Five new D&D Rogue Subclasses

Introduction

I am very much of the opinion that we should let rogues be rogues. Various third party subclasses make rogues more and more fantastical, magical or merged with celestial or demonic powers that they become quasi spellcasters in their own right. This is ok if you like this sort of thing but it rather drowns out what makes the rogue an interesting character to start with. The first rogues (originally thieves) in D&D were inspired by the Hobbit, where Bilbo Baggins, not a naturally thiefy type at all was recruited by the dwarves because Hobbits can avoid being seen by the big folk when required, and the only person to call Bilbo an actual thief was Gollum, hardly an upstanding judge of public morality.

The thief was a useful character to create for TSR because it enabled players to use dexterity and deception in dungeon crawls and heists, as opposed to magic or raw combat ability. The character class has always been a fan favourite, because basically we all love to be that character that plays fast and loose with the rules and exists partially in the criminal world (something many of us would consider were it not for the legal consequences involved and the amount of time and effort organised crime probably involves).

This article is a way of trying to get back to a simpler, happier time when rogues were rogues. It proposes five subclasses that are involved in the important business of actual crime, not trying to be some sort of superhero with a short sword/

In this article, we'll delve into five unique rogue subclasses inspired by traditional criminal archetypes: the Fence, the Smuggler, the Gangster, the Pickpocket, and the Con Artist. Each of these subclasses brings a distinct flavour to the rogue class, offering new abilities and strategies that can enhance both role-playing and combat.

These subclass ideas might lead to a lower powered campaign, typically a pickpocket character isn't going to be able to be much used against an ancient black dragon. What's the problem with that though? Surely there's a huge amount of roleplaying fun to be had navigating an urban environment as a band of rogues, facing street level threats and anything else sinister that can be encountered in a gigantic metropolis.

The Fence

Concept and Background

The Fence archetype represents the quintessential black market dealer of the criminal underworld. Fences are experts in appraisal, smuggling, and converting stolen goods into gold without leaving a trace. They play a vital role in any criminal network by acting as the bridge between thieves and the legitimate marketplace, ensuring that stolen items are laundered and sold for their true value. A Fence is not just a middleman but a master negotiator with an extensive network of underground contacts, making them indispensable to any heist or smuggling operation. The business of fencing goods involves plenty of role playing, persuasion checks, using contacts to find buyers, being skilled in the art of deception and concealment. When the PCs complete a heist, it's not a done deal until they've collected the gold and covered their tracks. A Fence can be very handy for this.

Abilities and Features

Appraisal Expert: At 3rd level, a Fence gains proficiency in Investigation and Perception. This expertise allows them to assess the value and authenticity of objects quickly. This ability is invaluable during heists when time is of the essence, ensuring that the party only takes the most valuable items. For instance, when exploring a treasure hoard, the Fence can identify which items are worth taking and which are mere trinkets, avoiding unnecessary risks.

Black Market Connections: By 9th level, the Fence has developed an extensive network of contacts within the black market. These connections allow them to obtain rare and illegal items at a 25% discount and sell stolen goods for their full value. This ability can be a game-changer in campaigns where resources are scarce, and acquiring specific items is crucial. Imagine a scenario where the party needs a rare magical component to complete a ritual—through the Fence's connections, they can procure it without breaking the bank.

Hidden Cache: At 13th level, the Fence can create hidden compartments that are undetectable by casual inspection. This ability is perfect for smuggling contraband through heavily guarded areas or hiding valuable items from prying eyes. Whether concealing a stolen artefact within a merchant’s caravan or creating a secret stash in their hideout, the Fence ensures that crucial items remain safe and hidden.

Master Negotiator: At 17th level, the Fence's charisma and cunning reach their peak. They can make a Charisma (Persuasion) check contested by a creature’s Wisdom (Insight) check. On a success, the Fence can manipulate the target into providing information, goods, or favours without realizing they’ve been duped. This ability can be used once per long rest and is particularly effective in high-stakes negotiations or when extracting secrets from wary NPCs.

Role-Playing Tips

A Fence is a specialist rogue, one who clearly knows the value of the stolen goods they are handling. This gives us some clues about their background, how do they know about jewels or other valuable items for example? If they had once been an apprentice to a master craftsman or had been a keeper of the baron's finery perhaps? We're talking about things that require a great deal of knowledge to be able to pass off in a convincing way here. There might be some things that the Fence hasn't got a clue about (nobody is an expert in everything) so being able to use charm an guile to get a good price for it is essential.

