Organized Crime: History & Myth
Two weeks ago, I talked about how we should stop using thieves' guilds in our medieval/renaissance fantasy worlds because a guild hierarchy would not really make sense for a criminal organization. So today, I want to talk about three different historical modes of organizing criminal activity, as potential inspiration to replace and improve your medieval/renaissance/early modern "thieves' guilds".
You can also check out the whole series of particular historical delves into fantasy tropes by clicking the series link here.
Bandits and Highwaymen
When we think about criminal organizations, the go-to inspiration is usually the Italian Mafia as located in New York City as in the Godfather, or Al Capone in Chicago. These are highly urbanized organizations that are networked into the political and social fabric of the city. They often involve immigrant groups, providing important social services that the city fails to provide. They often have members of the police force as well as political figures on their payroll, to ensure that blind eyes are turned to any illicit activity.
But in a world that is so much less urbanized and less globalized, such as the world of the 1100s-1600s that is the stereotypical high fantasy time period mixture, this model of crime does not exist in the same way. For one thing, organized police forces did not exist, and the political apparatus was generally smaller and less bureaucratic, which meant that there were a lot fewer people to bribe. Generally speaking as well, there were fewer legal regulations to skirt; alcohol was not heavily regulated, there were not really "illegal drugs," and prostitution was either legal or at least not heavily enforced, as young noblemen were frequent clients of the brothels and so would not have an interest in shuttering them.
Instead, it was primarily rural areas and roads that were the target for criminals. Villages where everyone knew each other could often self-police, but in the spaces between the villages, merchants carrying goods from market to market were prime targets.
This form of bandits in the space between towns was the primary method of criminal activity. Merchants had more stuff to rob and fewer protections than, say, trying to rob a nobleman in their house. There were fewer people to catch you doing crime out in the wilderness than there was in a town where being an outsider would immediately put the villagers on notice. There were more places to hide in the wilderness, simply vanishing into a forest, rather than in a town.
Organized Bandits
Banditry was something that could be done individually or in small groups without larger "organized crime" structures. In fact, most bandits--like most urban criminals--were simply individuals who thought they could make a better life for themselves through thievery or smuggling or other crime than they could through legal means in town. It was simply that in a primarily rural and agricultural world, more profit could be made out in the rural areas than in the urban ones.
When bandits did "organize," it was often along ethnic or political lines. "Barbarian" tribes were the most common organized crime gangs of late antiquity, while Viking raiders were the scourge of the early medieval world.
Vikings provide a great case study for a model of organized "banditry", in fact. The general structure of a viking group was a charismatic leader, usually skilled in battle, who would rally his countrymen to engage in a raid with the promise of a share of the plunder. They would then invade a foreign land, loot what they could from the farmlands and rural monasteries, rob traveling merchants, and then return with their spoils. Though Vikings did conquer parts of England, for the most part, Viking raids were exercises in robbery.
Town walls proved the best defense against raiders of all types, which is why many medieval cities were walled. Taking a walled town involved a siege, and bandits of both the independent and larger raiding group types rarely had the patience or resources for a protracted siege and conquest of a town.
Another example of bandits comes from the fictionalized and embellished accounts of Robin Hood, and more generally, peasant revolts. When peasants were being mistreated, such as under the regency of King John for his brother King Richard the Lionheart (for Robin Hood), taking to the wilderness was a way to escape notice and consequently taxes and law enforcement. This turn to banditry was a way to still make a living, while financing a larger sort of political agenda. Particularly successful peasant bandit groups might turn into a full-on peasant rebellion, but plenty of political discontent was simply simmering in the wilderness.
Like the vikings, these peasant "rebel" groups engaged in banditry usually had some sort of charismatic leader, but without a large hierarchy beneath them. They rarely would dare invade a town, as that would bring down the army to crush them, but would instead simply hunt merchants and travelers and generally harass anyone who passed through the region. Being a nuisance was better, even for an organization, than being in control, because being in control of a town meant drawing attention.
Summary
In short, the most faithful version of a "thieves guild" for the truly medieval world is simply a pack of bandits in the wilderness, harassing the roads of your kingdom. Often, these would involve a charismatic leader--a prime opportunity for an NPC--and would have a political agenda that motivates them, even if in practice they mostly seem to be engaging in simple criminal activity. This unifying political factor can be class-based (poor peasantry turning to crime because of poor treatment by the government/nobility) or ethnic (vikings raiding territory of other cultural groups).
Early Modern, Urban Crime
Far closer to our notions of the mafia or of a thieves guild is the versions of organized crime that arise with the increase in urbanization as part of the Industrial Revolution in the 1700s. I've already talked at length about many of the social changes in the Industrial Revolution in my post about the Luddite movement.
