FRANK SINATRA'S DARK SIDE

Rumours of Sinatra’s Mafia connections dogged his entire career and the legendary crooner certainly had connections to made men...

In 1950 the US Senate convened a high-profile committee to investigate the growing problem of organised crime in America. Popularly known as the Kefauver Committee, after its chairman Senator Estes Kefauver, its findings included admissions of the FBI’s failure to combat countrywide mob activity, leading to more than 70 local ‘crime commissions’ to combat the Mafia at local level, and a nationwide Racketeer Influenced and Corrupt Organisations Act. Unusually for the time, the proceedings were televised, with more than 30 million viewers eagerly tuning in to watch the testimonies of infamous gangsters: Mickey Cohen, Frank Costello, Jake ‘Greasy Thumb’ Guzik and others. Narrowly escaping a public grilling on this occasion was a struggling club singer called Frank Sinatra.

Council Joseph L Nellis questioned the singer in advance to determine his suitability for the stand, and the Kefauver Committee ultimately decided that no real purpose would be served by a Sinatra subpoena: his career was ailing at the time and the Committee generously opted not to finish him off by tarring him with the Mafia brush. However, during his questioning Sinatra nevertheless admitted to more than passing acquaintances with a significant list of made men: Lucky Luciano, Bugsy Siegel, Willie Moretti and Al Capone’s cousins, The Fischetti Brothers.

Sinatra would not escape similar hearings in the future. While he always denied any Mafia involvement, his name kept cropping up. He was called before a Joint Senate-House Select Committee on Crime – along with his fellow Rat Pack performer Sammy Davis Jr – investigating gambling and corruption related to sport, in 1972. There was further public testimony, and further denials, in the hearings of the Nevada Gaming Control Board in 1981, where Sinatra was seeking to obtain a lucrative gambling license for his Las Vegas interests. They were never proven, but the whispers of Sinatra’s intimate links to the mob were never silenced either. Was he really part of the Mafia? Or was he, as many have concluded, just a ‘groupie’, in love with the life but content to watch from the sidelines?

Possible Mafia ties stretch back to Sinatra’s grandfather’s youth in Sicily, the Italian island that was the birthplace of the Cosa Nostra. Frank’s grandfather, Francesco Sinatra, was born in 1857 in the hill town of Lercara Friddi: Mafia heartland only about 25 kilometres (15 miles) from the famous town of Corleone. While there’s no evidence that Francesco was involved in any dubious undertakings, he lived on the same street as the Luciano family, whose most famous son Salvatore – nicknamed Lucky – would come to be considered one of the fathers of organised crime in New York in years to come. Lucky’s address book even contained the name of one of Francesco’s in-laws, so it’s entirely possible that Francesco and the Lucianos were personally acquainted.

Francesco Sinatra emigrated to New York in 1900 with his wife and five children. The young Antonino, Frank’s father, became an apprentice shoemaker, but also worked as a chauffeur and a professional bantamweight boxer. He had run-ins with the law involving a hit-and-run accident – for which he narrowly escaped a manslaughter conviction – and for receiving stolen goods. He married Frank’s mother Dolly in 1913, and Frank himself was born, an only child, two years later.

Dolly was a midwife, known to some as Hatpin Dolly due to her notoriety for performing illegal backstreet abortions, for which she was convicted twice. But she was also heavily involved in local Hoboken and Jersey City politics, working for two successive mayors at a time when the boroughs were infamous for corruption. When she and Antonino opened a bar in 1917, she became well known for bouncing drunks on the streets with her ever-present billy club.

The bar was the environment in which the young Frank Sinatra grew up, at a time when selling alcohol was illegal thanks to USA’s Prohibition laws and, specifically, the Volstead Act. Frank would be doing his homework in the evenings in the corner of an establishment that could only remain in business thanks to his father’s bootlegging activities with the local gangster Waxey Gordon, who in turn was connected to Lucky Luciano. Hoboken, as a port town, was a major transit point for illicit alcohol shipments and Frank’s uncles, Dolly’s brothers, were also heavily embroiled in the trade. Prohibition, perversely, was big business if you were on the wrong side of the law. It was the making of the Mafia in the United States. Frank’s upbringing certainly wasn’t wracked with hardship: his family rode out the Great Depression of the 1930s to the extent that Dolly bought him a brand-new car for his 15th birthday.

