You've come to be known locally as a ne'er-do-well, a ruffian, perhaps a rapscallion of sorts. Perhaps you've extorted a local politician, kidnapped a rich maiden for ransom, or bullied local merchants into paying for your protection. 

Most importantly, you've never rarely stooped to simple robbery and thieving; instead, you prefer a more flashy approach to villainy. Your plans are often complicated and have plenty of opportunities for things to go wrong, which they often do. Perhaps this is all a part of your secret desire for redemption? Or perhaps you are so certain of your success that you are simply trying to keep things interesting.

Skill Proficiencies: Sleight of Hand, Intimidation

Tool Proficiencies: Choose two from the following: Disguise Kit, Forgery Kit, Poisoner's kit,  Thieves' Tools, or any Gaming set

Equipment: A dagger, 50 feet of silk rope, one type of tools that you are proficient in, a set of common clothes, and a pouch containing 15 gp

Suggested Characteristics

As a villain, you maintain a sneering and greedy persona most of the and put your self (as well as your bad reputation) above all else.

You may or may not have a heart of gold (or tarnished silver). You may occasionally join heroic quests out of a secret desire for redemption or simply for the glory. 

d8	Personality Trait
1	My friends know they can rely on me, no matter what.
2	I work hard so that I can play hard when the work is done.
3	I enjoy sailing into new ports and making new friends over a flagon of ale.
4	I stretch the truth for the sake of a good story.
5	To me, a tavern brawl is a nice way to get to know a new city.
6	I never pass up a friendly wager.
7	My language is as foul as an otyugh nest.
8	I like a job well done, especially if I can convince someone else to do it.

d6	Ideal
1	Respect. The thing that keeps a ship together is mutual respect between captain and crew. (Good)
2	Fairness. We all do the work, so we all share in the rewards. (Lawful)
3	Freedom. The sea is freedom — the freedom to go anywhere and do anything. (Chaotic)
4	Mastery. I’m a predator, and the other ships on the sea are my prey. (Evil)
5	People. I’m committed to my crewmates, not to ideals. (Neutral)
6	Aspiration. Someday I’ll own my own ship and chart my own destiny. (Any)

d6	Bond
1	I’m loyal to my captain first, everything else second.
2	The ship is most important — crewmates and captains come and go.
3	I’ll always remember my first ship.
4	In a harbor town, I have a paramour whose eyes nearly stole me from the sea.
5	I was cheated out of my fair share of the profits, and I want to get my due.
6	Ruthless pirates murdered my captain and crewmates, plundered our ship, and left me to die. Vengeance will be mine.

d6	Flaw
1	I follow orders, even if I think they’re wrong.
2	I’ll say anything to avoid having to do extra work.
3	Once someone questions my courage, I never back down no matter how dangerous the situation.
4	Once I start drinking, it’s hard for me to stop.
5	I can’t help but pocket loose coins and other trinkets I come across.
6	My pride will probably lead to my destruction.