Reformed Criminal Image

You walked the mean streets as a younger person. Whether it was for money, necessity, or just the thrill of it, you lied, cheated, stole, and perhaps even killed. But as you matured, you realized that the criminal life wasn't for you. Maybe you knew too many people who were caught and severely punished. Or perhaps a wise, compassionate soul guided you back to the straight and narrow path. In any case, you've left those dark days behind you, and you hope that life as a legitimate citizen has better things to offer you.

 
Skill Proficiencies: Insight, Perception, and either Investigation, or History.
Languages: Theives' Cant
Equipment: You carry with you the last of the wealth you garnered through illicit means: A pouch containing two small gems (10 gp each), one platinum coin, and 10 gold coins.
 
Feature: Back on the Right Side of the Law

Even though you've given up your lawbreaking habits, you still carry with you abilities learned in carrying out criminal acts. You gain advantage on ability checks to oppose another character's Deception and Sleight of Hand rolls. You also know where the criminal elements in a city are likely to reside. This knowledge is best used to avoid such areas, because if anyone in those places knows or has heard of you, they won't take kindly to your abandonment of their ways.

 
Suggested Characteristics

Following societies laws after flouting them for so long isn't easy. But you try your best. Hopefully you won't run into anyone on either side of the law who carries a grudge. In any case, the past is the past, and you need to look forward. You have places to go and things to do.

d6 Personality Trait
1 I'm not paranoid if there really are thieves, assassins, and worse who are trying to kill me.
2 Now that I've turned a new leaf, I feel unburdened, carefree, and happy.
3 I must earn the trust and respect of those I like/admire.
4 I will starve before I steal what rightfully belongs to another person.
5 I may no longer be a criminal, but I can still sympathize and empathize with the social conditions that force many unfortunate souls into that lifestyle.
6 I may no longer be a crook, but that doesn't mean I have any love for sheriffs, constables, city guards, and other oppressors of free will.
d4 Ideal
1 I must make up for all the harm I caused others. (Good)
2 No clan, guild, or boss of any kind can tell me how to live my life. (Chaotic)
3 Law and order must be respected if society is to thrive. (Lawful)
4 The world and all its possibilities are open to me. (Neutral)
d4 Bond
1 Though I've left them all far behind, I cannot escape the debt I owe my former comrades.
2 I must keep secret and safe the underground railroad that helped me escape my former life.
3 It is my duty to help others reform and rehabilitate themselves.
4 I must never judge too harshly any thief or criminal, for I know all too well the temptations that drive them.
d4 Flaw
1 Humble and penitent as I try to be, I can't help but look down at those who live the life I used to.
2 Shadows and what may lurk within them give me an awful fright.
3 Even though I have nothing to hide (any more), I find myself sticking to the shadows and trying to avoid any attention given to me.
4 My strong desire to atone for my misdeeds have given me quite a martyr complex: I feel compelled to face any danger I may encounter, regardless of whether or not I'm up to the task.
 
Reformed Criminal Image