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OSR: Scoundrel

  • seeroftheabyss
  • Jul 5, 2025
  • 17 min read

Updated: Jul 21, 2025

You are a member of the underclass, or at least affiliated with the dark and seedy parts of the world. Work with your Referee to make a place for your character, or roll on the tables below:


When was your first brush with crime?


1d3

1- I was born to it. Your mother, father or both parents were involved in the underworld from the moment you were born. You were born in a bad neighborhood and nutured on crime and deceit, it was your swaddling clothes and mother's milk. You likely have a very warped moral compass and massive daddy issues.

2- When I was a child. You suffered a tragedy when young and ended up having to survive on the streets, or were inducted into a gang when you were young. You're a hard-bitten, scrappy survivor.

3- Recently, you suffered a sudden brush with the underworld, either because you plunged into it or because you were victimized.


Who was your Mentor?


1d6

1- A charismatic con artist. They seem to like you, but how much can you really trust them?

2- An older man or woman you are hopelessly smitten with. They might know and be leading you on, or they might simply not notice your feelings.

3- A kinsmen of yours. Your brother, uncle, cousin or other family member who got into this before you, and now they're pulling you down that same path.

4- A local crime boss. You work for the boss because 1d4 [1= You're related. It's the family business; 2= You owe him an enormous amount of money and need to pay him back, if you don't want to have a very bloody accident; 3= He is black-mailing you using a secret from your past that you thought buried; 4= The boss helped you when no one else would.]

5- A fellow outcast. You never quite fit in, and neither did he. As such, he has taken you under his wing, to try and protect you, to show you what it took him many painful years to learn.

6- A kindred spirit. Something about you strikes a cord with your Mentor, who sees a younger version of himself in you. He feels a unique connection to you and wants to guide and shape you into something better than what he is.


What do you owe them?


1d4

1- Everything. Your Mentor saved your life, literally or metaphorically. When the world crashed down on you, they dug you out and helped you get back on your feet.

2- A great debt. Your Mentor did you a great service and you feel pressured to do something to pay them back.

3- A fresh start. You promised you would help your Mentor start over, start fresh, but only once he's had his fill.

4- Nothing, but you don't feel that way. Your Mentor made it very clear that he helped you on a whim because he chose to, and not because he wants anything from you. But even so, you still likely feel inclined to help him.


What can your Mentor do for you?


1d8

1- He's an excellent safe-cracker and is good at disabling traps and other security devices.

2- He is strong and works as muscle for a gang, or he knows someone who is.

3- He's silver-tongued, able to get information out of people, or she's a femme fatale able to seduce her way to any secret.

4- He's a semi-famous and highly skilled highwayman or other form of robber.

5- He's an excellent burglar, able to easily break into most places and escape without being seen.

6- He's an assassin, a highly proficient one.

7- He's a smuggler, able to sneak in illegal goods and smuggle out other sensitive cargo.

8- He's an information broker and a whisper-monger, with ears everywhere. His sources are very reliable and he'll share what they say, for a price.


What are you after?


1d4

1- Money. Maybe you want the money because it's the only way the girl you love will ever notice you, or maybe you feel it's the only thing that can protect you, or maybe you're just greedy.

2- You want to be famous. One day, people are going to tell stories about how smart, how cunning and how awesome you were. You're going to carve your name into history.

3- You want to show them all. Those people who rejected you, who laughed at you, who tormented you, you'll prove that they were just a bunch of phonies and failures, you'll become greater than they ever were.

4- Daddy's love. You want to make your Father (or Father figure) love you, as he's regarded you as a failure your whole life.

from here
from here

Scoundrel

Starting HP: 1/3 Con

Fighting Spirit: +1 per Scoundrel level, up to COG score

Atk Modifier: +1 per Scoundrel level (max +7)

Starting Equipment: Knife, clothing appropriate to your level and station, a foppish, extravagent outfit or fake creditentials, loaded dice or thieves' tools, home-made map covered in shorthand only you and select others can understand


Abilities:

1: Criminal Encyclopedia, Sense Motive, Trick of the Trade

2: Dirty Fighter, Criminal Competence

3: Fast Hands

4: Sneak Attack

5: Great Escape

6: Fog of War

7: Master of Disguise

8: Danger Sense

9: One Last Job


1:


Criminal Encyclopedia: You grew up around crime and criminal activity, and thus know it pretty well. You automatically know anything someone raised in a rough neighborhood would know, such as local gangs and rackets, crime bosses, how to steal a coin-purse without getting stabbed, etc. Most of this knowledge is automatic, so if the Thief is about to do something dumb, you (the Referee) should tell them about the mistake they're about to make. Additionally, unless failing to know something might have dramatic consequences or there's no way the Scoundrel could know, answer any questions the Scoundrel might have on criminality. If in doubt though, the Referee should call for a check.


