I am aiming to write a novel in a noir style setting in a fictional city in the west coast about a sleazy, leisure suit wearing private eye who runs investigations out of his office in rather retro penthouse in little Athens. Besides the usual adulterous spouse or investigating insurance fraud my Character would also investigate things for the local Criminal syndicates of the city, which means dealing with a variety of Bosses of said organizations. My question is how do i make these heads of the organizations realistic and not run into just copy pasting Don Vito while still making them interesting characters.
Welcome to the site! For research, I've found that googling "misconceptions about X" tends to get better results than just googling "X." Googling "X" gets you a lot of people who talk about X without knowing anything about it, but adding "misconceptions" gets you the people who look at two different viewpoints with an eye specifically for seeing which one is more valid than the other. For characterization, the most important thing in general is to make them different from each other I also have a specific method that I talk about a lot here, do you want me to PM you so I don't clutter up yet another thread for everybody else?
If I were doing this, I'd probably start with a character who sees himself as a good man with responsibilities, making some regrettably necessary compromises to fulfill those responsibilities, but still with some strong moral/ethical standards, and empathy, that the reader can identify with. He commits crimes and kills people, but he doesn't see himself as a criminal or killer. And that largely describes my male protagonist... This is not precisely a surprise, but.
Crime bosses are really just entrepreneurial businessmen, the difference is they have no morality. They still suffer from the stresses of running a business, and family issues. Lazy workers. The pressure of staying ahead of the law. Don't think of them as superhuman villains, think of them as the guy who runs that private taxi firm in town. Do you have family members who own their own business? It's them, but with no scruples.
I must admit I am tiring of the stereo-typical crime boss. In fact I have the same dilemma as I'm struggling to make mine original too. The thing is they're nearly always portrayed in the same way - ruthless, but intelligent, outwardly dignified and polite. How many times have we heard a crime boss say to the protagonist something like, "Mr Smith, there's no need to get excited. Can we not discuss this like two civilized individuals?" They're always shown as cultured, or lovers of fine wines or music. I know all this is done to serve as a kind of juxtaposition to their murdering and other criminal activities, but it's a little old now. The intelligent thing is a difficult one to avoid - most crime bosses, as @JE Loddon rightly points out, are entrepreneurial businessmen - but it would be nice to see a crime boss who's badly dressed, undignified and ugly, and who doesn't speak in a calm measured way all the time.
I would say think a mob as a pack of wolves, should the alpha show weakness another will challenge him for the position. Reputation is as important to as proof of success (such as finance) which is why a certain image comes to mind when we hear the words 'mob boss' or 'crime lord'. They have the intelligence of an entrepreneur but they do not stick to the bindings of law. Now, the thing to remember is that your mob boss is going to portray what he feels is safe to do so. If he doesn't trust your PI, then odds are he'll try to put your protagonist in a position that he has to comply. If they're in a position of God rapport and the mob boss feels it safe, he might show a more human side. You need to establish his nature and really get into his head to answer this.
As far as the Mob goes, I've read reports where they're getting smarter. That is to say there are more "higher degrees" in fields like business, law, and medicine than there used to be. They've also gone high tech. Even cartels like Los Zetas have computer geeks in their ranks. Most of my research lately has been in the South American and Central American cartels, who will occasionally do business with the Mob, though historically the Sicilian Mafia didn't want to get involved with drugs. They did, though, and it triggered a full-scale war in the 1970s and 1980s. Most of the bosses have been short-tempered, easily offended types, but they're not stupid, usually. They are almost always ruthless, because you don't become a made man without having killed somebody, and you don't get to be the boss without killing several somebodies, personally.
One of my concepts was adding a surprisingly influential greek mob in Little Athens which operates in the Night Life of the city with Helios "The Greek" Georgiades acting as the Godfather of the night. Helios acts as a patriarch of sorts for the Georgiades mob, which in itself is made up of smaller greek-american criminal clans that are formed in a loose confederation of sorts with vested interest in defending Greek control of the Underbelly of little Athens. Helios himself views his organization as a family legacy he must preserve, he is the type of man even though he prefers not to use violence, but when he does he does it in a quick, quiet way as to not attract attention to himself. He prefers to keep the operations under the cover of night and underground as to not attract unwanted attention to the organization, which besides the night club elysium also includes illegal casinos, running party drugs such as molly, and even other less savory operations including the typical extortion and racketeering. At heart he is a family man who has a unquestioning loyalty to family, which includes many of the other clans in the organization seeing as alot of them tend to be related by marriage, but leaves him very easily harmed by those close to him, especially those who are kin. He spends most of his time in thought and hardly ever gives any idle talk and keeps himself as obscure as possible. But the Helios's organization is showing cracks, their is rumors among the organization that someone within the clans is planning a coup of sorts to out the Georgiades family from the head of the clans, which would inevitably cause a civil war among the clans. This along with the disappearance of Helios son and provocations by the Bratva has driven him to hire outside help...A seedy private investigator who lives in a penthouse right in Little Athens. Hopefully his decision will pay off, if it does not...Little Athens will burn.
Do yer research. While I've not written about any crime bosses I've read some factual books that have given me a pretty good grasp. I recommend you start with Cosa Nostra and Making Jack Falcone. Hope that helps
I suggest hitting the books at a local library, books are often more reliable than what you read online. Check the historical section.
