Rogue Bounty Hunt

Criminal Rogue Professions in D&D 5e

Rogue profession as criminals in D&D 5e featured image is “Bounty hunter” by Feael, CC Attribution-Noncommercial-No Derivative Works 3.0 License
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Villainy is underestimated as a tool for benevolence in Dungeons and Dragons. Sly underworld skills can change the tide of a campaign in favor of the good guys. These skills are not monopolized by Rogues. They naturally excel at clever capers as benevolent criminals, deploying dastardly tactics to get things done.

Let’s explore unwholesome tricks adventuring parties can use to achieve righteous their goals.

Rogue Professions and Schemes for Parties

We’ve probably all played a game where a Rogue goes off on her own for an hour. The rest of the table has to watch and wait; it’s not so fun. I’ll provide tips for Rogues to include entire adventuring parties in their schemes. Doing so brings more fun to the table. 

Don’t forget that you don’t have to play a Rogue to apply these ideas. Anyone can be a benevolent criminal with proper planning!

Blackmailer – Rogue Profession

A Blackmailer needs to have the upper hand on others in order to enact their worthy deeds. Gain information about people creatively, ideally without their knowledge, and blackmail them in secrecy. The less they know about who is blackmailing them, the better, as they cannot take countermeasures to nullify your knowledge.

You can infiltrate cults to gain blackmailable details about high-level officials. Working for powerful members of society gains you access to their documents and valuables. Cover-ups become clear to you as you assist people in their less-than-legal dealings and keep evidence of the event.

Another method is to blackmail a low-level, yet vital member, of an organization. Most people are working for a living and don’t have a deep loyalty to an employer. If something doesn’t affect them, or so they are led to believe, they’ll comply. A guard that can let you through a door without incident is a prime target. Keep your mole quiet with fear of losing their job. That fear outweighs loyalty to an organization. The actual targets will be baffled as to how things happened.

Parties: Play the fool and befriend those you are trying to blackmail. Act as a double agent and let your Rogue do the actual blackmailing. 

Burglar – Rogue Profession

More than just pickpocketing, burglary involves high-stakes planned operations. They achieve a specific purposes, whether that be monetary gain, acquiring a specific item of value, or stealing important documents. Burglary requires diverse honed skills:

  • Silently parkouring through narrow windows.
  • Deploying compact tools to remove window bars from fourth-story buildings.
  • Keeping tabs on each watchman in a building. 

Powerful people will often have traps and arcane wards to protect their inner sanctums. Burglars must deal with environments that are likely tailored to hide the most valuable items. Those environments will likely punish anyone that discovers them.

A burglar can infiltrate areas that are assumed to be safe and defensible. If your party has a burglar, that burglar can fill a myriad of roles mentioned in this article. Focus on the Thief archetype for skills like quick climbing and supreme sneak.

Parties: A lot of work is required prior to the burglary. Burglars gather information, identify means of access, infiltrate inner circles, etc. Think of the Oceans movies and how much preparation goes into those heists. Choose a role, from handling logistics to being the inside man to volunteering to be getaway drivers.

Enforcer – Rogue Profession

A criminal organization is only as good as its ability to enforce its rules, so it needs an enforcer: someone to track down squealers and shake down the in-debted. This role is traditionally carried about by muscle-bound brutes, but Rogues can do the job just as well. In fact, Rogues can have high Strength stats if they really want to.

Rogue players can become the muscle behind any particular organization as a way to enact personal justice by releasing squealers into the wind while lying for them and paying off a peasant’s debts. They may lie and say they coughed up the payment. This is also a great way to gain the trust of an organization and learn its secrets—such an organization need not be openly evil but could instead be a government function such as tax collection.

Parties: An enforcer is more intimidating with a posse backing them. Designate someone to do the talking (preferably with high Charisma), and the others can be ready for a fight. Spellcasters can be especially helpful for getting things done without bloodshed, such as by casting Levitate to lift some poor sap and shake the gold from his pockets.

