The "Chairman" was connected to Sam Giancana and Johnny Roselli. Roselli was from Cleveland and was associated with a small time hood by the name of Jimmy "The Weasel" Fratianne, who wrote a book by the same name.

In this book he describes how he and Roselli would set up phony charity benefit dinners and shows and have Sinatra and friends come perform then they would abscond with the funds. It was a scam they played for years. Did Frank know the truth? according to The Weasel...Sinatra just believed he was helping people. Kinda of a 'don't ask , don't tell" arraingment.