Despite his constant exposure to mob activities, Frank seized on a different ‘racket’ very early in life. He gave his first public performances singing along to the player piano in the Sinatra Bar and Grill, at the age of about eight.

His first professional break as a singer came in 1935 when he was 20, as a member of local singing group The Hoboken Four (a trio until Dolly leaned on them to let Frank join). This led to years of singing in clubs and bars in New York and around the country: an occupation in which fraternising with mobsters and their bosses would have been unavoidable. Organised crime went hand-in-hand with the bar business, and even after Prohibition ended, the mob remained silent partners in many businesses. They were also heavily involved in the music industry, controlling most jukeboxes nationwide, an therefore largely dictated what records would be most successful.

“Saloons are not run by the Christian Brotherhood”, Sinatra hedged in later life. “A lot of guys were around that had come out of Prohibition and ran pretty good saloons. I worked in places that were open. They paid. They came backstage. They said hello. They offered you a drink. If Saint Francis of Assisi was a singer and worked in saloons he’d have met the same guys. That doesn’t make him part of something...”

Sinatra enjoyed a very good year in 1939 – he had a contract with bandleader Tommy Dorsey, a hot enough act for Sinatra’s national profile to be hugely increased. In his first year with Dorsey, Sinatra recorded more than 40 songs and topped the charts for two solid months with I’ll Never Smile Again. But Sinatra’s relationship with Dorsey was a troubled one, and their parting in 1942 began the first public rumblings of Sinatra’s possible Mafia connections.

With his profile on the increase, Sinatra was keen to go solo, but Dorsey refused to release him from a contract that had years to run. This put Frank in a difficult position; he was being wellpaid but his career was not his own. If he broke his contract he would owe considerable chunks of his income to Dorsey for the next decade: a clause Sinatra found unsavoury. Lawyers desperately searched in vain for loopholes in the deal that would allow Sinatra to walk free, and it looked like Dorsey would keep his biggest star. However, he was quickly persuaded to change his mind. Sinatra denied it, but Dorsey claimed that he was visited by Willie Moretti and two sharp-suited henchmen. “Willie fingered a gun and told me he was glad to hear I was letting Frank out of our deal”, Dorsey recalled. “I took the hint.”

The young crooner made the most of his opportunity and the next few years saw ‘Sinatramania’ grip the US, as the singer recorded hit after hit. There was also resentment, though, as during World War II, he somehow managed to avoid military service. Rumours were rife that he had paid his way out – although the FBI never found any evidence of this – while other sources suggest he was deemed unfit on psychological grounds and because of a perforated eardrum. Whatever the reason, pictures of him at home, cigarette in one hand and drink in the other, surrounded by beautiful women and living the superstar lifestyle, did not endear him to those in uniform and their families.

However, that controversy was a drop in the ocean compared to the furore that erupted when Sinatra was photographed in Cuba in 1947 at a mob celebration for Lucky Luciano’s release from jail. The incriminating pictures showed Sinatra with his arm around Luciano on a hotel balcony; with Luciano at a Havana nightclub; and with the Fischetti Brothers at the airport, disembarking a plane with a case in hand. Why would he have carried his own luggage? Comedian and movie star Jerry Lewis (former partner of Rat Pack lieutenant Dean Martin) alleged that Sinatra carried money for the mob. Sinatra claimed that the case was full of art supplies, and that he couldn’t have physically carried the $2 million he was accused of trafficking in the case. Journalist Norman Mailer quickly established that much more than $2m fits easily in an attaché, effectively debunking Old Blue Eyes’ argument.

If there was any doubt about what was in the case, Sinatra’s presence at the mob shindig was inarguable. Sinatra was close to Joe Fiscetti, who was a talent agent for mob-owned clubs all over the US, and had agreed to the impromptu Havana trip while holidaying with his wife Nancy across the water in Miami. Once in Cuba, Sinatra claimed, he learned the embarrassing truth that he was ensconced at a Mafia convention, and reasoned it would be impolite – not to say dangerous – to make excuses and leave. He stayed and performed for the goodfellas, but witnesses confirmed that he displayed little reserve in accepting the mob’s hospitality, which included hotel-room orgies with ‘planeloads’ of call girls. It was as if Sinatra felt right at home, and many of his Havana acquaintances would remain with him during his later Las Vegas years.

