Herbie was a Chicago guy who grew up near Melrose Park and started working with Lombardo and Tony Spilotro under Phil Alderisio. Herbie started building a large loanshark operation, aided largely by Phil's crew who pushed clients his way. What I've hear is that poor Herbie went to prison in the 1960s and when he came out, his racket had been taken over. He was also being investigated for a murder in Chicago and thus there wasn't much point sticking around.

So he went to Vegas to follow Spilotro, who had been made while Herbie was in jail and ran Spilotro's loanshark books.

I'm sure Herbie knew the Milano's, but he had deeper and higher connections in Chicago. He was with the Grand Avenue crew and probably was still sending them a cut all the way up until he was killed.