The Chairman of the Board (Frank Sinatra) paid Mob dues.

I remember an old TV interview with the actor Michael Cain  where the interviewer asked Mr Cain what it was like to be rich and famous. Mr Cain thought for a minute and then responded with:

" It's great. It would be even better if I was just rich."

I think what Mr Cain was saying is that fame can make you rich, but it comes at a price, a loss of privacy is one and a target for rumor and innuendo another. 

This article appeared on the Business Insider Australia website and was authored by Michael Kelley Nov 22, 2013.
The “Rat Pack” from left to right: Frank Sinatra, Dean Martin, Sammy Davis Jr., Peter Lawford and Joey Bishop
The article presents an odd occurrence in Frank Sinatra's career when he and his "Rat Pack" cohorts (all big stars at the time) played a small, out of the way, night club/ restaurant by the name of  "Villa Venice" situated  in Chicago, Illinois USA.

Note: Peter Lawford ( a longtime member of the Rat Pack) who was married to one JFK's sister's, did not participate in this event.


Villa Venice club, Chicago
Sam Giancana Chicago Mob boss
Sam Giancana Chicago Mob boss
The club was said to have mob connections, particularly to the Chicago mobster Sam Giancana.

This particular conspiracy theory has shared character's and close ties to the JFK  and RFK Mob assassination  theories. Not an unusual occurrence with the more complex conspiracy theories, which often interact with other theories and at times they can even absorb each other.


The Mafia detested the administration of John F. Kennedy as Attorney General Robert F. Kennedy raised the number of mob convictions from 35 in 1960 to 288 in 1963.

The Kennedy brothers, John F. Kennedy, left, Robert Kennedy, and Ted Kennedy, right, in Hyannis Port, Massachusetts.

But there may be a much deeper connection between the Kennedys and the mob, and legendary entertainer Frank Sinatra reportedly served as a key intermediary and whipping boy in one case.

According to “The Dark Side of Camelot” by Seymour Hersh, Joseph P. Kennedy, Sr. (JFK’s father) set up a meeting with Chicago mob boss Sam Giancana to obtain Giancana’s support for Jack Kennedy’s run for the White House — thereby combining the sway of Chicago crime syndicate with that of Mayor Richard J. Daley’s Democratic machine.

Richard J. Daley Mayor of Chicago at the time of JFK’s primary.

Hersh also reported, along with others, that Giancana also helped funnel cash to buy votes and endorsements for the West Virginia Democratic primary election in May 1960.

Professor Larry Sabato author of “The Kennedy Half-Century: The Presidency, Assassination, and Lasting Legacy of John F. Kennedy”

The new book “The Kennedy Half-Century: The Presidency, Assassination, and Lasting Legacy of John F. Kennedy” by University of Virginia professor Larry Sabato highlights the connection by citing the story that Joseph Kennedy asked for Giancana’s help over a dispute with another mobster, Frank Costello, and offered “the president’s ear” in return.

Frank Costello mob boss

Sabato also writes that “when JFK began having an affair with a black-haired beauty named Judith Campbell while he was still a U.S. senator, Giancana slept with her as well, reportedly so that he would eventually have a direct link to the White House.”

Judith Campbell Exner mistress to both JFK and Giancana
Judith Campbell Exner mistress to both JFK and Giancana

It turns out, according to Sabato, that Sinatra introduced Senator Kennedy to Judy Campbell and also “served as the go-between for the West Virginia primary shenanigans.”

After JFK reached the White House, however, the mob boss was not welcome near the president’s ear. And Sinatra was the one that ultimately paid for it.

When the Kennedys turned on Giancana once they were in the White House, Sinatra had to work hard to deflect the mobster’s wrath at Sinatra on account of the Kennedys’ unfaithfulness. In atonement, the singer played at Giancana’s club, the Villa Venice, with his “Rat Pack” of fellow entertainers, for eight nights in a row.

Sabato notes that “Sinatra worked his way back into Giancana’s good graces, but the Kennedys never did.”

It is odd that stars of the calibre of the Rat Pack would play for such a length of time at such a little venue. But, they all managed to boost their individual profiles and careers, as well as make a lot of money out of it. The "Rat Pack" even released a live recording of the event, that is still selling well today. With this in mind the event  may not have been anything more than a clever marketing exercise that benefited all at the time. Or it may have been Frank paying his Mob dues...


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