Dandy Highwaymen: street gangs and street fashions of the Wicked City

When every law is unjust, and every official is corrupt, then what place remains for the criminal?

Given that the Wicked City is already effectively a gangster state, it might be thought that few roles remained for organised crime. The city's government is little more than a gigantic protection racket, and all kinds of enterprises that are forbidden in most other places - gladiatorial death matches, the sale of noxious narcotics, and so on - are legal in the Wicked City, as long as you have the right licenses and permits. And yet criminal groups proliferate, ranging from gangs of pickpockets and petty thieves, to formidably organised mafias which virtually function as semi-official government departments, to neighbourhood defence associations that exist to protect and avenge the people of a specific community in the face of the cruel indifference of the official authorities. For better and for worse, they step into the gaps created by the chronic malfunctioning of the city's government; and in many places, the rough-and-ready justice meted out by the local mob is a much more important and reliable source of social order than the arbitrary laws enforced by the King's Men.

It is true, however, that the city's government soaks up many of the kinds of people who become criminals in other nations. Anyone with a taste for thuggery and extortion can easily fulfill it by joining the King's Men, rather than risking any kind of criminal endeavour; and as a result, the city's gangs tend to be made up of the kind of misfits and individualists who struggle to fit into even the most corrupt of official authority structures. Incorrigible rule-breakers and iconoclasts, quixotic vigilantes and hair-trigger psychopaths; these are the kinds of people who fill the ranks of the city's multitude of criminal gangs. It is perhaps because individual self-expression is so important to so many of them that the city's gangsters tend to be a dandaical bunch, who advertise their status by cultivating foppish and exaggerated fashions which are pointedly at odds with the violence by which their positions are maintained. They wear their wealth on their sleeves, sometimes literally: the more successful the criminal, the more extravagant their clothes. Huge hats and turbans, brightly coloured fabrics, ornate watch-chains, and pointed shoes are as much a part of the city's gangster aesthetic as the knives and pistols thrust into their elegantly-tailored belts. Among the city's high society, it's the Cobweb families who are the trend-setters; but out in the streets, everyone wants to dress like a gangster.

Basically these guys, but in Early Modern Central Asia.

To generate a random street gang (and their amazing clothes), use the following table:

Size (roll 1d6):

1. Very small. 2d4 toughs in fancy hats. May all be members of a single family.
2. Small. 1d8+4 people leagued together in some shared criminal enterprise. 
3. Average. 1d12+6 active members, who may lay claim to a small area of the city.
4. Large. 1d20+10 active members. Probably act as the de facto authority in one or more communities out in the Streets.
5. Very large. 2d20+20 active members. Most gangs at this level of strength have come to an arrangement with the King's Men, who subcontract 'tax collection' (i.e. extortion) duties for one area of the city out to them in exchange for a cut of the profits.
6. Huge. 4d20+30 active members. Probably run a whole range of criminal enterprises simultaneously. May lay claim to an entire district of the Streets.

The local mob.

Signature Fashion (roll 1d10 and 1d12)

1. Huge...
2. Brightly-coloured...
3. Striped...
4. Extra-wide...
5. Fur-lined...
6. Spectacularly embroidered...
7. Subtly understated...
8. Sharply-tailored...
9. Ribboned and tasselled... 
10. Exquisitely pointed...

1. ...turbans.
2. ...hats.
3. ...capes.
4. ...shoes.
5. ...coats.
6. ...scarves.
7. ...gloves.
8. ...sashes.
9. ...masks.
10. ...waistcoats.
11. ...trousers.
12. ...robes.

I'm the dandy highwayman whom you're too scared to mention,

I spend my cash on looking flash and grabbing your attention...

