Sean Penn is not the first celebrity to “get close to” a gangster.

Singer Frank Sinatra set the standard as far back as the 1940s when he was often seen in the company of notorious Mafiosi such as Charles “Lucky” Luciano and Willie Moretti.

(It was Moretti who is rumored to have freed Sinatra from his financially-limiting contract with bandleader Tommy Dorsey in the early 1940s.  

His alleged method of persuasion: Jamming a pistol down Dorsey’s throat and threatening to kill him. Dorsey eventually sold the contract to Sinatra for one dollar.)

But the mobster whom Sinatra was most-often linked with—by gossip and FBI reports—was Sam “Mooney” Giancana.

Giancana started out as a “wheelman” and enforcer for the teenage “42 Gang,” then joined the Chicago mob in the late 1930s. By 1957 he had been appointed its boss.

Sam Giancana

Sinatra often partied with Giancana, both in nightclubs and at his own residence in Palm Springs, California.

In December, 1959, financier Joseph P. Kennedy summoned Sinatra to the family compound in Hyannis Port, Massachusetts. His son, Senator John F. Kennedy, was planning to run for President in 1960. And the elder Kennedy wanted Sinatra’s help.

Sinatra and the Senator were by now well-acquainted. They shared a taste for gossip, nightclubs and beautiful women.

According to Sinatra’s daughter, Tina, the Kennedy patriarch said: “I think that you can help [the campaign] in [the] West Virginia [primary] and Illinois [in the general election] with our friends.

“You understand, Frank, I can’t go. They’re my friends, too, but I can’t approach them.  But you can.”

Frank Sinatra

By “our friends,” Kennedy meant the Mafia. Joseph P. Kennedy had done business with the mob as a bootlegger during Prohibition.

Now he wanted the Mafia to pressure local union members into voting for JFK—and making contributions to the Kennedy Presidential campaign.

Sinatra went to his friend, Sam Giancana, and asked for the mob’s support.  And Giancana promised to deliver it.

In return, Giancana—and other mobsters—expected to win an ally in the White House. He was later overheard on an FBI wiretap saying he had been promised by Sinatra that “if I even got a traffic ticket, none of those fuckers [the FBI] would know me.”

Since 1959, Giancana and other “Top Hoodlum” mobsters had been under increasingly heavy FBI surveillance. Giancana wanted it stopped.

And Sinatra had assured him that, under a Kennedy Presidency, it would stop.

On Election Night, 1960, John F. Kennedy carried Illinois—and won the White House by a mere 120,000 votes nationwide.

Then, to the horror of the Mafia, JFK installed his brother, Robert Francis Kennedy, as Attorney General. From 1957 to 1959, RFK had pursued gangsters as chief counsel for the Senate Rackets Committee. 

Now he declared all-out war on organized crime.  Convictions against organized crime figures rose 800% during his four years in office.

 Robert F. Kennedy

Sinatra tried to deliver for Giancana.  He sent Peter Lawford—his Rat Pack pal and brother-in-law to the President—to talk with Robert Kennedy about laying off on the Mafia don.

Kennedy bluntly told Lawford to mind his own business.

Giancana came under even greater pressure. FBI agents put a 24-hour “lockstep” surveillance on him, following him even into church and restrooms.

“I was on the road with this broad,” Giancana raged to his murderous associate, Johnny Formosa. “There must have been 20 guys [FBI agents]. They were next door, upstairs, downstairs, surrounded all the way around!

“Get in a car, somebody picks you up  I lose that tail—boom!—I get picked up someplace else!  Four or five cars, back and forth, back and forth.”

In another exchange with Formosa, Giancana’s anger at Sinatra boiled over:

“The last time I talked to [Sinatra] was at the hotel in Florida.  And he said, ‘Don’t worry about it.  If I can’t talk to the old man [Joseph P. Kennedy] I’m going to talk to the man [President Kennedy].’

“One minute he says he’s talked to Robert, and the next minute he says he hasn’t talked to him.  So he never did talk to him.”

Formosa suggested a remedy: “Let’s show ’em.  Let’s show those fuckin’ Hollywood fruitcakes that they can’t get away with it as if nothin’s happened.

“Let’s hit Sinatra. Or I could whack out a couple of those other guys, Lawford and that [Dean] Martin.  And I could take the nigger [Sammy Davis, Jr.] and put his other eye out.”

Giancana refused to issue the contract. But he seriously considered doing so, as he confessed to a Chicago associate named Tommy DiBella:

“One night I’m fucking Phyllis [McGuire, a member of the famous McGuire sisters trio], playing Sinatra songs in the background, and the whole time I’m thinking to myself, ‘Christ, how can I silence that voice?’

“It’s the most beautiful voice in the world. Frank’s lucky he’s got it.  It saved his life.”

Sinatra’s Rat Pack “pally,” Dean Martin, summed it up: “Only Frank could get away with the shit he’s got away with. Only Frank. Anybody else would’ve been dead.”

Sinatra survived the murderous anger of a mob boss.  It remains to be seen if Sean Penn can do the same.