Mike:
I've spoken to a lot of family members of mobsters up here in Chicago in the course of my own research, etc... on the Chicago Mob. So I have some experience in this area.
What I like to do if I sit down with people from that world whom I have not met before is to first set some very polite ground rules. Tell them that if there is anything or anyone they don't want to talk about, that you will avoid the subject. Refer to their relatives (obviously) with labels like "gambler" that are a bit more neutral than "hood" or "thug" or "mobster" or "crook".
This will make them feel more comfortable and what usually happens is they will voluntarily talk about the "sensitive" stuff if you let them raise it after assuring them you are in tune to their feelings.
Most of the people I've talked to (except the real BS'ers) are quite frank and honest about what their relatives were up to and interested in the subject. So they will talk to you about it if you just let them.
In terms of what questions to ask, organized crime like other crime is concerned with only one thing: increasing the wealth of the people involved. It just happens to be an illegal business, so you have to focus on some of the means to that end as well -- namely, political protection and violence.
So ask about the business aspects. What games did they run? Who were the owners of the place? How big was it, in terms of employees, weeekly "take", etc... What was gambling like in the area? More or less competitive, anyone could open up (with the OK of/payoffs to the politicians) or was there one syndicate that controlled everything? Who did they payoff? The police (as bagmen also for the politicians) or the pols directly? Ever get raided (even show raids)? Ever any violence in the place or problems with other gamblers/places? How did things change over time -- reform??
Hope this helps.
John Binder
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