Specifically, the increase in urbanization presents two new modes of thieves to draw from. Both of these modes could absolutely be represented in a sufficiently sized urban environment, even in a more medieval world, as they do not require powerful central governments or modern police forces to function.
The Popular Hero
One of these modes was the flamboyant, popular criminal. Jack Sheppard is the most famous version of this, though the mythological Robin Hood absolutely draws influence from this version of crime.
Jack Sheppard was a criminal active in the 1720s--so a little later than the medieval/Renaissance/Early Modern mixture of most high fantasy, but not so late that industrialization was truly entrenched. The first railroad had not yet been invented, but London's population was certainly booming.
Sheppard gained popularity for his flamboyance. He seemingly could not be confined or prosecuted. He escaped from one of the most infamous prisons in London four separate times. In his fourth famous arrest, he showed his jailers how easy it was to pick the lock of his chains to escape, telling them how their measures were insufficient; he was subsequently locked up further, and then proceeded to still pull off an escape. His final capture, two weeks after his fourth escape from prison, came after he robbed a pawnbroker and stole a gentleman's set of clothing, and then went around town very openly, going to his favorite brothel to await his arrest.
This version of a criminal is not particularly organized. These heroes are typically individuals. If they have help or a "gang", it is usually a network of informants and safehouses, rather than other people actively engaged in crime themselves. They're often generous, either spending frivolously in a community or even just giving out money (as Robin Hood's "steal from the rich, give to the poor" mythology includes), which earns them further community protection from the authorities.
This mode of criminal relies on doing "good crimes"--things like robbery, not murder. For the popular hero criminal, one's reputation among the lower classes is key to your survival in an urban environment. Committing violent crimes is more likely to see your support, and therefore your "gang" of supporters and safehouses, dry up.
The Mastermind
By far the most "organized" version of the early modern organized crime comes from the way that police work was handled in a world before modern policing was really invented and where the royal authority was never quite as "absolutist" as it was in neighboring France. Our example here is the story of Jonathan Wild, who is one of the coolest historical criminals that I think has ever lived.
Wild was a "thief-taker" professionally. Law enforcement at the time, contemporary with Jack Sheppard, was largely done through bounties. A reward would be offered for the capture of a known criminal, and civilians could then capture those people and turn them in, rather than there being a dedicated police force.
Wild was one of these capturers, and he made his living turning in thieves that he had evidence against. However, he used this legal work as a cover story for being a major fence of stolen goods. For a small fee, he'd offer to find peoples' stolen goods for them and see them returned. Thieves could sell what they'd stolen to Wild, who would pay them; victims of theft could pay Wild for their goods, which Wild had just bought, to be returned--for more than Wild would pay the criminal--and he would pocked the difference.
Wild kept a ledger of all the criminals that he worked with, making a cross next to their name once he had taken goods from them and had proof of their illegal activity. If a thief ever turned on Wild, or tried to demand too high a fee, or tried to fence goods to anyone other than Wild, he would send out agents to capture the thief and turn them in, collecting the reward from the government. He was playing both sides. And when he did, presenting evidence sufficient to convict them, he put a second cross next to their name in his ledger, showing he had betrayed them and stopped working with them. This is the (apocryphal) story of the origin of the term "double cross", which I think is a much better story than the more likely etymology of the term.
Wild relied on a whole network of thieves, like an early mafia. But it was not a top-down organization, like the mafia. Wild was not calling in hits on people; he was acting as a fence for stolen goods, primarily, but with enough of a legal veneer as a thief-taker that he could avoid suspicion and have a way to punish those who betrayed him.
And Wild was not a guild master. There was no training element, no apprentice/journeyman/master thieves. There was no quality standards he was enforcing.
And for me at least, Wild's sort of fence network is really cool and interesting, in large part because it uses the legal system to its advantage. It is a way of twisting the legal system of the day to help out the criminals. I'd say it's more interesting than a sort of generic "guild of thieves", and more period-accurate for a world that does not have a modern police force. Plus, it allows you to develop an interesting NPC who is happy to play both sides, to help the party commit crimes but also who has the respectability to use the legal system to challenge the party.
Plus, you can make the "double cross" story true in your world, rather than apocryphal, and honestly, why wouldn't you choose to do that? It's such a fun story, and it's a shame that it is probably not the true origin of the phrase.
Conclusion
Hopefully you have enjoyed these three different, more historical modes for criminal organizations to replace your "too modern" mafia groups and your "too nonsensical" so-called guilds of criminals: rural, politically-motivated bandit groups; a popular individual criminal with a network of allies and protectors in the community; and a sort of thief-taker fence with an association of criminals that all do not dare cross him, and who straddles the line between crime and law, playing both sides.