Fence (Black Market Middleman) – Rogue Profession

Normal merchants won’t buy stolen goods, so they need a middleman between them and the Black Market. A good Fence will be discreet, observative, trustworthy, and well-connected to the criminal world. Perhaps a former-criminal-turned-adventurer can utilize old contacts; maybe a Rogue has a Smuggler background; perchance, a character is well-known in the fine arts industry, providing the perfect cover.

How could a party benefit from this position? A sneaky Fence could be a valuable double agent. Be aware of what comes in and out of the city; thwart bad parties from smuggling in dangerous items; steal items that would be necessary for your adventure. These things should be handled gently, as a Rogue would lose his position as a Fence if someone found out he was to blame.

The Thief archetype can be useful, with abilities like Fast Hands, Supreme Sneak, Use Magic Device, and Thief’s Reflexes. Choose a background that can provide proficiency in vehicles to transport and hide your goods.

Parties: During trades, Fences will need bodyguards. Help your Rogue keep a low profile by being discreet as well. Perhaps a party member has vehicle proficiencies the Rogue can rely on.

Forger – Rogue Profession

Forging is a tricky skill that often goes unutilized in a game, but it can have immense world-affecting benefits.

Forge a suicide note and last will; fabricate a diary that discusses a secret lover; create a land deed; write a certificate ensuring the authenticity of diamonds, and bestow them upon a foe who wishes to use them for the Resurrection spell, or develop certificates of authenticity for fake ritual items like a dragon’s egg or a holy relic.

By providing fake items to evil wizards (perhaps with the Fabricate spell), you can cast a Locate Object spell to track down the item, spy on the perpetrator, and catch them in their dastardly deeds without the risk of them actually being able to use the item in their rituals.

Parties: You can convince a buyer to purchase a falsified item by acting interested in the goods. You can also be a witness to documents being created authentically if their legitimacy is questioned. And finally, you can also use your expertise in acquiring fake items with your knowledge of arcana, history, and persuasion.

Framer – Rogue Profession

Sometimes tied to thievery, a framer can easily sick lawmen on a victim. With skills in forging and disguising, a Rogue can either enact evil deeds herself disguised as another person, or she can fabricate evidence that incriminates a foe. 

A person interested in framing should focus on deception, performance, sleight of hand, persuasion, and stealth. An Arcane Trickster could choose spells like Disguise Self, Illusory Script, Major Image, Fabricate, and other spells that distort the perception of events. 

Parties: Integrate into a crowd and start rumblings about someone being guilty. Cry “He stole my purse!” or whisper, “that man is a murderer!” to help the Framer’s plot play out.

Haggler – Rogue Specialty

What’s the true price of an item if not the value the buyer grants? Whether selling for an enormous profit or buying at a bargain, a haggler may be necessary for obtaining material components, tradable goods, or particular pieces that would seal a life-or-death deal. 

Focus on skills of persuasion, history, and archetypes or backgrounds that bring social influence and popularity. You can trade favors for bargains, deploy bribery, and employ sob stories with good performance.

Parties: Egg on buyers and sellers subtly through the art of manipulation. Charm or intimidate individuals, and use your history and investigation skills to find worthwhile goods.

Highwayman – Rogue Gangs

The dangerous craft of highway robbery is perfect for brazen adventuring parties, especially if they discover routes of crooked merchants or corrupt governments. This type of operation is ephemeral, possessing high stakes. I guarantee a party of players will put heaps of planning into this kind of operation, and they’ll be either jubilant or depressed afterward (depending on the results).

Rogues of the Scout archetype may be particularly adept in highway robbery, not slightly owed to their skills with survival and nature. Highway robbery relies heavily on location, so make sure to pick a spot that gives cover, prevents escape, and avoids nearby settlements and patrols.

Parties: Create a roadblock or waylay a caravan long enough to either intimidate or fight foes for their goods. Alternatively, a stealthy PC can take advantage of the commotion to sneak in and snatch a specific item or person. This is also where it helps to have a Rogue that is both strong and dexterous, especially if nabbing a person. One party member may even act as someone in need on the road as they feign to be passed out on the path. Wizards may cause a layer of fog to roll in over a caravan at an opportune moment for the party to make a move.