Before the glittering lights of Vegas and the Rat Pack years, though, came the doldrums, as Sinatra’s star waned in the US, outshone by younger up-and-comers like teen heartthrob Eddie Fisher. Sinatra, now in his thirties, failed to launch a successful television career, and attempted suicide in 1951.

But he achieved one of the greatest comebacks ever when he landed a role in the 1953 movie From Here To Eternity, for which he won an Oscar for Best Supporting Actor for playing Angelo Maggio, a down on his luck Italo-American GI. Once again, evidence suggests he didn’t achieve that success entirely on merit. The head of Columbia Studios, Harry Cohn, had been adamant that Sinatra would not be cast, until a phone call from gangster Johnny Roselli persuaded him otherwise. The alleged episode was the inspiration for Mario Puzo in his novel The Godfather, in which studio head Jack Woltz is terrorised into casting Johnny Fontane in his movie with a horse’s head left in his bed. Roselli’s display of power was less overt but, it seems, just as impactful. Having helped Sinatra revive his career, the mob weren’t going to let him out of their clutches. FBI director J Edgar Hoover famously described Sinatra as having a “hoodlum complex”, and he clearly relished the dark glamour of gangsters and criminals. The reality though was that he was as much in thrall to the Mafia as he would have been to Tommy Dorsey if he’d failed to break his contract. When they asked him for free performances he would jump to oblige, and in 1953 when Mafia fortunes were invested in making Las Vegas the gambling capital of the world, Sinatra was key. Sinatra was to be a regular fixture at the mob-run Sands Hotel and Casino, in return for a two per cent stake. This was big business.

The Sands became his home away from home until the late-1960s, and in the mid-1970s another incriminating photograph would haunt him through the media: he was snapped backstage at the mob-built Westchester Premier Theatre in New York, with his arm around crime boss Carlo Gambino. The FBI kept a file open on Sinatra for five decades until his death in 1998.

Sinatra dressed like a gangster, talked like a gangster, grew up around gangsters and fraternised with gangsters. Perhaps the greatest irony is that he was never actually a made man. His relationship with the mob was clearly beneficial to both sides: Sinatra got fame and fortune and the mob had a tame star who could be used to boost coffers and shore up investments when necessary. If Sinatra was instrumental in establishing Las Vegas, Las Vegas was equally important in his 1950s comeback, but while the singer was clearly starstruck by the mob, it’s unclear whether the mob was similarly dazzled, or simply saw Sinatra as expedient as long as he behaved. “I’d rather be a don for the Mafia than president of the United States,” is a quote often attributed to the singer. If that’s true, it seems that he never really got His Way after all.

JFK: Sinatra’s crush

John F Kennedy and Frank Sinatra first met at a Democratic Party rally in 1955. They immediately hit it off and became firm friends both on the golf course and in the hostelries of society nightlife, where Sinatra was known to occasionally set Kennedy up with some extra-marital female companionship.

Sinatra was even involved in Kennedy’s run for the US presidency, and as always, the Mafia weren’t far from the story. Kennedy’s father Joseph was afraid to use his own Mafia links to help his son’s campaign, so allegedly asked John’s new best friend to be an intermediary. Sinatra was more than happy to oblige, so he helped to convince mob boss Sam Giancana to employ ‘persuasive methods’ to deliver Illinois and West Virginia to Kennedy’s cause in the Democratic primaries before the election.

The plan paid off, but once JFK was president he soon began to distance himself from Sinatra, realising that it would be unwise for a president to risk mob scandal. The final straw for Sinatra was when Kennedy snubbed him at his Palm Springs home, opting to stay with Bing Crosby instead. The bitter Sinatra, who had invested in lavish decorations and a helipad specifically for the visit, was so upset that he went around his house smashing his treasured Kennedy souvenirs with an axe. A long-standing Democrat, Sinatra switched his allegiance to the Republicans in later years.

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SINATRA’S RAP SHEET

Crime: Street Fights

Sinatra was a skinny child known for his singing and his closeness to his mother, but he claimed in later life that he saw plenty of delinquent juvenile action. His teeth, he said, were straightened not by a dentist but in a punch-up, and the scar above his nose was from a Coke bottle smashed in his face.

Verdict? Sinatra fed the experiences into his personal mythology: a tough kid who grew up on the mean streets.

