The FBI long has been aware of allegations that the Mafia had infiltrated the entertainment industry, and according to a report dated December 11, 1959 one source "advised that many singers are subject to hoodlum control," and failure to play ball with the wise guys could be a career ender as Charlie Applewhite apparently learned:
Citing as an example of how hoodlum influence can destroy a singer, the informant referred to the case of CHARLIE APPLEWHITE. According to the informant, APPLEWHITE had a rapid rise as a singer and was very popular in both the night club and recording fields. Informant heard that APPLEWHITE refused to "knuckle under" to hoodlum control and subsequently disappeared from the show business scene, being no longer able to get night club bookings or recording dates. Informant added that APPLEWHITE has been completely destroyed as an entertainer and has had to seek other employment.
According to the same informant "most of the current popular singers, such as FRANK SINATRA, DEAN MARTIN, VIC DAMONE, etc., have many close hoodlum friends and it is generally believed that these friends have 'a piece' of the singer." In regard to Damone, "the informant advised that aside from being controlled by hoodlums, he is also heavily in debt to them due to the huge losses he has sustained at the gambling tables in Las Vegas."
A different informant advised the FBI on September 18, 1959 that Frank Sinatra "enjoys surrounding himself with hoodlums, and PCI advised that he believes that SINATRA would give up his show business prominence to be a hoodlum himself, if he had the courage to do so." The informant stated "that on the last day of SINATRA's appearance at the 500 Club" in Atlantic City, NJ during August 1959 he was accompanied by "Miami hoodlum, JOE FISCHETTI . . . as well as several other men of the same type who were unknown to him," and that in addition to the mobsters in Sinatra's suite at the Claridge Hotel he further "saw JIMMY McHUGH, the song writer, JACK ENTRATTER from Las Vegas, 'SKINNY' D'AMATO, owner of the 500 Club, and JACK LEONARD, the comedian." The informant "advised that it is common knowledge that FISCHETTI and SINATRA are close friends, and that SINATRA has a 'hoodlum complex.'" Indeed, Genovese capo Generoso Del Duca died in 1960 of a heart attack in the arms of Frank Sinatra after a night of clubbing in Miami, FL with the crooner and Fischetti.
Further reading that may be of interest: