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 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.

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CRITICISM–AND HUMOR–AS ENDANGERED SPECIES
In History, Humor, Politics, Social commentary on May 11, 2018 at 12:23 amWhat does it take for a White House correspondent to have his—or her—press credentials revoked?
According to President Donald Trump, it only takes writing a “negative” story about him.
On May 9—one year to the day since he fired FBI Director James Comey for refusing to offer a pledge of personal loyalty—Trump tweeted:
“The Fake News is working overtime. Just reported that, despite the tremendous success we are having with the economy & all things else, 91% of the Network News about me is negative (Fake). Why do we work so hard in working with the media when it is corrupt? Take away credentials?”
Donald Trump
And how did Trump reach the conclusion that “91% of” network newscasts on ABC, CBS and NBC focused on “negative” scandals and controversies?
By watching a segment of Fox and Friends on the Right-wing Fox News Network.
Assuming Trump carries out his threat, can an attempted Presidential crackdown on criticism of any kind be far behind?
Given the rampant and constantly demonstrated egomania of this President, probably not.
So, with the week coming to a close, here are some jokes that might soon find themselves on the endangered humor species list.
Why are Donald Trump’s supporters like Adam and Eve? They are naked, they have only one apple to eat, they live in a forest, and they think they’re in Paradise.
Donald Trump on Stormy Daniels: Version #1: I know NOTHING! Version #2: Gee, I guess I DO know something.
What’s the difference between John Gotti and Donald Trump? Some people actually loved John Gotti.
In President Donald Trump’s America, what is black and knocking at the door? The Future.
Donald Trump, watching the “Million Man March” on TV: “Now all we need is an auctioneer!”
A man knocks at the door of his neighbor’s apartment and shouts: “Quick, get up, get dressed.” From inside the apartment he hears screams of terror. “Don’t worry,” he says. “It’s nothing serious. I’m not with the Trump Police. I just want to tell you your flat is on fire.”
A group of friends gather in a house. Some of them start telling jokes about Donald Trump. One of the guests says, “Hey, it’s too noisy. I can’t hear the jokes. I’m writing it down, you know.” “How can you write down the jokes so fast?” asks a man. “Oh, I’m just writing down the initials.”
What’s the difference between Vladimir Putin and Donald Trump? Trump DIDN’T rig an election for Putin.
People ask, “Why does Donald Trump always suck up to Vladimir Putin? What’s he so afraid of?” Can anyone say “polonium”?
Let’s resolve the Stormy Daniels scandal the old-fashioned way: A heavyweight boxing match between Melania “The Slovenian Slugger” and Stormy “Come and Get It” Daniels. The loser gets to keep Trump. THAT should make it REALLY competitive.
What do American Fascists and Russian Communists have in common? Donald Trump.
What’s the difference between Germans and Trump supporters? Today’s Germans AREN’T Nazis.
The Trump “Sin-Eraser” Machine. Pick a sin you’re committed. Say, “I didn’t do it.” There! You didn’t do it!
Donald Trump’s next conspiracy theory: “Robert Mueller planted Rudi Giuliani on me to make me look like a stupid criminal.”
Melania Trump has unveiled her new campaign: “Be Best.” And not to be outdone, Donald has one: “Be Beast.”
It was a dark and Stormy night. Then Melania showed up with a carving knife—and all Hell broke loose.
Here’s how to make America great again in two easy steps: Step 1: Round up all Donald Trump supporters and put them on ships. Step 2: Sink the ships.
Donald Trump’s secret strategy to avoid impeachment: He’s going to blame it all on Eric.
Adolf Hitler had many faults, but at least he didn’t inflict his half-wit children on Germany.
What’s the difference between John Gotti and Donald Trump? John Gotti couldn’t fire the FBI director.
Think of Sarah Huckabee Sanders as Joseph Goebbels in a dress. Or, better yet, Hermann Goring.
REPORTER: “President Trump, you’ve been in the White house for 12 years now. Do you intend to seek a fourth term?” PRESIDENT DONALD TRUMP: “I’m not sure. That will be for the American people to decide.” Then Trump laughs for ten minutes.
What does Donald Trump think the Constitution is for? A substitute for toilet paper.
Trump HAS been a success if you know what MAGA really means: Make Adultery Great Again.
Donald Trump on Easter: “Jesus got a BIG resurrection when he met Mary Magdalene, but then he lost it three days later.”
It’s true that Donald Trump, Jr., met with a Russian lawyer in June, 2016. But there IS a perfectly good explanation for it. They were simply discussing how his father could adopt more foreign-born wives.
Poor Karen McDougal! If only things had gone right, SHE could NOW be the First Lady Trump cheated on.
Melania Trump is the sister that Natasha Fatale feels embarrassed to talk about.
How does every Donald Trump joke start? By looking over your shoulder.
Why do Trump supporters always travel in threes? One who can read, one who can write, and one to keep an eye on the two intellectuals.
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