What would be the best way to find out if a long dead family member may have been a mafioso? I’m useally good at researching things on the web, but I really have no clue as to where to start. And no I don’t know anyone in the mob to ask, heh. My family has had suppsiptions about this in-law for many years, and the ones who would know are either dead, or won’t talk about there business back then (1940ish). All I have is a couple names, so where should I start?
I’d tell you, but I’d have to kill you. 
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But seriously, Ladies and Germs . .
I would simply send inquiries to some of the mafia history websites out there, such as I think Gangland.com.
Also, check with your state’s crime commission. For instance in PA, our State Crime Commission released a report on organized crime in the state in 1990 that listed in details those suspected of being a part of the Life. The caveat is that your ancestor would have to have been convicted of a crime toi be listed.