3 Questions For Fleshing Out Criminal Characters

Every party has one. Well, at least one. You know, like the burly former captain who always pulls up his hood when guard patrols walk by. The light-fingered mountebank with that tattoo she's always trying to keep hidden. The halfling who seems to know just a little too much about how locks work, and how to sweet talk them open. Even the woodsman, whose knowledge of branding techniques is pretty extensive, and whose running iron appears to have been used in more than one fire.

He sure does know a lot about tying up struggling women... just saying.

While stalwart heroes often heed the call to adventure, there are an even greater number of unscrupulous rogues, black-handed villains, vicious bandits, and cold-blooded assassins who make their way into our adventuring parties. If you don't want your criminal PC to feel like just another random thief, though, then you should ask what made them into a criminal in the first place? And what made them stop... if, indeed, they have stopped?

And if you're looking for old friends, unique gangs, or even legendary bandit captains to tie your character to, you might want to check out 100 Random Bandits to Meet, written by yours truly for Azukail Games.

Part One: What Do You Get Out Of It?

There are a lot of reasons to play PCs who are criminals. Maybe you just don't like classic heroes, so you want to play someone who's got some dark spots on their record. Perhaps you're using it as a way to justify the particular set of skills your character has. Or you might just feel that the law is an inconvenience, and you're more concerned with getting results than in what methods you used to get them. There are plenty of reasons to play characters who are, or who were, criminals.

However, it's important to ask what got your character started down that road, why they did or didn't turn off that path, and how that jives with what they're doing at this point in their lives.

You call it theft. I call it freeing slaves.

There are a lot of factors that can lead someone to becoming a career criminal (since that's typically what we see at our tables when discussing criminal PCs). The first, and most important, is asking what they get out of it?

The most obvious answer tends to be profit. You were a sailor, and when you were discharged you had no viable skills for civilian life. So you assembled a crew, and you all turned pirate, bringing down merchant vessels and trading ships, emptying their holds to fill your pockets. However, there are reasons to become a professional lawbreaker other than gold. Perhaps you were born with a silver spoon in your mouth, but the thrill of thievery turned you into a gentleman thief. Maybe you kept what you took as a trophy, or gave it away to the needy, but what you stole isn't what mattered. It was the rush you got from the theft. Maybe you committed your crimes because if you wanted to stay safe in your neighborhood, then you had to run with one of the gangs that controlled the area. So you might not have realized anything in the way of profit, but you got protection, approval of your friends, and built a kind of family among your crew. Maybe it was just tradition. Something you were born into as surely as you had dark hair and blue eyes.

Part Two: What Did It Cost You?

Once you know what someone got out of being a criminal (whether it was money, security, family, or just fun), the next question you should ask is what did they have to overcome to do it? Or, put another way, what did being a criminal cost this PC?

The ability to wear collarless shirts, perhaps?

This one can be a lot to unpack, depending on your character. For example, say you had someone who became a pickpocket for the Red Brand Boys out of a need for protection. As he grew older, and bigger, he became a hatchet man. He fought, and he killed, in the service of his gang. He earned his colors. But how many friends did he see buried because of turf wars? How many times did his boss put his life at risk for stupid reasons, costing him a hand, an eye, or a leg in his service? Did the respect he got from his brethren stop outweighing the fear he saw on other people's faces? Did his reputation make family members turn away from him, or get a lover killed to send him a message?

That's the best-case scenario. Unfortunately, when you're an outlaw, stuff can always go wrong. For example, take the gentleman thief. Did he get caught? Did being caught lose him his title, or land? Has he been disowned, forced to rely on his skills and his wits? Or, worse, was he treated like a common thief and punished publicly for his crimes? Did your bandit get captured, and so he opted to do a stint in the army rather than face the rope? Are there angry nobles looking for your conman who swindled them out of entire fortunes, which has made him give up his name, his life, and even his home nation in order to stay one step of the hunters?

There are all kinds of costs you pay when you gamble on criminal enterprises. How often have your PC's pips come up snake eyes?

Part Three: Are You Still A Criminal?

So, you now know why you became a criminal in the first place. We know what it cost you to live that life. Now you need to ask if your character is still a criminal, and if not, what made them leave that life behind?

I made that last score. I'm done, now.

Characters grow and change all the time. For example, being a neck breaker for an organized crime family might not really gel with accompanying a paladin and his squire into the wild lands in order to raid a dungeon. However, let's say your enforcer met a woman, and her condition for marrying him was that he get released from his bond to the Black Brotherhood. So he left, and never looked back. Now he's got a wife, and a child on the way, and he wants to be able to provide a good life. So he agrees to accompany the knight and his hangers-on for a share of the loot to be found in the necromancer's tomb. After all, dead men had no need for gold, and whatever lurked down there couldn't be any darker than the deeds he'd already done.

Or, perhaps, that enforcer never left the Brotherhood. However, his street commander told him to tag along, and watch the knight's back. Why? Maybe it's as a favor to someone. Maybe it's because the paladin never interferes with this town's running, and the mob doesn't want that to change. Maybe it's because someone in the group inquired, and where there's ruins, there might be loot. Stealing from dead men is often easier than stealing from live ones, and an easy score is never something to turn down.

There's no right or wrong answer to part three, but it does bear thinking about because your character's current criminal status could affect the rest of the party. Of course, it's possible that you're all criminals, which is why you're "adventuring" together in the first place.

This Isn't About Good, or Evil

It's important to note here that we're talking specifically about criminals, not necessarily about evil characters. Because while that can play into some of these questions (such as an assassin who accepted an atonement spell, who then became good-aligned and left their old ways behind them), it's important to remember there are several types of heroes who are technically criminals. Robin Hood is the iconic example, stealing from corrupt tax officials and the rich in order to give the poor enough to live on. Those who free slaves through violence are often seen as freedom fighters, but the nation who allows slavery would see them as little more than thugs and brigands. And, of course, someone who steals, transports stolen goods, or sells illicit material out of a necessity rather than out of maliciousness is often seen as at least sympathetic. Especially if they're just looking for a way out of the life they've been forced to lead.

However, if you've decided your PC is (or was) a criminal, put some thought into it. What kind of criminal were they, what did they get out of it, and why did they stop? Or if they never stopped, then what keeps them going? Is it habit? Need? Or just being unable to live a regular life after being this person for so long?

That's all for this week's Moon Pope Monday update. Hopefully it greased the wheels, and gave some folks new character ideas. If you'd like more content from yours truly, check out my Vocal archive, or head on over to Dungeon Keeper Radio where I and several other games offer advice, tips, and a few laughs straight from the world of Evora. If you want to stay up-to-date on my most recent posts, then follow me on Facebook, Tumblr, and Twitter. Lastly, to help support Improved Initiative, head over to The Literary Mercenary's Patreon page to toss a little love in my cup. All it takes is $1 a month to make a difference, and to get some sweet gaming swag as a thank you!