Exploring the Criminal and Spy Background

Today we take a look at the Criminal background and its Spy variant. Based on nothing more than anecdotal evidence, I am confident to say that the Criminal background is the most popular one in D&D 5e.

Why? Well, for one you get two really excellent skills, Deception and Stealth, and you get proficiencies with thieves’ tools. These three things together mean you can give any character some rogue skills, or leave room for a rogue to expand their tool kit. This is a very attractive background for your party to have if you lack a stealthy trap-disarming/lock-picking skill monkey.

Check out past background articles here: Acolyte, Charlatan 

Barbarian Criminal 

It’s not hard to see a barbarian getting into trouble upon contact with civilization and being forced to acquire certain skills to make life a bit easier. A barbarian with the criminal background can take advantage of the stealth skill to give them the drop on their enemies, or to sneak past guards, providing beefy backup for the party rogue or ranger. 

Their natural disregard for authority sets them on a natural collision course with the law and authority. Your criminal contact can be someone that you met on your travels or a merchant that you’d often have contact with before leaving your tribe. 

With the spy variant, think about the cultural group you come from. A wood elf barbarian spy could be sent to investigate the younger races after 500 years of solitude. Barbarians aren’t necessarily uncivilized, just channel their anger into a brutal fighting technique. Maybe something like a half-orc spy sent by an orcish warlord to spot weaknesses in a human kingdom.

Here are some traits for your barbarian criminal:

Bard Criminal

A bard criminal or spy can really direct the character more toward its roguish qualities. Bards make perfect spies and criminals being natural performers and information brokers. Your bard could have a role as a burglar or perhaps as the one distracting the guards while the others sneak in. 

Bards have a powerful tool kit in their spell selection. This combined with the skills gained from this background create a potent combination for lots of espionage and backroom deals. Your bard’s goal could be to build a network of crime, a fantasy version of The Godfather.

One character concept that I have really wanted to play is a half-elf bard spy who is sent by an elven kingdom to investigate the humans. They struggle to fit in in either world and must find their own place in the world. 

Here is a table of personality traits for your bard criminal:

Cleric Criminal

A cleric with the criminal background could be a devotee of any one of the numerous gods of shadows, night, thieves or crime. They could feel like they are exceptions to the law because of their connection with the divine. 

A cleric who serves any of the chaotic neutral powers could also be a Robin Hood type, that fights to bring justice and tear down the powers of oppressive order. The main thing when considering your cleric criminal’s background is how did they get into the game? 

Perhaps they grew up in a rough neighborhood and have been trying to leave a life of crime behind after taking their vows. If you decide to go with the spy variant, is your cleric something like an inquisitor, dedicated to rooting out heretics and the profane from their organization. 

Here is a table of some personality traits for your cleric.

Druid Criminal

There is no more perfect criminal than one who can hide in plain sight. A druid with the criminal background can put their animal shape to good use and slip in and out completely unnoticed. Or it could be that your crime forced you to flee civilization where you tried to find redemption in service to restoring and healing the land. 

Your crime may have been a mistake or part of a larger arch of your character, reaching toward some greater goal, like power, wealth and influence. Perhaps your druidic skills were innate and you have found that they play into your designs on crime. 

Druids also make excellent spies, easily eavesdropping as a cat or bird. A gnome druid could serve as a broker of information, trading secrets for lore or gold. Your contact could be another druid or someone within the network of criminals you’ve come to trust. Defining this relationship and giving your character a distinct point of view of the contact can help you when roleplaying a conversation with them. 

Fighter Criminal

A fighter benefits a lot from the criminal background. It wouldn’t be out of place for someone to pick up mastery at a weapon fighting style while working for a crime ring. Perhaps your crime is instead related to the reason why you are now a sellsword; once you aspired to be a knight, but a terrible murder, or theft, or even treason now means that you are a common sellsword. 

Fighters are already front-line characters, so being able to pick locks will come very much in handy. It adds a new dimension to your character’s skill set both mechanically and for roleplaying. Why and how did you come by your criminal skills? What were the events that put you in contact with your criminal contact?

As a spy, you can go the route of a promising warrior recruited by a shadow organization, or perhaps you joined the intelligence service out of patriotism, or maybe a more selfish reason. Developing your connection to the wider spy network and how you feel about your role and the missions that are given to you can help you make in-character decisions as the game unfolds. 

Here are some fighter criminal personality traits:

Monk Criminal

A monk requires lots of discipline and practice to gain the skill of even the lowest level monk. Therefore if you chose the criminal background, consider how your skills as a monk factors into your life of crime.

Did the crime push you to join a monastery to seek repentance? Did you learn your skills from a master within a thieve’s guild? Or perhaps you never could master the more subtle philosophical teachings your masters tried to impart, and use your abilities for personal gain.