When interacting with other characters and NPCs, a Fence should always be looking for opportunities to leverage their connections and skills. They might broker deals between rival factions, secure hard-to-find items for their party, or use their appraisal skills to uncover hidden secrets.

Example Scenario

In the city of Haarkon where crime and commerce intertwine, the party needs to recover a stolen gem from a rival gang. The Fence uses their Appraisal Expert ability to identify the true gem amidst decoys. With their Black Market Connections, they secure information on the gang's hideout and negotiate with a local smuggler for safe passage. As the heist unfolds, the Fence's Hidden Cache ensures the gem remains concealed until the party is ready to sell it, using their Master Negotiator skills to get the best price. This scenario showcases the Fence’s versatility and critical role in orchestrating a successful heist.

The Smuggler

Concept and Background

Star Wars made sure that everyone who has ever want to play a role play game at any point in their lives, secretly wants to be a smuggler. The Smuggler archetype is a rogue who specializes in covert transportation and navigating treacherous routes. These rogues are masters of moving contraband and valuable items through dangerous and heavily guarded areas without detection. Whether by land or sea, a Smuggler’s expertise in evasion and route planning makes them indispensable for any party needing to transport goods discreetly. With their extensive knowledge of hidden paths and secret compartments, they ensure that their cargo arrives safely and undetected. There are more opportunities to be a 'white hat' rogue here, perhaps the PC is smuggling weapons or secret intelligence to an oppressed people, or they are trying to outrun a blockade to city under siege. Smuggling contraband also forces to ask 'what is banned and why?' This can present the DM with some really exciting world building opportunities.

Abilities and Features

Hidden Compartments: At 3rd level, a Smuggler gains proficiency with vehicles (land and water) and can create hidden compartments in these vehicles or their clothing. Mechanically, these compartments are nearly undetectable, requiring a high DC Investigation check to be found. Narratively, this ability allows the Smuggler to conceal weapons, contraband, or important documents within seemingly innocent items or parts of a vehicle. For example, a hidden compartment in a wagon might store stolen jewels or a secret map, allowing the Smuggler to pass through checkpoints without raising suspicion.

Route Master: By 9th level, the Smuggler has become adept at navigating the safest and most efficient routes through both urban and wilderness environments. This mastery grants advantage on Survival and Stealth checks related to travel. In game terms, this means the Smuggler can lead their party through perilous terrain while avoiding natural hazards and enemy patrols. Whether escaping through a dense forest or navigating a labyrinthine city, the Route Master ability ensures the party moves swiftly and undetected.

Evasion Expert: At 13th level, the Smuggler’s reflexes and agility are unparalleled. They gain the ability to use the Dodge action as a bonus action, giving them a significant edge in combat by making them harder to hit. Additionally, they can automatically succeed on one Dexterity saving throw per short or long rest. This combination of abilities makes the Smuggler extremely difficult to pin down in a fight, allowing them to evade traps, spells, and attacks with ease.

Ghost in the Night: At 17th level, the Smuggler attains near-mythical levels of stealth. They can become undetectable by magical means for up to 1 hour once per long rest. This means spells like detect magic and scrying cannot locate them, and they leave no trace of their passage. This ability is invaluable for high-stakes missions where absolute secrecy is required. For instance, smuggling a magical artefact out of a heavily guarded fortress becomes feasible when the Smuggler and their party can move without leaving any magical signature.

Role-Playing Tips

Creating a compelling Smuggler character involves weaving a backstory filled with perilous journeys and close escapes. Perhaps your Smuggler grew up in a port city, learning the tricks of the trade from seasoned sailors, or they might be a former noble who turned to smuggling to fund a rebellion. Like Han Solo, they might have run into trouble in the past and dumped their cargo, much to the annoyance of powerful underworld figures.

In-game, the Smuggler should always be on the lookout for the safest routes and the best ways to avoid detection. They might scout ahead to find hidden paths, negotiate with informants for crucial information, or use their hidden compartments to protect the party’s valuables.

