Roleplaying a Criminal?

[CrazyCrab]

Hi everyone,
IRL I'm as lawful as they go, so I figured that playing the opposite will be quite fun.

I have a character in mind, but I'm really not sure as to how I can play them in an interesting fashion - I'm thinking of a "reintegrating" criminal. A guy who's been a crime boss all his life, think a Godfather of the Forgotten Realms, but eventually made a mistake and (personally) caused the death of an innocent child. Deep inside he isn't really that bad of a buy, so, heartbroken, he gives in to the authorities, donates all of his unlawful proceeding to a charity, goes to prison. 30 Years later, he's free once again and this time he wants to make things right. Knowing no trade other than how to kill, he becomes an adventurer.

How does being a criminal affect your average adventurer? Any tips on playing them in an interesting fashion? I obviously don't want to be that rogue who "Can I sleight of hand the party" and "I pocket the loot before the party gets there". He really wants to be a good guy, but maybe is having difficulties adjusting, any tips on that?

Thanks!

[Pleh]

You probably have a lot of connections in the criminal network, even though your reputation has gone down the tubes. It might take some pushing and pulling here and there, but anything you want to learn about what's going on in town (that the police don't know about) you probably know who it is that does know and some idea about how to find them.

You also are likely very familiar with the local legal system and nuances of the laws of the land. You know what conduct is bending the rules as opposed to breaking them outright, and where the best loopholes are.

That said, you probably have an equally unsavory reputation with the good and legal side of society. People are more likely to know your name and associate it with your known crimes, even if you claim you don't do that anymore (yeah, sure...).

You're probably familiar with black market goods and prices to some degree. You can probably recognize readily common products that have to be smuggled or fenced to elude legal control measures.

You are likely very charismatic and crafty. The Godfather style criminals express a very classy form of criminal nature built on mutual respect and courtesy. You're not afraid to get your hands dirty, but you might be more inclined to intimidate your opponents into compliance so violence isn't necessary. Where intimidation doesn't work, often a small bribe might do the trick.

You say you're a lawful type. Lawful types can make the best criminals. They just operate on their own sense of law:
"You cross me, I'll make you regret it."
"I never break a promise, especially threats."
"Do this job for me right, and I'll reward you handsomely."

Often these types of criminals are really very lucrative businessmen who aren't necessarily chaotic in nature. They're lawful, just they abide by their own intuitive sense of rules and manners. It's bad business to be unreliable or too spontaneous like those chaotic whackos.

Bottom line: You want a Rogue focused on Social/Diplomatic skills with an emphasis in Intimidation. You've got the murderous skills to back your threats up with force if necessary, but your real power is in how you influence other people.

[NRSASD]

Pleh's got the right of it. An interesting angle to play up would be struggling not to solve problems the Godfather way. Your character can make that annoying guard captain (and her family) disappear if she crosses you, but doesn't want to resolve things that way. You know the best way to poison a drink and coerce your rival's cooperation, but why can't we resolve our differences diplomatically? The option to solve the problem quickly and brutally is always there, but you're trying to be the better person and not give in to your instincts.

As far as playing your character, I'd go with a kindly, well dressed old man, one who's always helpful and advocates restraint. After all, it's been 30 years in the clinker and he served his time fair and square, so he's probably dropped off the police's radar. The rest of the party should have no idea that your character was a criminal, much less that Godfather, the one whom people still tell tales of his cunning and vicious practicality.

[Aliquid]

Any tips on playing them in an interesting fashion? I obviously don't want to be that rogue who "Can I sleight of hand the party" and "I pocket the loot before the party gets there". He really wants to be a good guy, but maybe is having difficulties adjusting, any tips on that?He might want to be a "good guy", but maybe he has a hard time grasping who the "bad guys" are.

"Hey, I'm working with a group of 'good guys', and this person is in our way... therefore, he must be a 'bad guy' that we need to deal with"

As NRSASD suggested, the guard that is stopping you must be dealt with... maybe he has an accident.

But at the same time, you can be overly and naively sharing with your party rather than "pocketing the loot before they get there". You could say "Since that merchant was such a jerk to us, I lifted a bunch of stuff from him. I stole this for you, and this for you.... "
When the other characters say "Wait you did what?", he can look baffled... "but the merchant was a jerk, and I'm sharing... what's the problem?"

[Vogie]

Another option is going playing off the themes of "The Blacklist" - You're actively using both the law and your criminal contacts to get rid of the worst of the criminals. This may also be to your advantage.

You don't have to play a thief, or even a rogue. You could be an ex-enforcer, a rider/driver/courier, a smuggler, charm-wizard conman, a networking bard, even a Bladepact Warlock who had to turn themselves in because no one could find the murder weapons.

As you've already done your time, depending on the world you're in, you may have to keep papers on you that show that your debt to society has been paid. You may run into guards with a grudge, or other criminals that used to be part of the posse of your character. Depending on how fast news spreads in the area, the character may still be thought to be at large, even though you've been through the prison system and done the appropriate amount of time.

[Berenger]

I wouldn't make him a godfather / crime boss. These people wreck the life of innocent persons including children all the time and have to be smart enough to realize this to be smart enough to manage their operations successfully. One of them freaking out over the death of a single child isn't something I personally would find believable - unless this child is somehow special (for example because the child was part of the criminals own family). Also, if you were part of a criminal society for most of your life, turning yourself over to the authorities seems like a strange way of atonement because this requires a sudden change of your fundamental disregard for society and lawful principles and institutions in addition to sudden guilt.

For your concept, I'd pick a character that's more nonviolent and in over his head than a mob boss, a small-time criminal like a conman, pickpocket or burglar, possibly also a drug addict. All of them can cause a death by accident or as a by-product of their crimes, for example by depriving a childs parents of the means pay for a doctor or by knocking down an oil lamp and causing a home fire during a botched housebreaking.

Also, both the idea of lenghty prison sentences and the goal of "reforming" criminals are ultra-modern approaches as far as historic penal systems go, far ahead of the periods most often used as inspiration for "medieval" rpg settings. Make sure to check with your GM what the expected punishment for your characters crimes would be and whether it matches with your backstory or not.