A monk spy immediately makes me think of a monk being raised in a monastery dedicated to creating spies and assassins. A ninja school basically. With the monk’s natural stealthiness and some complementary skills to infiltrate enemy strongholds, they offer a potent combination for many roleplay golden moments. What happens when you leave the assassin’s compound for the first time and discover the world is more morally gray than you were lead to believe?

Here are some personality traits for your monk criminal:

Paladin Criminal

A war-weary champion seeking redemption for a terrible crime. A two-faced proclaimer of righteousness whose hands are covered in blood. An ardent warrior for justice, holding the rich accountable. These are all archetypes that you can play into when combining a paladin with a criminal background.

Like the charlatan background, choosing the criminal background for your paladin requires you to consider how they were able to gain the training they needed to become a paladin while also gaining the skills as a criminal. They could have grown up on the streets or as part of a thieves’ guild before having a moment of conversion and trying to live a just life. They could maintain an empire of crime, using the church as a front. 

Your paladin’s relationship with their criminal contact can form potential story hooks. What happens when they call in a favor and force you back into the game? What do you risk whenever you reach out to them for information? Do you miss your life as a criminal or do you want to leave it all very far behind you?

If you choose the spy background, consider that you naturally have a great cover identity as a paladin, the ultimate paragon of truth and goodness. Nobody would suspect you as an agent on a mission for some political power. 

Here are some traits for your paladin criminal: 

Ranger Criminal

Rangers can make great criminals and the bounty hunter or monster hunter archetype that could best take advantage of the skills and contact that this background provides. It wouldn’t be uncommon for a beastmaster ranger to use their connection to their animal companion to help infiltrate and snag their quarry.

As with the other backgrounds, keep in mind how you came about your two sets of skills. What did you do to learn your ranger skills? Did you learn them while part of a thieves’ guild? Or were you recruited because of your skills?
As a spy, you would be a perfect fit to serve as an advanced recon scout in an army, or as an investigator for the king tasked with tracking down and apprehending malicious agents. Rangers are natural trackers and make perfect counter-intelligence operatives. 

Here are some personality traits for your ranger: 

Rogue Criminal

The rogue makes a natural criminal or spy. There is already a lot of overlap mechanically, so you can expand your skillset and give your rogue more options for gameplay. Rogues have a slightly easier job with this background as the life of a criminal lends itself to the abilities you acquire as a rogue. 

Therefore, flesh out your connection to the criminal underworld, your position in it. Who do you care about? Do you have any enemies? How did you make them? What are your goals with your criminal career? Do you want to leave or do you want to grow your power base?

Rogues as spies could be an ex-criminal who was recruited to do more state-approved work. Your reason for accepting it can range from greed to patriotism to not having any choice in the matter. Sometimes the best decision is the one that keeps you alive. 

Here are some traits for your rogue criminal:

Sorcerer Criminal

I would love to see a character who only discovered their sorcerous powers after living life as a criminal. They now have a leg up on all the competition and it would be cool to explore how the new surge of power changes the character. 

It could even be that your powers manifested in a particularly violent way, leaving you on the run and marked as a criminal forever. Perhaps your skills are earned through sheer necessity because you have spent the last few years running from the law. 

Think about and take some time to flesh out your criminal connection. Perhaps they are an unscrupulous halfling that you helped out of a tight spot and so owes you a favor, or someone helped you get out of the clutches of the law after you were captured by a lich to be experimented upon. The possibilities are endless!

Here are some personality traits for your sorcerer:

Warlock Criminal

It doesn’t take much of a stretch to think about how a criminal would make a pact with some great power in exchange for their freedom. Perhaps you were captured for a crime you did not commit or maybe you committed it as part of the pact. Warlocks are opportunists on some level and so that plays into the criminal’s line of work. 

You should consider how your life has changed since making the pact. Did you go from an average peasant to a master criminal on the rise? Did you make the pact to defeat a rival? What do you value more: power or gold? 

Warlocks of any pact can benefit from the skills and contact that you gain from this background so consider how you came about them. You could have been the right-hand man for a crime boss and made the pact so that you can finally dethrone your boss. Or perhaps the skills were gained as part of the pact. In any case, consider the ramifications of the crime and the fall out from you committing it.

Wizard Criminal

A wizard criminal conjures to mind the mad genius or the gentleman thief, a highly educated person who uses their education to exploit the weaknesses of the less brilliant. Your quest for arcane knowledge could be the primary motivation to commit crimes, or perhaps its the other way around and you instead seek to gain larger stores of wealth by perfecting the philosopher’s stone or other magic spells. 

They could be an ex-con who is turning to their magic in order to make some good in a world after their crime damaged it. Your motivation should be rooted in your backstory and can provide the framework with which you make your major character decisions. 

A wizard with the criminal background needs to define who they learned their magic from, how they first became a criminal, and what they plan to do with their magic. They are so capable and brilliant, so why crime? 

Here are some character traits for your wizard:

Next week we will tackle the Entertainer.

Check out past background articles here: Acolyte, Charlatan 

Image from The Complete Thief’s Handbook, a supplement to 2nd edition D&D.