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Raise a Floppa - The Loop
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Bobby is, presumably, a member of the Sindacco Family, a cosa nostra mob family. Bobby lives on the East coast of the United States of America, which could be Liberty City, Carcer City or Vice City. It is mentioned by two members of the Sindacco family that he had recently become an open homosexual.
He and Lance Urwell are the only known members of the Sindacco family to still be alive.