As I mentioned around the end of Peaky Blinders, there have been dedicated RPGs for this at least as far back as GangBusters first edition in 1982 which had rules for playing both sides, as well as reporters and private eyes.
Of course the main 20s-30s RPG has always been Call Of Cthulhu but it doesn’t cover this side of the era, and most others are pulps like Adventure!
Non-SFF-ish gangster gaming is more common with miniature skirmish wargames. Like one called The Chicago Way...
(One thing I would have for this is vehicles, having quite a few Lledo Days Gone toy cars which are about 25mm scale. One of these days I’ll actually do something with them.)
And the main Chicago-centric RPG is Vampire: The Masquerade where Capone was one of the city’s NPCs, so I’ve inevitably thought of doing Prohibition-era Vampire as well, with the gangster side being an obvious connection - I made a fake trailer for one using footage from Boardwalk Empire - but a Great Gatsby style high life game could work too.
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