Sense Motive: When in conversation with someone, you can make a check to determine someone's motivation while talking to them. Creatures can try to resist you if they're trying to deceive or conceal their true intentions, but unless they're trying to do that, they likely will not. However, just because someone's being honest doesn't mean you can understand them. Potential motivations can include, but are not limited to, things like "Honor", "Greed", "Pride" or "Fear".


Trick of the Trade: You start with one of the 'Tricks of the Trade'. You can roll randomly or select one. For each 2 Rogue levels after this, you can pick another or roll again on the table. If you roll a result again, you gain a deeper knowledge of the subject. If you wish to pick a result, you cannot pick the same option twice. You gain another Trick at 3rd, 5th, 7th level and 9th level.


2:


Dirty Fighter: If you use a dishonorable tactic or a dirty trick against an opponent, you gain advantage on your next attack against that specific creature and that creature gains disadvantage on it's next attack. A dirty tactic is anything that would be considered not within the bounds of fair play, such as throwing sand in an opponent's face, tackling someone and covering his face with a bag, dropping a chandelier on his head, etc. Referee's Discretion applies on whether something counts as a "dishonorable tactic or dirty trick".


Criminal Competence: Pick one of the following skills. You gain a +1 to any roll based on that skill. You may select another skill at Level 4, 6 and 8 or increase your bonus to one skill by +1. These skills are:

- Moving silently

- Climbing

- Lock-Picking

- Finding Traps

- Forging Documents

- Pick-pocketing

- Wearing disguises


3:


Fast Hands: When you attack an enemy and successfully hit them, you can, instead of dealing damage, do something else to them, such as pick-pocket them, cut their sword-belt so they drop their sword, or plant something on them. However, this does not work on something someone is actively protecting. For example, if they are currently tightly holding onto something, Fast Hands could not take it from them. But if it was hanging from their belt, it could. When in doubt, the enemy gets a saving throw. On a success, the Thief cannot do what they asked.


4:


Sneak Attack: When attacking an enemy that cannot see or detect you, or is otherwise not expecting you to attack them, you have advantage on your attack roll. Additionally, you may roll your damage di(c)e twice and select the better result.


5:


Great Escape: You are slippery like an eel. If you can think of no way out of situation, no clever way to escape the clutches of a foe, 1/Day your criminal mind can suddenly reveal an escape route. The Referee should immediately point out a weak-point in the enemy's defenses, a potential chink in the armor, or some other vulnerability you overlooked.


Note to the Referee: This is not where you just let the players go. All you should do is tell the players about a weak point and give them an escape route.


6:


Fog of War: When in combat or in a chaotic situation, such as an evacuation, a housefire or a riot, you can vanish into the background and re-enter stealth. You do this by making a COG or DEX check as an action. You will be swiftly discovered if any creature is specifically paying attention to you, though unless that creature can alert others in some obvious way (such as with a warhorn or has a really loud voice) then you can still hide from other creatures. In more general situations, you may receive penalties to your check based on how chaotic the scene is or how observant the enemies are. Similarly, you may receive bonuses to your save if something important or eye-catching is occurring around you, or the situation is especially chaotic.


If you successfully re-enter stealth, you cannot be targeted by any enemy that does not succeed against you in a Contest (his COG vs your COG/DEX). Enemies that cannot see you are also valid targets for 'Sneak Attack'.


7:


Master of Disguise: You are a master of impersonations and disguises. When you wear a disguise, whether as a specific person or a more general type of person, such as a palace servant or a bodyguard, roll 1d20, then add your COG modifier and your Criminal Competence bonus relating to disguises, if any. This is your Disguise Number. If this number is lower than your Scoundrel level + COG modifier, you may use that number instead for your Disguise Number. Regardless If any creature sees you, that creature should roll a d20 and add any relevant modifiers. If the creature does not roll above your Disguise Number, that creature will not suspect you are an imposter, though he might grow suspicious if he sees you doing something you're not supposed to.


