Criminal Background 5e Guide: Living on the Wrong Side of the Law

Whether you’re selling stolen goods out of the back of a cart, smuggling contraband across heavily guarded borders, robbing banks on the frontier, or make your living some other way that’s outside the confines of the law, the Criminal background is a great way to flesh out any rogue (or other character with a past as a career crook for that matter) in Dungeons & Dragons 5e.  

The Criminal 

Skill Proficiencies: Deception, Stealth

Tool Proficiencies: One type of gaming set, thieves’ tools

Equipment: A crowbar, a set of dark common clothes including a hood, and a pouch containing 15 gp

Feature: Criminal Contact

In your time spent operating outside of the law, you’ve managed to cultivate a reliable, trustworthy contact in the criminal underworld. This person will liaise with criminal factions, other individual criminals, and help you fence stolen or illegal items.

You likely have a secret way of getting in touch with your contact, even over great distances, and know how to find suitable messengers in any backwater gambling den, dive bar, or other establishment of ill repute. 

 

Before taking up the adventuring life (and maybe even after – old habits and all that) you made your way in the world as a career criminal. Sure, everyone’s misreported their taxes or stolen a horse for a joy ride at some point, but people who commit crimes and Criminals are different breeds altogether. 

You’ve spent an extensive amount of time integrating yourself into the criminal underworld – whether that means you’re known to thieves’ guilds in every city up and down the sword coast, or just the go-to smuggler, petty thief, or stolen art dealer in the small town where you grew up.

Regardless, you know the social cues, tricks of the trade, and have friends in low places. 

Until now, flouting the laws and codes of “civilized” society has served you well, even if it’s put you in closer proximity to acts of murder, theft, and violence than most people feel comfortable getting.

Regardless of what changed to prompt you to take up the adventurer’s mantle, a life of crime casts a long shadow. In your heart of hearts (if not on every wanted poster from Waterdeep to Neverwinter) you’ll always be a criminal. 

How do I play a Criminal? 

The Criminal background is one of my favorites in the Player’s Handbook. Given the fact that the difference between graverobbers, thieves, bandits, murderers, and outlaws, and a noble party of adventurers is largely an issue of branding, it’s a background that fits neatly into a D&D character – especially if you keep finding illegal or cursed items in dungeons. 

How you choose to play your Criminal is entirely up to you. Do you want to be a daring sneak thief like Catwoman or Lupin? A fast-talking wheeler-dealer always on the lookout for the next score?

A streetwise thug who knows it’s easier to go through someone’s pockets when they’re dead? Maybe you have a penchant for flat caps and an insatiable drive to make your street gang (say, a mob of wererats called the Squeaky Blinders, for example) the rulers of this here town. 

However you choose to flavor your Criminal character, proficiency with thieves’ tools is going to make you adept at cracking safes and breaking into locked rooms, and you can likely use your proficiency with a gambling set of your choice will help you feel right at home at back room poker nights and underground mahjong parlors. 

Criminal Specialty

Whether they operate within different departments of a thieves’ guild, a gang, or work alone, there are many different sorts of criminal, with different skills that lend themselves towards pulling off different criminal capers. 

When you create a Criminal, choose the type (or types) of crime in which you specialize, either from the list below or by making up your own. Keep in mind that some of the more “soft” types of crime like confidence trickery and fraud may mean you’re more suited to the Charlatan background instead. 

d8Criminal Specialty
1Blackmailer
2Burglar
3Enforcer
4Fence
5Highway robber
6Hired killer
7Pickpocket
8Smuggler

Suggested Characteristics

Criminals have some of the most interesting and dramatic Personality Traits, Bonds, Ideals, and Flaws of any Background. Choose from the list below or invent your own. 

d8Personality Trait
1I always have a plan for what to do when things go wrong.
2I am always calm, no matter what the situation. I never raise my voice or let my emotions control me.
3The first thing I do in a new place is note the locations of everything valuable—or where such things could be hidden.
4I would rather make a new friend than a new enemy.
5I am incredibly slow to trust. Those who seem the fairest often have the most to hide.
6I don’t pay attention to the risks in a situation. Never tell me the odds.
7The best way to get me to do something is to tell me I can’t do it.
8I blow up at the slightest insult.
d6Ideal
1Honor. I don’t steal from others in the trade. (Lawful)
2Freedom. Chains are meant to be broken, as are those who would forge them. (Chaotic)
3Charity. I steal from the wealthy so that I can help people in need. (Good)
4Greed. I will do whatever it takes to become wealthy. (Evil)
5People. I’m loyal to my friends, not to any ideals, and everyone else can take a trip down the Styx for all I care. (Neutral)
6Redemption. There’s a spark of good in everyone. (Good)
d6Bond
1I’m trying to pay off an old debt I owe to a generous benefactor.
2My ill-gotten gains go to support my family.
3Something important was taken from me, and I aim to steal it back.
4I will become the greatest thief that ever lived.
5I’m guilty of a terrible crime. I hope I can redeem myself for it.
6Someone I loved died because of a mistake I made. That will never happen again.
d6Flaw
1When I see something valuable, I can’t think about anything but how to steal it.
2When faced with a choice between money and my friends, I usually choose the money.
3If there’s a plan, I’ll forget it. If I don’t forget it, I’ll ignore it.
4I have a “tell” that reveals when I’m lying.
5I turn tail and run when things look bad.
6An innocent person is in prison for a crime that I committed. I’m okay with that.

Variant Criminal / Spy: Spy

If you want to utilize the skills of a Criminal but like the idea of acting on behalf of a slightly more “legal” organization, the Spy variant is a great choice that lets you put all your sneaky, socially slippery talents to other uses. 

You might have worked as an espionage agent behind enemy lines during a cataclysmic war, a guild operative working to infiltrate rival factions or any other clandestine character that intrigues you.