Example Scenario

In a bustling port city of Tokairo, now under strict martial law from the city's despotic duke, the party needs to transport a cache of stolen weapons to a rebel group. The Smuggler uses their Hidden Compartments ability to conceal the weapons within innocent-looking cargo. With their Route Master skills, they navigate the safest backstreets and waterways, avoiding patrols. As they encounter unexpected checkpoints, the Smuggler’s Evasion Expert ability ensures they slip through undetected. Finally, as they approach the rebel hideout, the Smuggler activates Ghost in the Night, ensuring the final leg of their journey remains invisible to magical surveillance. This scenario highlights the Smuggler’s critical role in ensuring the success of the mission.

The Gangster

Concept and Background

If you're going to play a criminal, play a proper criminal. Play a crime boss, someone who takes care of business; there's a lot more to criminality than just stealing things. The gangster controls city territory, makes sure that nothing happens on their turf without their knowledge and deals with rivals forcefully. They know that the streets are a hard, unforgiving place where hesitation and weakness mean death. The gangster isn't all bad though, there are plenty of people that depend on them who they protect. Any gangster rogue offers ideal roleplaying opportunities because this is a conflicted character, someone who lives by harsh and uncompromising rules, but also tempers that with a bit of honour. They never snitch, they never forget a debt (or an enemy) and they are loyal to their gang. These rogues are street-savvy enforcers and masterminds, building criminal enterprises from the ground up. A Gangster thrives in urban environments, where they can establish protection rackets, control territories, and lead a network of informants and underlings. They are not just thugs; they are strategic leaders who know how to manipulate the criminal underworld to their advantage.

Abilities and Features

Intimidating Presence: At 3rd level, a Gangster gains proficiency in Intimidation, allowing them to leverage their fearsome reputation. As an action, they can attempt to frighten a creature within 30 feet. The target must succeed on a Wisdom saving throw (DC equal to 8 + your proficiency bonus + your Charisma modifier) or be frightened of you for 1 minute. This ability can be used a number of times equal to your Charisma modifier (minimum of once) per long rest. Mechanically, this provides a strategic advantage in combat by causing enemies to flee or become incapacitated with fear, creating openings for the Gangster and their allies to strike.

Criminal Network: By 9th level, the Gangster has cultivated a network of informants and underlings who provide valuable information and resources. This network grants advantage on checks to gather information in urban areas and can be called upon to secure temporary resources or muscle. In-game, this means the Gangster can quickly learn about upcoming threats, potential heists, or the movements of rival gangs, giving them a strategic edge.

Protection Racket: At 13th level, the Gangster can establish a protection racket, demanding tribute from businesses and individuals within their territory. As an action, the Gangster can demand tribute from a creature within 30 feet. The target must succeed on a Wisdom saving throw (DC equal to 8 + your proficiency bonus + your Charisma modifier) or be charmed by you for 1 hour. During this time, they will do their best to fulfill your demands, providing money, information, or other resources. This ability can be used once per short or long rest. Strategically, this ability allows the Gangster to extract resources without direct confrontation, consolidating their power and influence.

Kingpin: At 17th level, the Gangster’s control over the criminal underworld is unparalleled. They can command their network to perform major tasks, such as orchestrating a heist, assassinating a target, or providing a safe house. This ability can be used once per long rest and requires at least 1 hour of planning. The significance of this ability lies in its capacity to shape the narrative of a campaign, enabling the Gangster to execute complex and high-stakes operations with the backing of their criminal empire.

Role-Playing Tips

Can you have a nice gangster? Probably not, these characters have to thrive on an air of menace, even if they have those they love and protect. Creating a compelling Gangster character involves crafting a backstory rooted in the gritty realities of urban life. Perhaps your Gangster rose from the slums through sheer force of will, or they might be a fallen noble seeking to regain power through criminal means. The streets are the gangster's teacher, learning some hard rules about power and how it is harnessed. In-game, the Gangster should focus on establishing and expanding their influence. This could involve intimidating rivals, negotiating with other criminal elements, and using their network to stay one step ahead of the law. Interactions with other characters should reflect their ruthless and strategic nature, always looking for ways to turn situations to their advantage.

Example Scenario

In the desert city of Rios, a metropolis rife with gang warfare, the party needs to broker peace between rival factions to prevent an all-out war. The Gangster uses their Intimidating Presence to command respect during negotiations. Leveraging their Criminal Network, they gather intelligence on the factions’ weaknesses and strengths. By establishing a Protection Racket, they secure vital resources and sway key figures. Finally, as tensions rise, the Gangster’s Kingpin ability orchestrates a decisive operation that forces the factions to the bargaining table, showcasing the Gangster’s critical role in achieving peace through strength and strategy.