For example, a palace butler should not be walking around in the dungeons, but a turnkey or a torturer would be able to pass relatively unquestioned.


You can receive penalties to your disguise check if you are not the same sex or race of the creature you are attempting to imitate, or if you are an unconventional race (in general or in that area). A Deerling does not stand out much in some parts of the Equatorial lands, but is very noticeable in some of the small towns, never mind distant foreign lands. You can also receive bonuses to your check if you have props or other items to bolster your disguise, such as when you pretend to the Governor of a distant province to enter an exclusive party and you have his invitation to prove that you are supposed to be here.


8:


Danger Sense: Your instincts are so finely honed that you have an almost preternatural sense of self-preservation, allowing you to detect danger before it attacks. If you are ever in a situation and you do not feel insecure, you can tell the Referee that you'd like to make a save. On a successful save, you can observe any of the places where you might be ambushed, potential enemies nearby or other dangers around you.


Additionally, if you're about to blunder into a trap or an ambush, the Referee may call for you to save, if you could somehow detect something is not quite right. On a successful save, you are made aware of any potential observable danger.


For example, if our Scoundrel uses this ability while the party is crossing through a Bazaar, he might notice the man and woman who are pretending to browse and not to be watching them and suspect them to be members of the secret police or agents hired by one of the party's enemies. Or if the party is about to blunder into an ambush, the Scoundrel could use this ability and recognize that the narrow bridge ahead of them is the perfect place for a nasty trap, or an ambush.


9:


One Last Job: If you are ever trapped in a desperate situation with no way out, Once and only Once, you can suddenly reveal how this was all according to your unforeseen master plan. Suddenly the tables turn in your favor, and your comrades achieve victory, but your fate is left ambiguous, such as you were last seen wrestling Moriarty and tumbling off a ledge, or you were accidentally shot by your own allies at the last second, or something equally tragic. However, there is no chance this actually killed you, and you'll be back.

by Patrick Schoenmaker
by Patrick Schoenmaker

Tricks of the Trade:


1d8

1- Poison Pro. You know all about poisons, where to find them, how to handle them, how to buy and sell them, who will purchase them, which ones are illegal, etc. You also know which creatures are poisonous and how to extract poison from dangerous creatures. You start with 1d6 doses of a random poison. Roll on the Random Potion table to see what you get.

2- Trap Master. You know about traps and how to make them. Given basic materials, such as ropes, wire, heavy objects to act as weights, you can quickly construct traps, assuming you have the time and materials to do so. Roll 1d3 times on the Random Trap table to see what you know how to build.

3- Sneaky Stabber. When you attack someone who was unprepared or not expecting, you do double damage if you are using a Quick Weapon. Additionally, if you attack someone who you could conceivably kill in a single attack from stealth, the Referee may allow you to replace the damage roll with a save vs death.

4- Mad Bomber. You know the secrets of fire. If given access to an Alchemist's lab, various chemicals or a well-stocked city, you can create explosives or incendiary devices sure to leave your enemies in pieces. Roll 1d3 times on the Dangerous Devices table to see what you know how to build.

5- Knife Shark. You are really good at throwing knives. When you hit someone with a thrown Quick Weapon such as throwing knife, shuriken, or something similar, you can immediately make another attack with a thrown Quick Weapon. If you kill someone with a thrown Quick Weapon, regardless of if this is your first or second attack, you may automatically make another thrown Quick Weapon attack.

6- Archery Expert. When you make an attack with a bow or crossbow, you can immediately take a free action to move, dodge or disengage from the current situation.

7- Roguish Diplomacy. When confronted with a foe, you can try to distract an enemy. The tactic can be anything, from throwing sand in their eyes to juggling. The enemy may be granted a check to resist against whatever ability score you are using to try and distract them. Alternatively, if something is distracting enough, the enemy may simply be automatically distracted (Referee's Discretion). If the enemy is distracted, you or an ally of your choice may immediately act against them as a free action.

