I like the Italian Mafia Concept Old Dude, however you are behind the times
It's all about the Russian and Albanian Mafias. The US jails do not scare them, and they eat FBI agents for breakfast. I miss the Jamaican Mafia and the reggae, but Steven Segal killed Screwface and they have never been the same.
The prison part is sweet. Did I mention I have worked with Inmates and Court mandated clients? Anyone who needs a prison shrink just let me know!
Oh, and I want to upgrade the Tommy Guns and cheap .38's to these: