I think it would be interesting to read about his involvement with the rackets. You could interview him to jog his memory and ask him to write about it. Also I know reddit's IAMA subreddit loves topics like these.
I don't know how interesting it all is. He basically showed up in the Combat Zone one day and went from place to place telling them they were going to start paying him. The guy they were already paying got disappeared, so they complied.
Over time the territory came to include Chinatown (which abuts the Combat Zone), and he eventually got hooked up with the non-Irish mob in Providence (where I guess he was one of their better earners). He also apparently stole a lot of boats (very easy to steal, very hard to track), which when I found out helped explain to me why my grandmother was Admiral of the Quincy Yacht Club without ever owning a boat.
The FBI issued an arrest warrant for him the day I was born, so he fled (apparently to California). They seized all my mom's assets (in an effort to get her to cooperate), and tailed her and I everywhere for most of my childhood.
He ended up getting arrested back in Boston in the early 90's (A few years ago I worked at the same company as the prosecutor who tried his case, which we both discovered one night drinking at a company off-site...awkward conversation).
From what I know, he's now living in Southern California (he had a security consulting company...which I suppose it somewhat serendipitous considering that both my brother and I ended up working in information security).
I'm not one of those people who believes that people are "good" or "evil", but if forced to decide one way or the other, my dad falls pretty squarely into the "bad" camp. The thought of him participating in an IAMA on Reddit is about the funniest thing I can think of.