8- Goon Squad. You start with a free henchmen. This henchman has his (or her) own agenda and is not necessarily your friend. Roll on the Random Henchmen table below to see who you get.


Random Poisons:


1d6

1- Widow's Kiss (Injected). A poison collected from thousands of black widow spiders. Causes 3d4 damage, 1d4 per round, until a creature passes a CON save or all damage is dealt. Much feared, but not nearly as dangerous as people think.

2- Rattler's Bite (Injected). Taken from the Rattler Serpent, this poison is dangerous, but if treated, rarely results in fatalities. This poison does 1d6 DEX damage per hour. If reduced to 0 DEX, a creature must save or die. Creatures subtract the amount of DEX damage they have taken from any roll to do an action requiring skill or precision. 3- Dancing Spiral Venom (Injected). This poison is the collected venom from the bite of the Dancing Spiral Spider. Does 1 CON damage per minute or until a creature passes three CON saves. Can make 1 CON save every 1d4 minutes. If reduced to 0 CON, a creature dies.

4- Fire Coral Dust (Absorbed through skin). Created by powdering certain dangerous corals, an incredible unpleasant job done only by slaves. If this dust is touched, any creature exposed to it will feel burning pain and must make a Morale check or immediately take action to try and get this horrible dust off himself.

5- Fiddleback's Fang (Injected). Taken from the fiddleback spider, this venom rots the flesh of anyone exposed to it. Fiddleback Venom does 1d3 STR damage per minute, reducing any damage dealt by the amount of STR damage taken. If reduced to 0 STR, the exposed creature dies. Anyone exposed to this will also feel extreme pain and must make a Morale check or immediately flee and seek an antidote.

6- Lullaby Sand (Eaten/Absorbed through skin). Fine, golden dust, derived from the wings of a particularly gentle butterfly, purified and collected by children and fools. When poured onto someone, the creature will immediately become sleepy and must save or fall asleep. Eating it forces disadvantage on the save. Creatures who know they are in a dangerous situation automatically pass their saves.

Random Traps:


1d8

1- Tiger Pit. Dig a pit that is too big to climb out of. If you're feeling really nasty, cut sticks into sharp points and drive them into the ground at the bottom of the pit. Then cover the top of the trap with a layer of woven grass or branches and cover it with ground cover. Any creature that steps on it will fall into the pit and be stuck. The creature will also likely impale itself on the spikes.

2- Springpole Snare. Take a young tree that is springy and tie it back, then rig the rope to a tripwire or trigger. Tie a knife or a sharp object to the end of the tree. When triggered, the young tree will snap back and drive the sharp object into whatever tripped the trap.

3- Twitch-Up Snare. Tie a rope to the branches of a tall tree and tie a loop, then leave it on the ground. When a creature steps on it, it will jerk tight and yank them up, leaving them hanging in the air.

4- Crusher Trap. A trap that leaves a piece of bait under something heavy, such as some cut logs or a heavy rock. When the bait is grabbed or messed with, whatever holding back the heavy weight is removed, causing them to fall down and flatten the creature who took the bait.

5- Bow Trap. A bow, pulled back with an arrow nocked, is tied to a tripwire. When the tripwire is triggered, the bow fires.

6- Swinging Mace Trap. Create a large, heavy ball, occasionally with large spikes poking out of it. Attach it to a tripwire. When triggered, the giant ball will swing down and inflict terrible injuries on anyone foolish enough to get in the way.

7- Snake Trap. Create a box that will spring open when triggered. Put a venomous (and easily irritable) animal in there. When the trap is triggered, hopefully the venomous animal will fall onto and bite the creature who opened the box.

8- Guillotine Wire Trap. Take a strong piece of cord or wire and tie it across a path between two immovable objects. When enemies come, pull it tight so it rests at about neck level. If a creature hits the wire going fast enough, it will do damage to the throat and stop them cold. Best if wire is used, because it is much thinner and harder to see. Also, better if used at night.


Dangerous Devices:


1d6

1- Grenado. Your classic homemade explosives. You failed to become an Artificer, but you remember this one. Does 3d6 damage in a 30' radius, save for half.

2- Firebomb. One step up from a Molotov cocktail. Does 2d6 damage, save for half. On a failed save, a creature is also set on fire and takes 1d6 fire damage per round until they can get the burning fuel off himself. Leaves a pool of burning liquid behind and sets flammable objects on fire.

