Like any large city, Midwinter has it's fair share of criminals and naer-do-wells. In Midwinter the vast majority of thieves and rogues are members of one of the various Gangs.
For generations, the city's underworld had been run by the Shadow Guild. In 1021TA a new group of thieves, called the Black Rose, began to interfere with the Shadow Guild's activities outside of the city. In December 1021TA the Black Rose began it's infitration of the city's Harbour district. Fierce fighting between the Black Rose and the Shadow Guild breaks out. In June of 1022TA, the Black Rose succsfully oust the Shadow Guild from the Harbour district.
Initially confined to the sewers, the conflict soon boils out onto the streets of the city. In an attempt to curb the fighting, the Shadow Guild Grandmaster calls a ceasefire with the Black Rose. The uneasy peace takes hold in the New City but in the Old City another thieveing mob, the Red Hand, raises it's banners. Originally a smuggling band forced out of the city two hundred years ago, the Red Hand begins to disrupt Black Rose shipping and diverting it to the Docklands.
The Black Rose begin to retaliate and move into the Docklands. Soon, the gangs begin fighting again. The Docklands chapter of the Shadow Guild try to broker a peace between the two gangs, but when their Guildmaster is killed the chapter splinters into dozens of small gangs. The rot soon spreads and by the end of 1022 the Shambles Chapter has also collapsed.
The peace in the new city lasts only a few months. An unknown assassin kills Otto Hansen, the Shadow Guild's Grandmaster and shortly after the Guildmaster of the Norn Hill chapter is killed along with most of his entourage. Within six months, the Shadow Guild has all but disappeared and a dozen new gangs have sprung up across the city - all fiercely guarding their turf.