts to call in a favor. Choose one of the following options:
Once you have used this feature, you can’t do so again for a week, and you can’t use the same option twice in a row.
Also at 9th level, you have a small network of sources that constantly drip-feeds you juicy rumors. You gain advantage on checks pertaining to the Gossip journey activity and Gather Information downtime activity.
Finally, at 9th level, your connections provide you with training and equipment not available to just any old guttersnipe. You gain proficiency with a rare weapon of your choice and also receive such a weapon free of charge.
At 13th level, you can hit someone from the upper classes where it hurts most: their social standing. To do so, you must spend a day spreading salacious rumors about your target, who must be a noble, royalty, or another person of significant wealth and status. Make a Deception check against the target’s CR + 10. If the check is successful, the target suffers two levels of strife from the stress and has disadvantage on all Persuasion, Insight, and Deception checks for the next week as they and their people do frantic damage control. If the rumor you spread is true, you have advantage on this check.
Also at 13th level, you have learned to cover up the evidence of the violence you do. If you kill a creature without being observed and can spend 10 minutes with the body and crime scene before being discovered, the death will appear to be an accident on any Investigation check short of a critical success. Even on such a critical success, all the investigation reveals is that the target died via foul play; it does not implicate you (or anyone else) in the death automatically. This feature also renders the body unable to answer a speak with dead spell and attempting to uncover the actual cause of death via other magical means requires the caster to make a spellcasting ability check against a DC of 8 + your proficiency bonus + your Intelligence modifier.
At 17th level, you can move heaven and earth to accomplish your goals. You can use Pull Some Strings once per long rest. In addition, the temporary followers you get from Pull Some Strings are now experts instead of seasoned (if applicable).