The Pickpocket

Concept and Background

The Pickpocket archetype is a rogue who excels in sleight of hand and deception, making them masters of subtlety and misdirection. These rogues are adept at lifting purses, planting items, and manipulating small objects with unparalleled dexterity. In a world of intricate plots and hidden treasures, a Pickpocket thrives by remaining unnoticed and striking when least expected. Whether working alone or as part of a crew, their skills make them invaluable for missions requiring stealth and finesse.

Abilities and Features

Sleight of Hand: At 3rd level, a Pickpocket gains proficiency in Sleight of Hand and Deception, if they do not already have it. This ability allows them to manipulate objects and lift items without detection. Mechanically, this provides advantage on checks to pickpocket, plant items, and perform delicate tasks. Narratively, a Pickpocket might steal a key from a guard’s belt without being seen or plant incriminating evidence on a rival. The ability to manipulate small objects also comes in handy for disarming traps and unlocking doors with finesse.

Quick Fingers: By 9th level, a Pickpocket's agility and dexterity allow them to use the Use an Object action as a bonus action. This enhances gameplay by providing more options during combat and exploration. For example, a Pickpocket can quickly apply poison to a weapon, throw a flask of alchemist’s fire, or pull a lever while still having their action available for other tasks. This versatility makes them extremely efficient in dynamic situations where every second counts.

Master of Disguise: At 13th level, the Pickpocket can use the Disguise Self spell at will without expending a spell slot. This ability provides tactical advantages in numerous scenarios, allowing the rogue to change their appearance on the fly to blend into different environments or avoid detection. Whether infiltrating a noble’s masquerade ball or evading capture by assuming the guise of a city guard, the Master of Disguise ability ensures that the Pickpocket can navigate social and hostile situations with ease.

Grand Larceny: At 17th level, the Pickpocket attains the ability to steal objects with a single touch. When they hit a creature with a melee attack, they can use their bonus action to make a Sleight of Hand check contested by the target’s Dexterity (Acrobatics) or Wisdom (Perception) check. On a success, they steal one object the target is carrying that is not worn or wielded. This ability can be used once per short or long rest. The significance of Grand Larceny lies in its potential for high-stakes thefts, such as stealing a powerful magical artefact from an enemy in the midst of battle.

Role-Playing Tips

Developing a compelling Pickpocket character involves crafting a backstory filled with close encounters and daring heists. Your Pickpocket might be an orphan who survived on the streets by stealing, or a disgraced noble using their skills to uncover secrets and seek revenge.

In-game, focus on effective stealth and subtlety in interactions. Use your sleight of hand to manipulate events behind the scenes, create diversions, and gather crucial information. Build relationships with NPCs who can provide cover or look the other way during your exploits.

If you ever find yourself thinking that sleight of hand isn't a powerful ability, remember that it was only this that saved the entire universe at the end of the day in Avengers Endgame.

Example Scenario

In a heavily guarded fortress city of Khoese, the party needs to steal a valuable amulet from a high-security vault. The Pickpocket uses their Master of Disguise ability to infiltrate the premises by posing as a servant. Once inside, they employ Sleight of Hand to bypass traps and security measures. During a critical moment, Quick Fingers allows them to disable an alarm while still having the ability to react to threats. Finally, with Grand Larceny, the Pickpocket steals the amulet from the vault, ensuring the party’s mission is a success without raising any alarms. This scenario highlights the Pickpocket’s essential role in executing delicate and high-risk operations.

The Con Artist

Concept and Background

The Con Artist archetype represents a rogue who excels in deception, manipulation, and running elaborate scams. These rogues are masters of charm and wit, able to weave intricate lies and schemes to achieve their goals. A Con Artist can manipulate almost anyone, from commoners to nobles, making them invaluable in scenarios where cunning and charisma are more effective than brute force. Whether posing as a wealthy merchant or a trusted advisor, the Con Artist uses their skills to turn situations to their advantage, ensuring they always come out on top. Role playing a con artist might not be as easy as it seems, the player actually has to put a lot of work beyond the dice rolls into being plausible, believable and charming (DMs, don't give a free pass to Con Artists who don't even try to be convincing).