Launderer – Rogue Professions

Currency functions differently in fantasy games than in real life, in that your characters would have physical coins worth their weight in gold. Counterfeiting money can be difficult or costly. But, obtaining ill-gotten currency may require laundering, especially if different kingdoms have unique mintage, as this may make identification of criminal activity easier. Smelting down the gold and reforming it into new coins with common mints is one method, which would require skills in smithing and perhaps forgery. 

A player who has access to these services can provide an interesting proposition to underground criminal organizations. Curry favor with warlords; trade your services for mercenaries’ protection; trade a ceasefire for monetary gain. After all, money moves mountains. 

Parties: If you have skills in smithing or crafting, or if you have magical means to transmute materials, such as with the Fabricate spell, you can be a valuable asset. Furthermore, a player with high Charisma may be needed in forming these deals with hardened criminals.

Liar – Rogue Specialty

Rogues are not typically known for high Charisma, but they can choose skills that assist in verbal skullduggery. With Deception, Performance, and sometimes Intimidation, a Rogue can spread gossip and rumors that sow the seeds of manipulation.

Consider acquiring the Diplomat feat, which increases your Charisma, gives proficiency in Persuasion, and allows you to verbally charm a person.

Parties: Use your magic and skills like Charm Person, Friends, Suggestion, or College of Whispers (Xanathar’s Guide to Everything) features to assist a Rogue in his plans.

Kidnapper – Rogue Profession

I really don’t recommend stealing away children (what are you, a hag?), but I do recommend a tactical person heist. If the villain’s wife goes missing by your hand, you can maneuver the villain into a situation more advantageous to your party. Kidnap a corrupt official’s child to tenure his resignation. Stow away some high-ranking individuals to get law enforcement to start an investigation that would reveal a greater conspiracy. Additionally, instead of slaying your enemy in Mortal Kombat, you can demand a ransom to stick it to his wallet instead.

Parties: You can help care for kidnapped individuals with your Medicine and Nature skills to ensure nothing goes wrong. You may also be invaluable in the kidnapping process, providing spells like Pass Without Trace and Levitate.

Killer – Rogue Profession

Assassination is a very lucrative occupation. Moreso, knowing who has a bounty on their head is worth the weight of the world in gold. Recognizing the calling cards and methods of the top assassins can help a party thwart murderous attempts or provide invaluable information to law enforcement.

As a vigilante, a Rogue and party can take justice into their own hands during the reign of a corrupt regime. End war lords’ terror by removing his top generals; force re-election of better politicians by terminating crooked officials; circumvent an assassination attempt by slaying a rival assassin.

Parties: There are a lot of gray areas when it comes to vigilante killings. You may have to decide for yourself how to be involved or not be involved at all. Consult your gods, assess your character’s motivations, and perhaps think of solutions you can try with killing as a last resort.

Pickpocket – Rogue Specialty

Don’t think small as a pickpocket. Pickpocketing is especially underappreciated as a tool in combat. The average roguish player wants to steal for the purposes of getting rich or being chaotic, but thievery can be used for so much more.

You can steal valuable combat items right before the fight begins, potentially leaving an enemy dead in the water. Spellcasters need arcane focuses and expensive components; martial classes need weapons and ammunition; a wizard requires his spellbook to function. If you can covertly remove said items from your enemies before a fight, they’ll be grappling with the surprise of their gear being gone. You might even leave decoy items in their places, such as a banana instead of a dagger or a bag of sneezing dust instead of a bag of ruby dust for casting Forcecage.

Stealing a coin purse comes naturally to a Rogue, but timing can make it better. If you know a corrupt merchant is on her way to making a massive purchase, that’s the time to strike. When you time your thievery this way, you enjoy the satisfaction of watching the mercantile dominos fall while you count your hard-earned coin.

Parties: Distractions are helpful for succeeding in a pickpocket operation. Party members can create social distractions or cause commotions to provide an opportunity for a Rogue to pickpocket a target (probably with advantage).

