Gentleman Spy Image

You understand wealth, power, and privilege. You carry a noble title, and your family owns land, collects taxes and wields significant political influence, but neither the simple life of a pampered lordling or the audacious pomp of a politician sat right with you. Your skills and desires leaned to more "real world" pursuits. 

Whether through bribery or nuanced negotiations, you maneuvered yourself deep in the throes of spycraft and/or straight forward criminal activity. Through guile and perseverance, you found yourself playing a beautiful game of subterfuge and intrigue. You have spent a great deal of time among criminals, politicians, nobles and, more importantly, all of the underlings that attach themselves to such positions. While you’re far closer than most people to the world of murder, theft, and violence that pervades the underbelly of civilization, you have survived up to this point by both deftly flouting, and exploiting, the rules and regulations of society.

 
Skill Proficiencies: Deception, Persuasion
Tool Proficiencies: One type of gaming set
Languages: [language]Thieves’ Cant[/language]
Equipment: A crowbar, a signet ring, and a purse containing 20 gp
 
Feature: Overworld Contact

 It is said for each lawful or "proper" organization there is an unlawful one to match.  Through your years navigating all each side of society, you have developed an aptitude for finding groups in both.

In an environment where you are familiar (town, city, country) you will have minor contacts to both noble houses and criminal organizations, however anyone from those groups who do not know you well will be wary of you simple because of vague rumors about your activities.

In an environment you are not familiar with, you have a better time than most in discovering, and possibly interacting with, organized seats of power regardless of their legal status.

 
Suggested Characteristics

Nobles are born and raised to a very different lifestyle than most people ever experience, and their personalities reflect that upbringing, however your time amongst the servants of the world and the dregs of society has tainted your pristine lineage. Because of this, you maintain a slightly nefarious or scandalous reputation with people who are familiar with you, regardless of which part of the world they are from. Some nobles might be repulsed by rumors of you consorting with the wrong folk, while others might be drawn to your adventurous spirit.  Some criminals might be weary of your obvious connection to wealth and lawful power, while others will see kinship in one who purposefully bucks their station in life.

 
Gentleman Spy Image

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