Does anyone have any ideas how a criminal character would develop underworld contacts? I'm trying to write something like this in a believable manner however I no experience with organized crime (fortunately), so suggestions would be appreciated.
Casual encounters are one way. I did a favor for a friend of an employer once, he turned out to be a low level mob guy in Chicago, and very grateful for the gesture. Take a look at the movie Donnie Brasco. That’s all about a cop infiltrating the mob and making new contacts and working his way up the ladder.
Think of the issue the other way around. Imagine you're writing a story of a crime boss who wants new recruits. How would he go about getting them? One way would be to ask his existing 'staff' if they know anyone who could help out occasionally. Such an organization may be wary of volunteers.
I like the childhood friend route. If I was to write something similar, my character would probably hang around sketchy areas and asking people around, a bar or pub of sorts. Criminals are everywhere and I've seen it quite often that people got involved with organized crime. You could have your character meet someone randomly, helping out to fix your car or similar, and have that new character "know a guy."
Around here for some reason I keep hearing rumors that many of the used car dealerships have shady underworld connections. Or maybe contact a cheap public defender type law firm that has a reputation for defending the guilty. Or start at the literal street level—go to a street corner in a really bad neighborhood where they sell weed or crack and buy some, then put the word out that you're looking to make some connections.
So, what i really like about the first book of the Mercy Thompson series is that it really seta up how she (Mercy) meets these contacts. Its not really a "real world" thing, what with vampires and all, but hear me out! Mercy is a mechanic. The vampires are like mobsters. The mythical creatures that live amongst the humans must pay the vampires for protection (from them!). Mercy' previous employer had dealings with them, and when she took over the shop, she now dealt with them. She traded services (fixing their cars) for them leaving her and ber business alone. She know who and what they are, but business is business. She even becomes friends with one of them, bonding over their love of restoring old cars. One day, she needs help. So she calls up the vampires/mobsters, and they are willing to help. Provided she return the favor. They become a contact as well as her previous employer who has dealing with a bunch of otherworldly things too. So, if we take out the vampire part.... Your MC could have a close working relationship with them, that turns into a contracted relationship. Or they could work for someone who they find out does some low grade shady stuff.
I remember in high school my parents asking my sister about buying drugs and her telling them that well she didn't do them, she could get pretty much anything in a day or two if she wanted it. You know who the druggies are- you approach one and ask for what you need, they can either get it o direct you to someone who can. It's all about contacts. I assume if he's already a criminal, he already has others he knows who are also criminals. Lots of gangs are wary of outsiders, but a friend of a friend of a friend can get him in the door. I would expect that most criminal organizations would make him do jobs to prove his loyalty and worth(and make sure his hands are as red as their's) before letting him get too involved.
Criminal organizations function the same way businesses do. Differentiate between in-organization contacts, external contacts and rival contacts. Usually, someone will first interact with a contact from one precise organization, and this will forever define their perspective/picture as a first impression. The first contact is what counts the most; which can be through various means. Curiosity driving someone to experiment with drugs and thus approach the dealer of a cartel. Lust driving someone to hire a hooker and be involved with their greater network. A desperate man refused his loans by banks approaching a usurer. A vengeful man seeking to take revenge on their ex and hiring a hitman or a simple goon. From here they can "expand" for a second step. Perhaps they are surprised by the efficiency of a hired shark collecting the debt they were owed; the man realizes that it mustn't be limited to their personal funds, but perhaps he can use these services to recover debt owed to his ailing firm. Perhaps they failed to pay their hooker, who called on their organization who in turn threatened the man or demand a favour from him. Perhaps after the 7th-or-so purchase from the dealer, the dealer offers the man an interesting proposal to earn some dosh during his next trip abroad. Another category of "first contact" is when a character's interaction is "defensive", which can similarly lead to involvement in the underworld. A man threatened over and over by a loan shark finds no aid from corrupt law enforcement and thus hires a private contractor. An auditor of a large company uncovers a ridiculously extensive underground network in the company he is inspecting and is given a one-time-offer to "turn the other way". The second step here is a bit more complex; they may consider their options and find that they have no allies against the underworld other than the rivals of those that harass or assail them. The man with the loan-shark may find that his private contractor is a direct rival to the organization who originally loaned him, and they seek to reel him in. The auditor may realise the futility of his job and simply make use of his position to become part of the conspiracy. A last EDIT-note here; I do think the most common route people take for their first contact with the underworld is a route shaped by desperation.
