Bandits!

Who doesn't like bandits?...

Most people, actually. They're usually boring cannon fodder. That is BAD. Bandits should be scary. Murderers and extortionists should be scary. If they can't pose any threat then how do they exist?

((EDIT: This statement was dumb. Of course people love bandits. I love bandits! But I don't like generic nameless bandits. Those are dull.))

Now THIS is a bandit!
Akira Kurosawa's Seven Samurai

They should also, notably, be people. Living, breathing, talking people with desires and goals and tactics and all the things that make people more interesting than rabid wolves.

Each Bandit Gang has three big shots: The Talker, The Bruiser, and The Leader.

Each Bandit Gang has a Tactic, an Edge, and an obvious Drawback.

The Talker is likely the first person you'll meet: they're the one who's going to try and convince you that it's a better idea to hand over your money than to come to violence. If diplomacy is necessary, they'll be involved. They bribe the officials. They talk to travelers and locals for information. They threaten and coerce.

The Bruiser is the biggest baddest most psychologically daunting fighter they've got. When things come down to a fight they're the one that'll carry it. Losing them (as well as The Leader) will prompt a Morale roll.

The Leader is the senior bandit. For whatever reason they're the one that makes big decisions. They  command respect, or fear. They get the biggest share. Not infrequently they'll have military experience. When it comes down to tactics and strategy they'll be the opposition.

Tactics are how they extort and fight.

Edge is their strength.

Drawback is a possible weakness, among others. Never assume they have just one weakness, but keep in mind the obvious one listed here.

Some more excellent bandits!
I am quite the fan of the "I need armor but it's really hot outside
so let me put this breastplate over my bare naked skin" look.

BANDITS!

These ramp up in ridiculousness as the list progresses. Stats for bandits:

Standard Bandit/Talker

AC As Leather + Shield  HD 1  HP 1d8

1d6 Weapon

Bruiser

AC  As Plate  HD 3  HP 15

1d12 Weapon

Leader

AC  As Chain + Shield  HD 3  HP 12

1d8 Weapon

Standard bandit gang size is 5-40. Don't expect for them to fight if they're outgunned. Bandits never try to take on anything they couldn't stomp with minimal casualties. They will not fight fair.

1. Tax Collector Masquerade

Talker: Phillip - A very dirty person. Clearly infested with lice. Far better at making demands that actually keeping a coherent story. Sympathetic but firm when he needs to be. Relies on Goward to save him in bad situations.

Leader: Gowald the Elder - Mastermind of the gang. Missing his left leg. Sits on the sidelines. Big-jawed and smells of pipe smoke. Needs to constantly coach Phillip and the others at their roles.

Bruiser: Frederick the Reckless - Tall man with long reach. Constantly grinding his teeth hard enough to hear. Little patience, paranoid.

Tactic: Pretend to be tax collectors and extort people for money and goods. Given taxes tend to be so arbitrary and unpredictable anyways, this is easy to impersonate.

Edge: Official documents and seals stolen from a legitimate tax collector.

Drawback: Half of them have scale mail pilfered from the tax collector’s guards. The armor still has holes and blood stains from when these bandits killed them.

2. Horse Bandits

Talker: “Hill Dwarf” - A very angry man who makes very angry threats on behalf of The Duke. Loves waving his sword around like an idiot. Near-always blushing like a beet.

Leader: “The Duke” - His enormous mustache matches his ambition. Minor nobility turned rogue. Strokes his black beard often. Rules through intimidation. Makes examples. Would rather send his entire gang to their death and mutilation before defeat.

Bruiser: “The Quick Arrow” - A crack shot with a bow, while mounted no less. Long beautiful hair and piercing eyes.

Tactic: They’ve come to steal the barley! Pillage, loot, and kidnap seasonally and sleep off the rest of the year.

Edge: They have fast sturdy horses and a mountain lair to retreat to.

Drawback: They only come around once a year (twice if they’re bored). And they appear at particular villages on a very consistent schedule. The locals hate them, and the villages can be fairly defensible when some effort and know-how is put to it.

3. Knights of Poor Job Prospects

Talker: Sir Bartholomew - A liar and a cheat, fond of dice games and abusing the powerless. Manicured fingers and parted hair, with a face you just want to punch.

Leader: Sir Roland - A mercenary turned minor nobility, just biding his time until another war comes along. Big white blood-stained beard and smell likes booze from 20 feet away. Notorious for "splitting his enemies in twain!"

Bruiser: Sir Roger - A perfect exemplar of chivalric knighthood: fast, agile, tough, loyal, robust, and utterly sociopathic. His helmet and breastplate bear roosters insignias.

Tactic: Intimidate while gaining better position, then strike hard and fast. Take valuable hostages. Kill the rest. If negotiating, stay true to their words if dealing with nobles. If dealing with peasants, they have no qualms about betraying their agreements and slaughtering everyone anyway.

Edge: They are well-equipped. All but one or two of them are equipped in half-plate with weapons of war (poleaxes, warhammers, warbows).

Drawback: They have actual knighthoods, which means that they are subject to higher laws than you. It also means they can likely be whisked away if brought promise of richer plunder, and amnesty.

4. The King’s Men

Talker: “Pretty Boy” Rolof - Good looking chap with a smooth voice and a killer smile. Likes to be cheeky and vague with his threats, while appearing outwarding nonviolent.

Leader: Anson DeFair - An idealist of a bandit. More of a brute than he cares to recognize. Always finds a way to rationalize his violence to his men. Formed a cult of personality. Charismatic silver fox with well-groomed beard and ponytail.

Bruiser: The Green Wastrel - A lithe and well-dressed fellow. Quick and witty at his remarks. Always accepts surrender and violence both. Fond of elaborately-feathered hats.

Tactic: Have the Talker confront travelers. Ask politely for money. Say it’s a “charitable contribution for a good cause”. Inform them that there will be consequences if they don’t comply. Let them go on their way if they refuse, then bushwhack them. Fight from maximum range and cover once the Talker has gotten out of the way.

Edge: Good positioning, good cover, good camouflage, and accurate longbows.

Drawback: If you can demonstrate that you’re poor, or devout Royalists, they’ll let you go scot-free.

5. Home Alone

Talker: None

Leader: A wild-savvy white-bearded old hermit. Totally anti-social. Suffers dementia. Nobody knows his name, even him.

Bruiser: None

Tactic: Booby traps everywhere. Everywhere. On the road, in the forest, along routes well-travelled and paths nobody in their right mind would take. Pit traps under pit traps. Punji sticks, trip wires, log traps, land mines, the list goes on and on. Picks valuables and food from the bodies when they’re dead and he can smell the rot.

Edge: He is the best trap maker in the world. The traps are genius and well-placed and numerous. His forest is a death trap.

Drawback: Old age. The hermit is old, and not long for this world. He is terrified that death will come for him at any moment, hence the traps. He hopes to trap Death and bargain with it, but the thought of confronting Death strikes an existential terror.

6. Brotherhood of the Beer

Talker: “Uncle” Jack - a portly and rosy-cheeked man with a habit of telling good stories. Doesn’t do the killing himself but he watches, unblinking. Crux of the gang.

Leader: Dugan - A skinny non-talkative man missing an eye. Says he lost it in a farming accident (mule kick). A victim gouged it with a finger it while he was strangling them. Watches and strategizes. Gives the final signal to kill.

Bruiser: “Little” Luna - small broad woman. Long pigtails. Takes the toughest looking person. Knows all the places to get a knife through.

Tactic: Make a very cozy camp. Welcome travellers to stay with them for the night. Get people off their guard by telling them stories and being generally rosy. Offer to take the second watch. Kill everybody in their sleep.

Edge: Their talker is a very charismatic guy. The sort of guy you want to have many drinks with. You want to listen to him late into the evening. He’s your bud!

Drawback: There are quite a number of weapons hidden around the camp - in bushes, buried in loose soil, hidden under too many clothes for this few men. There might be a body, too, not too far. Maybe they didn’t bury it and it’s starting to stink...

7. Pox Looters

Talker: Lun Caster - Doesn’t do much talking, but plenty of plague spreading. Permanently hobbled. Has immune system that keeps him constantly contagious and infected.

Leader: Able - More a de facto leader than a proper one. The eldest of the group - an old cynical woman and a survivor.

Bruiser: Percy - A cruel blade. Prone to mood swings between joking and horrendous random violence. Talks up a storm about his martial prowess, but only kills people who can’t fight back. Blonde-haired teenager brought up in a better place.

Tactic: Get Lun to smother the travellers in ultra-contagious germs by coughing/sneezing on them or such. Trail them for several days. Hit ‘em when they’re at peak incapacitation with knives and hammers.

Edge: They’ve developed an immunity to the sickness. They’re also very patient.

Drawback: Poorly equipped and unable to take anyone on in a fair fight. They’re more looters than bandits. They have small families that travel with them.

8. Saint’s Chosen

Talker: Proselytizer Gom - A fiery bellow-gutted preacher. Hides threats in promises of salvation. Demands you respect Saint Lisa.

Leader: Saint Lisa - Trialed by a censur-swinging boy and protected fanatically by her troops. Claims to be the reincarnated patron saint of travellers. Half-true. She is the reincarnated patron saint of highwaymen.

Bruiser: Decklin - Crazy eyes, never says a word. Bare hairy back shows off flagellant scars. Carries a spiky nail stick.

Tactic: Request “alms”. If not given, then three scouts stalk the marks until nightfall. The gang strikes at night.

Edge: Saints bones tied to their ramshackle armor. Each bandit has one bone which prevents the first instance of damage and then shatters.

Drawback: They aren’t really pious, but nobody in the gang wants to be perceived as such. If confronted with actual piety they will hopelessly flounder about with their moral justifications.

9. The Troll Hagglers

Talker: Buse - Likes to smile, missing all his teeth. Enjoys big exaggerated arm motions and cartoonish mockery of the troll eating peoples’ legs to supplement his threats - gumming on his forearm, simulating the troll eating a leg, is his favorite.

Leader: “Diggy” Smith - A stocky dark-browed man who likes to chastise Buse at every opportunity. Never talks to Dug directly - always through Buse.

Bruiser: Dug, Cave Troll. Has a fondness for eating legs. Not picky about the source.

Tactic: They have a cave troll! Their entire negotiating tactic revolves around haggling you down from having the cave troll eat all your legs, to you giving them money and giving the troll a non-leg-based meal.

Edge: The cave troll, of course.

Drawback: The cave troll isn’t exactly loyal to the gang. They’re just the best facilitators of leg-eating that he’s got. Won’t betray them unless a more guaranteed source of edible legs is given.

10. Zeus Crab-Tower

Talker: Hugo - wizard’s apprentice, if by chance it comes to negotiations. Hopes Jargus will die soon so he can co-opt his secrets.

Leader: Jargus the Bright, Lightning Wizard. Given most of his body for power - crab claw arm and horrible gait.

Bruiser: A giant hermit crab that lives in a wizard’s tower. Jargus calls him “Charles”.

Tactic: Hastily move the crab to key crossroads junctures. Wait for travellers to come within range. Strike them with lightning bolts. Have the giant crab move over and scoop them up and eat them. Some time later it poops out the remains into the tower for collection.

Edge: The tower enhances the range of his lightning. He can accurately strike targets up to 2 miles away.

Drawback: With the proper command spell, or perhaps a solid understanding of demolition, could collapse the tower in moments. The whole structure is a shell, swaying in too strong winds and overly hollow on the inside.