Part the Second:
Consider the Gentleman Cracksman
While playing Call of Cthulhu and other RPGs, not only will your adventures/investigators encounter criminals, they may actually have one or more of them in their party. Although not an Apache, a highly notable gentleman criminal, Maurice Leblanc’s Arsène Lupin was an early antihero from the teens and 20s. Having a highly moral master criminal in your investigation group would be an asset, as long as he/she stays out of jail.
They have many useful skills beyond the obvious lock picking, burgling, pick pocketing and the like. They will have good contacts, well place confederates, know how to get information and has a good knowledge of items to sell or buy. If your gentleman criminal deals in stolen art or artifacts, that might make a good hook for the character and a reason to join the group. The downside is if your gentleman criminal adventurer is well known or has detectives actively seeking him, you may have a lot of problems. It can be compounded if both criminal organizations and police are seeking him and anybody associated with him. Game masters should use this as a judicious balance for allowing an ultra-talented player character in the group. Be careful with such characters as they can run away with the group, leaving little for everybody else.
Some books about Arsène Lupin are available through Project Gutenberg as free downloads:
You can further research the Victorian/Edwardian genre of gentlemen criminals by reading up on Raffles, The Amateur Cracksman by E. W. Hormung whose works are also available on Project Gutenberg.
A critique of Raffles and the metamorphosis & moral ambiguity of Raffles and such characters can be found in an essay by George Orwell.
Two additional books I can recommend about gangs in major cities is The Anti Society about Victorian crime and slums in London, and the sweeping overview of gang activity of Victorian and later gangs in the 1928 Gangs of New York (later made into a movie) and The Anti-Society: An Account of the Victorian Underworld by Kellow Chesney, 1970. I highly recommend both books.
Although I haven’t read it yet, you might try George Orwell’s (of 1984 fame) Down and Out in Paris and London, which although fiction, is based heavily on his time as a penniless writer in those two great European metropolises. I might also suggest Frederich Engels who wrote extensively about poverty in England in his 1845 book, The Condition of the Working Class in England. Despite being the co-creator of what we know as Marxism (with Karl Marx), his early book still makes good reading and first-hand account journalism. Dickens is another good source of pre and early Victorian information slum living such as Oliver Twist.
Other sources for antihero characters of the 20s and 30s might be Chandu the Magician and Mr Moto, their motives can be obscure, they methods questionable, but they have a bias towards an self-internal law, that vaguely meshes closer to good than evil. I won’t go into Doc Savage, who wasn’t an antihero, but he did lobotomize criminals against their will. The difficulty is not letting them do all the work or become a danger to the group and the mission.
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