Crime: Bootlegging

The Sinatras ran a bar during Prohibition, so naturally there was plenty of illegal activity keeping them in business. Frank grew up among gangsters and bootleggers. It’s hard to imagine that Frank, right in the middle of it all, didn’t help out his father and uncles with liquor runs on at least some occasions.

Verdict? His family had run-ins with the law, but Frank was never implicated and the bar business remained a roaring success.

Crime: Adultery

In 1938, before Sinatra became famous, he was caught in a compromising position with a married woman – never publicly identified – in north New Jersey. This might not seem very surprising given his reputation as a womaniser, but back then adultery was illegal, so it was a serious business.

Verdict? He escaped a $500 fine when the charges were dropped, but still had to pose for a mugshot.

Crime: Dodging the draft

Sinatra avoided having to join the US armed forces during the Second World War, and a persistent rumour suggested that he’d paid a $40,000 bribe to doctors in New Jersey to be declared unfit for service. While his peers went and fought for the Allies in Europe and Asia, he remained at home living the decadent high life of a superstar.

Verdict? FBI files released in 1998 revealed that Sinatra had been legitimately rejected due to a perforated eardrum and ‘mental instability’, but the myth still prevails among some.

Crime: Assault

In 1947, while having dinner at Ciro’s in Los Angeles, Sinatra allegedly punched newspaper columnist Lee Mortimer. It was reported at the time that, as Sinatra walked past his table, Mortimer made a reference to his Italian ancestry and his links with the Mafia, receiving a punch on the jaw for his troubles.

Verdict? Sinatra had to go to court where he pleaded not guilty and was released on bail. The charges were dropped before the trial when, it was reported, Sinatra paid $9,000 to settle. Rumours of him using his fists to end disputes followed him throughout his career.

The Rat Pack

The name ‘Rat Pack’ was first given to a group of New York celebrities in the 1950s centred around Humphrey Bogart, later appended to the peer group around Frank Sinatra. The group never referred to themselves by that moniker, preferring the Summit or the Clan. They played together on stage and on film for years, usually crashing one another’s gigs rather than performing as a formal group.

1. Frank Sinatra, singer/actor

Greatest hits: My Way, Strangers in the Night, It was a Very Good Year, I’ve Got You Under My Skin, The Lady Is a Tramp, Fly Me To the Moon, New York New York

Worst moment: Attempted suicide in 1951.

Did you know? He was replaced by Clint Eastwood in Dirty Harry after an injury forced him to pull out, and turned down Charles Bronson’s role in Death Wish.

2. Dean Martin, singer/actor

Greatest hits: Everybody Loves Somebody, Memories Are Made of This, That’s Amore, You Belong To Me, Ain’t That a Kick in the Head?

Worst moment: Walking off the Together Again tour in 1988, leading to a late-life estrangement from Sinatra. Martin didn’t like playing stadiums.

Did you know? Drunkenness was part of the reputation he cultivated, but the ‘booze’ he drank on stage was often nothing more than apple juice.

3. Sammy Davis Jr, singer/dancer/actor

Greatest hits: What Kind of Fool Am I?, Candy Man, I’ve Gotta Be Me

Worst moment: The car accident that injured him and cost him an eye in 1954.

Did you know? Davis was a significant financial supporter of the American Civil Rights movement, but suffered racist jokes and bullying from his Rat Pack colleagues.

4. Joey Bishop, actor/comedian

Greatest hits: The Thin Man (TV), Easter Parade, Ocean’s Eleven (film)

Worst moment: His 1960s talk show The Joey Bishop Show lasted only two years, battered in the ratings by Johnny Carson’s famous Tonight Show.

Did you know? Bishop was the last surviving member of the Rat Pack; he died in 2007.

5. Peter Lawford, actor/producer

Greatest hits: The Thin Man (TV), Easter Parade, Ocean’s Eleven (film)

Worst moment: Falling out with Sinatra in 1963, as Sinatra believed he had failed to intercede using his family connections when Kennedy opted not to stay at Sinatra’s house. Lawford never worked with the Rat Pack again.

Did you know? Lawford married Patricia Kennedy, making him John F Kennedy’s brother-in-law.


In "All About History Annual Volume 2, 2015" UK, excerpts pp. 145-149. Adapted and illustrated to be posted by Leopoldo Costa.

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