3- God's Palm. An explosive, modified to do less damage, intended to stun or disrupt. Does 2d6 damage, save for half. On a failed save, a creature is also stunned for 1 minute or until he can pass a save on his turn. Stunned creatures can take an action or move, but not both.

4- Gasbomb. An explosive that floods a 30' cube with some sort of gas. You know how to manufacture 1d4 [1= Tear Gas- no damage, but gives disadvantage on any check or save made to do anything complex, extremely painful; 2= Mustard Gas, 2d6 acid damage per round spent in the cloud; 3= Laughing gas- creatures must save or burst into gales of laughter. Talking and spell-casting is impossible unless you don't need to talk to cast and anything precise is done at -2 as you're shaking from the laughter; 4= Euphoria Gas- creatures must save or fall into a languid state. They feel great. Creatures that fail their save will need to succeed on a save to do anything but laze around in the smoke. Creatures who passed their initial save must save each round they are within the cloud.]

5- Coldsnap. Like a firebomb, except the exact opposite. Does 2d6 cold damage, save for half. Creatures that fail their save are also frozen in place and need to succeed on a STR check to break out of the ice. If thrown into water, creates a piece of ice 8' long and 5' wide.

6- Slayer. As per a normal Grenado, but designed to maim and kill. Does 3d6 damage, save for half. Creatures that fail their saves also suffer from bleed and take 1d4 damage a round until they take an action to treat their wound, either with magic or a medicine check.


Random Henchmen:


1d6

1- Babysitter/Bodyguard. He'll protect you, but his primary job is to keep an eye on you. This is because you 1d4 [1= Owe the local crime boss/loan shark an enormous sum; 2= You aren't trusted, having betrayed some former allies (but not your bodyguard's boss); 3= He's evaluating you. If you pass, you can join the Boss' crew; 4= The Boss has a parallel objective to whatever you're doing. Your protector is here to make sure the boss' interested are looked after.]

2- A sexy femme fatale. She's beautiful, dangerous and untrustworthy. She definitely has a hidden agenda. Secretly, she 1d6 [1= Has a heart of gold; 2= Actually loves you; 3= Feels nothing for you; 4= Is planning to betray you; 5= Working for you is part of an elaborate scheme that has a 50% of blowing up in her face; 6= Is being black-mailed/strong-armed/manipulated into doing this at the behest of another party.]

3- Former partner. You used to work together until 1d6 [1= Your methods disgusted him, so he left; 2= His methods disgusted you, so you left; 3= He cheated you; 4= He abandoned you when you needed him most; 5= He took the fall for you. There is a chance he is plotting his revenge or maybe he's just bitter; 6= You had different priorities, so you parted ways amicably.]

4- Estranged family member. This person is a 1d3 [1= Younger brother or cousin who idolized the criminal lifestyle. "As far back as I can remember, I always wanted to be a gangster."; 2= Older man who initiated you into the criminal underworld such as a father, uncle, older brother, etc; 3= A wife, you got into this racket because you married her, but you and her are separated because of 1d4 (1= Money, you argued over it; 2= Her loyalty to her family over you; 3= Your father-in-law never liked you; 4= She got involved in her own business and disappeared one day without a word)].

5- Old Hand. An old rogue who can't get out of the game. He's an addict, chasing the high of getting away with it. Not as fast or strong as he used to be, but he has a wealth of knowledge about everything criminal. Back in the day he was a famous 1d6 [1= Thief; 2= Robber; 3= Pirate; 4= Safe-cracker; 5= Smuggler; 6= Outlaw Mage, who practiced illegal magic. His magic may be illegal because of societal restrictions, or it may be genuinely evil black magic.]

6- A weirdo. He is 1d6 [1= A junkie, only after his next fix; 2= A secret serial killer; 3= A half-ghoul; 4= A yandere-esque stalker- he or she is obsessed with you. His feelings may be romantic, but he may just idolize you and want to do anything to earn your affections or "help" you; 5= A social outcast, someone who doesn't fit in around here, someone belonging to a different race, class, religion than the norm; 6= As "5", but is actually a shapeshifter pretending to be an outcast so people don't investigate too closely.]


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