Signature Accessory (roll 1d20)

1. Knives with fancy handles.
2. Ultra-long tobacco pipes.
3. Beautiful painted fans.
4. Stylised make-up.
5. Complex full-body tattoos.
6. Jewelled snuff-boxes.
7. Waxed moustaches.
8. Hair worn long and loose.
9. Hair worn in elaborate braids.
10. Long, pointy beards.
11. Ostentatious pocket-watches on chunky gilded chains.
12. Rings on every finger.
13. Jewelled earrings.
14. Duelling scars. (Gang members without them pick fights with each other all the time until they get suitably scarred-up.)
15. Beautiful lacquer boxes containing drug paraphernalia. 
16. Gold teeth.
17. Enormous gold belt buckles.
18. Painted and beautifully-manicured fingernails.
19. Eccentrically-scented colognes.
20. Collections of holy charms, semi-ironically worn around the neck.

Gang lookout relaxing in the ruined districts. Painting by Andrew Geddes.

Primary activity (roll 1d20, or 2d20 for very large or huge gangs)

1. Pickpocketing and petty theft. 
2. Burglary.
3. Banditry and highway robbery.
4. Fencing stolen goods.
5. Coining.
6. Forging - run a workshop crafting fake art objects, antiques, documents, etc.
7. Running unlicensed gambling dens.
8. Running unlicensed brothels.
9. Running unlicensed pit fights.
10. Information-gathering and blackmail. 
11. Cooking and dealing drugs. (Invariably impure: people who can afford the good stuff just go to the Serpent Folk.)
12. Hired muscle, no questions asked.
13. Black magic - put curses on people who don't pay them off, will curse your enemies for a fee.
14. Cogslicing - the forcible reprogramming of kidnapped or captured automata, most of whom are then sold on as labourers. Detested by the Brass Folk, who regard it as a crime worse than murder.
15. Protection racket.
16. Smuggling.
17. Contract killers.
18. Kidnapping - rich victims are ransomed, poorer ones are sold into slavery.
19. Protecting the interests of a single neighbourhood or ethnic group, usually at the expense of their neighbours.
20. Vigilantes, who mete out rough-and-ready street justice in the name of their community. Regarded as local heroes.

Painting by Jean-Léon Gérôme.

Special Asset (roll 1d20)

1. Mostly-sane Shining One who acts as the gang's scout and lookout.
2. Crate of stolen clockwork monkeys, which the gang uses as covert messengers.
3. Connections to Red Brotherhood, to whom they secretly feed information in exchange for occasional assistance in emergencies.
4. Connections to the People of the Rubble, who offer them escort and shelter in the Rubble in exchange for gifts and goods.
5. Have a stolen printing press in a basement, and know how to use it. Have a sideline in printing seditious literature for pay.
6. 1d3 gang members belong to the Unkindness, and their ravens act as spies for the gang.
7. Have taken over and partially repaired a large ruined building out in the Streets, which they use as a fortified base of operations.
8. Have mapped out a network of tunnels in the upper levels of the Maze, and use them as hideouts and a means of covert movement through the city.
9. The gang's members are devout (if not exactly righteous) believers in one of the religions of the Great Road, and the other members of their religious community are willing to offer them support and shelter in exchange for protection and a tithe of their profits.
10. The gang has stolen some clockwork hardware from the city's military - for small gangs this probably just means things like chatterswords or clockwork wings, but larger gangs might have a suit of steam knight armour, or even a stolen gyrocopter or mech.
11. 10% of the gang's members are Maimed, whom they use as spies and enforcers.
12. Nest of semi-tame brass-snout rats in a basement, whom the gang uses as guards and attack dogs.
13. The brother of one of the gangsters is a Golden One, who patches up wounded gang members in emergencies.
14. One of the gangsters is a renegade Steel Aspirant, who grafts crude clockwork prostheses onto the gang's crazier members.
15. The gang has some compromising blackmail material on one of the Cobweb families, and is able to extort occasional favours out of them in exchange for keeping quiet.
16. The gang has connections to one of the villages in the countryside outside the Wicked City, and the people there are willing to hide them from the authorities when they need to lie low.
17. The gang has a contact in one of the city's merchant houses, who feeds them information about poorly-guarded warehouses and juicy incoming shipments.
18. The gang has a contact in the Ministry of Civil Order, who warns them of upcoming busts and raids.
19. The spirits of the Streets seem to have adopted the gang as part of their weird nocturnal ecosystem, and by night the streets and houses will rearrange themselves to help them rather than to hinder them.
20. One member of the gang is an intelligent clockwork octopus. (And, yes, he takes fashion just as seriously as the rest of them!)