Abilities and Features

Silver Tongue: At 3rd level, a Con Artist gains proficiency in Persuasion and Deception, if they do not already have it. Additionally, they can use their action to gain advantage on a Charisma check to deceive, persuade, or bluff. This ability allows the Con Artist to manipulate conversations and negotiations, turning the tide in their favor. For example, they might convince a guard to let them pass without proper identification or persuade a merchant to offer a significant discount on crucial supplies.

False Identity: By 9th level, the Con Artist has mastered the art of maintaining a false identity. They can create and sustain a believable persona, complete with forged documents, signatures, and backstories. Mechanically, this grants advantage on checks to maintain the false identity and forge documents. Narratively, this ability allows the Con Artist to infiltrate organizations, gain the trust of key figures, and access restricted areas without arousing suspicion.

Master Manipulator: At 13th level, the Con Artist can cast *Suggestion* once per short or long rest without expending a spell slot. This ability provides strategic benefits by allowing the rogue to subtly influence the actions of others. Additionally, they have advantage on checks to persuade or deceive creatures under the effect of their *Suggestion*. This can be used to turn enemies into temporary allies, secure information, or manipulate events to the party’s advantage.

The Long Con: At 17th level, the Con Artist can orchestrate a complex and multi-part scheme. By spending 1 hour planning, they can grant themselves and up to six allies advantage on all checks related to the con for the next 24 hours. This ability is significant because it allows the Con Artist to execute elaborate plans involving multiple steps and participants, such as infiltrating a heavily guarded estate or swindling a powerful noble out of valuable resources.

Role-Playing Tips

Creating a compelling Con Artist character involves crafting a backstory filled with cunning schemes and narrow escapes. Your Con Artist must be an excellent actor and be able to believe their own performance. The Con Artist might have been a street urchin who survived by their wits, or a disgraced noble using their skills to regain power and wealth. In-game, focus on running cons and scams effectively, always have some sort of scheme running, use the arts of persuasion, using the greed and fear of others to your advantage. Develop detailed plans, create believable personas, and use your Silver Tongue to manipulate conversations. Interact with NPCs strategically, always looking for ways to turn situations to your advantage and achieve your goals through deception.

Example Scenario

In a campaign scenario where the party needs to gain access to Baron Megrande's heavily guarded estate, the Con Artist uses their False Identity to pose as a wealthy merchant. Leveraging their Silver Tongue, they convince the guards of their authenticity and gain entry. Inside, they cast Suggestion on key servants to extract vital information and navigate the estate without raising suspicion. Finally, with the advantage from The Long Con, the party executes a flawless heist, showcasing the Con Artist’s critical role in orchestrating complex schemes.

Conclusion

The five unique rogue subclasses—the Fence, the Smuggler, the Gangster, the Pickpocket, and the Con Artist—each bring their own flavor and strategic depth to the rogue class. By tailoring their abilities to specific criminal archetypes, these subclasses offer players diverse and exciting ways to engage with their characters and the world around them. From the Fence's mastery of appraisal and black market dealings to the Con Artist's intricate scams and manipulations, these archetypes enhance both gameplay and storytelling.

These subclasses not only expand the tactical options available to players but also provide rich opportunities for role-playing and character development. Whether you’re leading a criminal empire, smuggling contraband through dangerous territories, or executing high-stakes heists, these rogue archetypes will bring a new level of excitement and depth to your Dungeons & Dragons campaigns.

Appendix: Additional Resources

Suggested Reading:

- The Complete Thief's Handbook (from back in the day...) by Robin D. Laws for advanced rogue tactics and role-playing tips.

- Waterdeep: Dragon Heist by Wizards of the Coast for inspiration on urban adventures and criminal intrigue.

- The Lies of Locke Lamora by Scott Lynch for a novel filled with cunning heists and complex cons that can inspire rogue characters and plots.

Online Resources:

D&D Beyond for official D&D resources, character builders, and community forums.

Critical Role for episodes featuring diverse and dynamic rogue characters.

Reddit's D&D Community for discussions, advice, and homebrew content from other players and DMs.

Tools and Supplements:

Roll20 for online tabletop gaming and campaign management.

Hero Forge for customizable miniatures to represent your rogue characters.

The Enter The Arcverse Store for one shots, core books, maps and more