
One of the most famous villains in all of literary history is Professor James Moriarty. First introduced by Arthur Conan Doyle, Professor Moriarty was described by Sherlock Holmes as the “Napoleon of Crime.” But despite the nature of Moriarty’s villainy, it took all of the singular genius of Holmes to even grasp that he existed, and even then over a period of months. As the great detective described it himself:
He is the Napoleon of crime, Watson. He is the organizer of half that is evil and of nearly all that is undetected in this great city. He is a genius, a philosopher, an abstract thinker. He has a brain of the first order. He sits motionless, like a spider in the center of its web, but that web has a thousand radiations, and he knows well every quiver of each of them. He does little himself. He only plans. But his agents are numerous and splendidly organized. Is there a crime to be done, a paper to be abstracted, we will say, a house to be rifled, a man to be removed–the word is passed to the Professor, the matter is organized and carried out. The agent may be caught. In that case money is found for his bail or his defence. But the central power which uses the agent is never caught–never so much as suspected. This was the organization which I deduced, Watson, and which I devoted my whole energy to exposing and breaking up.
Another famous criminal mastermind in the American lexicon is, of course, Keyser Soze in Bryan Singer’s The Usual Suspects. Unlike Moriarty, who kept himself well hidden, Keyser Soze is somebody who is well known in the criminal community, but was regarded as a myth by some, and nobody actually knew anyone who worked for him. Indeed, the major plot point of the movie revolves around not only Soze’s identity, but a plot to kill a man who could identify Soze.
Despite being such powerful literary constructs, the fact of the matter is that criminal masterminds who keep their identities hidden and operate in the shadows are pretty rare. I can only think of one who really fits the bill, and that’s London’s Adam Worth, who was supposedly Conan Doyle’s model for the character of Moriarty. This is particularly the case in America, where our criminal masterminds are more in the Lucky Luciano vein–arrogant, colorful, and well-known as a criminal. This last part is key: even if the D.A.s haven’t managed to put together the evidence against them, most organized crime bosses are fairly well known.
Why is this? You would think that, for a criminal, anonymity would be a desirable asset, especially if a person is at the head of a large, organized operation. However, the reality is that the inner workings of most criminal organizations don’t take long to be understood well by law enforcement. There just aren’t any shadowy masterminds out there–and there’s three pretty good reasons for that.
1. It’s impossible to keep it secret.
As Benjamin Franklin once wrong, “three can keep a secret if two of them are dead.” In other words, if a person wanted to run a political organization that could dominate a city, he’s going to need hundreds of people at his disposal. And face it, it’s impossible for those hundreds of people to keep a secret. If if not everybody knows who’s running the show, some people at some level have to know. Given that common criminals are not noted for their intellectual capacities, it’s inevitable that some of them are going to fail at their crimes and get caught. Eventually, one of those people is going to know the boss’s name, and as soon as he gives it, the cops will know, too.
2. For the most part, the type of people who would make good masterminds don’t become criminals.
There aren’t too many people who wake up at the age of 12 and decide to themselves, “You know what? When I grow up, I’m going to be the best criminal ever!” Of those, there’s an even smaller set that actually devotes themselves to the task. In the real world, both of these sets are approximately equal to zero.
The fact of the matter is, most people work their way into crime either by accident or desperation. They start with some shoplifting for the thrill, or they sell a little pot on the side to score some extra cash. With some folks, this is the start on the road to more crime and sometimes into organized crime. But getting to the top in organized crime mostly involves being marginally competent at criminal acts and being lucky enough not to get killed. There’s no real time to actually devote oneself to the criminal arts, there. Plus, most gangster types love to flaunt their wealth and power. Tough to do when nobody knows who you are.
See, the type of person with the discipline, intelligence, charisma, and ability to become a great criminal isn’t going to bother himself with organized crime if they grow up in the right circumstances. They grow up to be generals, politicians, and businessmen instead. Less risk and more rewards.
3. The type of organization necessary to sustain a secret criminal organization is ineffective at committing crimes.
In The Usual Suspects, Keyser Soze’s organization is said to mostly consist of people who don’t even realize that they’re working for him, but that when they did they were “always paid five times more than the job was worth.” Sound interesting on paper, but in practice, it really wouldn’t fly. How do you keep books on an operation like that? How do you control the ebb and flow of criminal activity without you and your lieutenants giving themselves away? If you don’t give yourself away, how do you enforce loyalty and discipline? It’s just not a workable system.
Another possibility is that if you wanted to keep your identity secret, you could organize your criminal operations into a cell system, similar to Lenin’s Bolsheviks or the system evolved in Robert Heinlein’s The Moon is a Harsh Mistress. The basic idea here is to have make it so that nobody knows any more than four people in the organization, thereby limiting opportunities for infiltration. The problem with this is that you are now limited to perpetrating crimes that require 3 or 4 people, tops, or you have to exert an enormous amount of precise organization from the top and hope that groups of 2 or 3 cells can pull off a job without accidentally killing each other. Not that likely, really.
* * *
Despite being somewhat modeled after a real criminal, the fact of the matter is that a Professor Moriarty simply cannot exist. The people who could pull it off don’t usually become criminals, and the logistics of the undertaking itself would mostly prevent either the secrecy or the criminality. Thankfully, this is one instance where life simply cannot imitate art.

Perhaps the shadowy mastermind types do exist, but they find it far easier to enact their evil plans in the realms of business and government, rather than having to build their own organization from scratch.
[...] “Where Are the Shadowy Criminal Masterminds?“ [...]
[...] “Where Are the Shadowy Criminal Masterminds?“ [...]
Dude, point three is wrong, wrong, wrong.
You’ve said, “The type of organization necessary to sustain a secret criminal organization is ineffective at committing crimes”.
Let’s take out the criminal component out of the above sentence, cause that is a function, not the organizational make up itself, “The type of organization necessary to sustain a secret organization is ineffective”.
How many organizations that are secret CAN operate effectively? Plenty. Intelligence agencies for one. Every country has them and they’ve been around for hundreds to thousands of years.
How do intelligence agencies work in secret? Compartmentalization and need to know. They also have counterintelligence, deception, and security. Combine these components and you have a working secretive outfit. Organizationally intelligence agencies are a mixture of hierarchy and networks. So, I have given proof of a secretive organization that works effectively (most of the time, baring intelligence failures).
Let’s substitute in the criminal function into that working definition.
Are there criminally based intelligence agencies? Hard to know, plus it comes across as a cultural/perception question. Nevertheless, Russian state intelligence agencies could be considered a criminal intelligence agency in the past (maybe even now, given the killings of various journalists). Russian intelligence in the cold war was involved in fraud, disinformation, and assassinations. Are these criminal functions? They certainly border on it. Some aspects of American intelligence agencies could be the same. The drug trade comes to mind.
I think the biggest flaw in the third point is that intelligence agencies are set up to infiltrate and gather information on “shadowy criminal groups”. Whether or not they are criminal masterminds is another question. Moises Naim’s book Illicit is a book that covers this topic in a little detail. Naim seems to think that secretive criminal networks are just import/export guys who are good at moving illicit products.