How well off did the kids, grandkids and even great grandkids of the top bosses end up being after years of them being retired or dead? Bosses such as the namesakes of the 5 families. Are there cases of any of their kids or grandkids struggling financially since they have been gone? A big thing for them when they were bosses was the idea of generational wealth. Á la Michael Corleone in godfather 3 how he put an emphasis on the importance of his family and making his business completely legitimate.

Its a case by case issue. I definitely can't think of a boss' family who is hurting.

In a 2013 post is said that the Ray Patriarca sr grandson had a parking lot and the people pay for make a photo with him,not a milionaire so.

Tommy Gambino is very wealthy. Gigante’s family as well but maybe not like Gambino’s. Joe Profaci and his family are still well off I believe. I am not too sure about Genovese’s.

People talk about the construction racket the mob had like it was a real gold mine. Some would lead you to believe that it was more profitable than drugs the way that they talk about the mob having to approve every drop of concrete being laid. I would think that the construction tycoons in the mafia have succeeded in generational wealth for their families for years to come.