Every girl's crazy 'bout a sharp-dressed man... (Painting by Rudolf Weisse.)

Current Leader (roll 1d12)

1. A Blood Man, thrown out of his regiment for insubordination, who brawled his way up the gang's heirarchy and now dreams of accumulating enough wealth to enchant his own cauldron and start brewing up a regiment of his own. 
2. A renegade Serpent Folk poisoner who has burned her bridges with her community through the rather reckless application of her skills. Her alchemical abilities are mediocre, but she's a very good shot with a poisoned blowpipe. 
3. An amateur clockworker, self-educated but possessing considerable talent, who has rigged up a variety of crude clockwork traps and automata to assist the gang in its endeavours. His followers all carry cogworms, which they use to steal power from untended machines at every chance they get.
4. A fearsomely driven woman who secretly belongs to one of the cults of the Blue Necropolis, and hopes to use her gang to procure enough victims to empower the being that she believes to be a great and benevolent queen from the city's past, but is actually just a ravenous Hortlak horror waiting for a chance to gorge itself on human flesh.
5. A deserter from the city's armies, who found that criminal life suited him much better than a military career. His military experience is a real asset to the gang in turf wars, and he still has a lot of friends in the King's Men who are willing to help him stay out of trouble with the authorities.
6. The latest scion of a well-established crime dynasty, whose family has been running this gang for generations. Its members don't always agree with her decisions, but find the idea of anyone else being in charge more-or-less unthinkable. 
7. An escaped slave from the city's foundries, horribly scarred by the burns of hot iron that he endured during his years of hellish forced labour. Enormously tough and more-or-less immune to pain. He has nothing but hatred and contempt for the city's authorities, and longs to see the King's Tower levelled with the dust.
8. A renegade from the distant and half-legendary Sunset City, who fled her home years ago under circumstances she doesn't like to talk about, and didn't stop running until she reached the Wicked City. She has an excellent head for business, and the glass daggers and bladed chopines she brought with her from her homeland ensure that she can hold her own in a knifefight. 
9. A steppe nomad who originally came to the Wicked City as a horse merchant, and drifted into criminality after he failed to bribe the right officials and had his business confiscated by the city's government. The city's not much of a place for a horseman, but he's an excellent archer and a brutally effective wrestler. Under his leadership, the gang has adopted a rough-and-ready version of the warrior code of his far-off homeland, and consider themselves honourary steppe warriors - a claim that any true nomad would find ridiculous. 
10. A huge and heavily scarred woman, the veteran of a hundred pit-fights. Born into wretched poverty, she turned her strength to account in the most straightforward way she could find, by fighting for money; ultimately, she earned enough gold and reputation to set up a criminal enterprise of her own. Her renown as a near-invincible fighter is a major asset to her gang, helping her to intimidate their rivals into submission; but she's not as young as she once was, and she fears that one day someone younger and faster is going to call her bluff. 
11. A Brass Man, who has never been quite the same since he took a heavy blow to his brain-case. Abandoned his community for a life of crime and eccentricity. Builds abstract and weirdly beautiful clockwork machines in his spare time. 
12. A spiteful young woman who was born into one of the Cobweb families, but managed to alienate all her relatives and was ultimately disowned. Puts on a good show of imperious authority. Fantasises about the day she will return to her birthplace at the head of an army of cutthroats and reclaim her birthright at knifepoint.

Painting by Jean-Léon Gérôme.