Saboteur – Rogue Profession

Along those same lines of pickpocketing to thwart battle, a player who engages in sabotage can be a valuable asset. Jam a door to prevent escape from a fight or a poison gas attack; remove a component of a machine; sneakily secure a rope to a problem person’s leg, then drag the victim behind a horse carriage. The art of sabotage is vast and creative. 

Additionally, a Rogue can specialize in being a Mastermind (Sword Coast Adventurer’s Guide) and use “Master of Intrigue” to mimic the speech and accent of a creature they observe. Sabotage noblemen’s plans by disguising as them; incite a riot by blending in with the locals, or feign to be a prince and woo a princess to convince her to stop the villain’s plans. Arcane Tricksters (Player’s Handbook) can use illusion magic to achieve similar trickery.

Parties: Rogues should rely on other members of the party for their useful skills, like tinkering or magical efforts that would sabotage machines. Other characters, high in Charisma, can be employed to convince people to do something that would thwart plans.

Smuggler – Rogue Profession

Many backgrounds, such as the sailor and soldier, provide proficiency in land and water vehicles. You might as well put those skills to use. If you meet someone powerful, you can gently suggest that you have ways of getting hidden items and people past watchful borders. This may seem like one of the least common skills to apply in this article, but a reflection on real-world smuggling and trafficking quickly brings ideas to mind.

It may be that there is political unrest about particular groups of people, contraband goods, or tariffed trade that you can get around. This is a great way to curry favor with powerful people if you’re willing to take on the risk. 

If you’re not keen on helping others, you can run your own operations based on your moral compass. Perhaps you run some kind of underground railroad to free slaves, or you smuggle medicine into an area that bans it for political/religious reasons. Perhaps you can smuggle a snitch out of a city after she testifies against the king, securing her testimony by offering safety.

Parties: This kind of operation can’t be just one person’s undertaking. The party will need support as ship or caravan crewmen while keeping things quiet. Enchanter Wizards can be of particular use when getting border guards to look the other way, but anyone with some coin and a silver tongue can do the trick.

Spy – Rogue Profession

Similar to a Blackmailer, information is king for a spy. You wield power over people if you always know where they are, what skills they have, what their moral vices are, where their loved ones live, where they store their money, and anything else about them. 

Additionally, spies rely on networks to pass information around. Focus on the criminal background to get in with the underground spy circles. The Charlatan background is also helpful for Deception, Sleight of Hand, and the Disguise and Forgery Kit proficiencies.

Be creative in methods for gaining information about a person. Plant a tracking device if you have the Locate Object spell; infiltrate cults in disguise to learn blackmailable details about high-level officials; seduce or work for powerful members of society to have access to their private documents.

Parties: Use your background and skills to gain information. Assist with spells that read thoughts, charm people, disguise a person, or compel the truth. Use your familiars or homunculi to spy as well.

Trap-Setter – Rogue Specialty

Consider a Rogue’s adeptness at setting mechanical traps. In Xanathar’s Guide to Everything (pg. 84), the Thieves’ Tool is revisited and clarified to be useful in setting traps.  

“Set a Trap. Just as you can disable traps, you can also set them. As part of a short rest, you can create a trap using items you have on hand. The total of your check becomes the DC for someone else’s attempt to discover or disable the trap. The trap deals damage appropriate to the materials used in crafting it (such as poison or a weapon) or damage equal to half the total of your check, whichever the DM deems appropriate.”

A sneaky Rogue could employ this before a battle or during all of the commotion. For example, consider pushing boulders down cliffs onto your foes, dropping spiky caltrops on a grassy area during a chase, or restraining your enemies by throwing nets.

Parties: Distraction may once again be key here. If your Rogue is setting up a trap, keep your enemy focused on you. You may need to buy time with an epic in-game monologue.

You Should Embrace Criminality as a Rogue!

For good or for evil, Rogues have a myriad of valuable albeit mischievous abilities ingrained into their character build. Impressively, a Rogue may use her wicked methods to do good in the world. Find ways to fake out foes, sabotage the sadistic, and acquire items necessary to save the world.

For additional guidance on building your Rogue, consider reading our Rogue-Fighter Multiclass Guide.

You can also find ideas to re-flavor your Rogue from the Cleric Corner.

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