The Boystown neighborhood in Chicago, IL has a rich history as an LGBT enclave as reported by WBEZ: "in keeping with the 'criminal' treatment of homosexuality, most gay bars were run by the mob, since they had the power and bankroll to pay off the police and keep the bars open." In the 2015 book The Mafia and the Gays by Phillip Crawford Jr. is an entire chapter on the role of the Chicago Outfit in gay bars from the post-war years through the mid-1980s.
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Further reading that may be of interest: