5 December 2015updated 01 Apr 2023 5:45pm

Sinatra and the mob

Just what was Frank Sinatra's association with "made men"?

At some point in the early 1980s, Pablo Escobar built a private zoo. The Colombian drug baron had yet to embark on his campaign of assassinations and bombings that soon terrorised his country, leaving a trail of dead politicians, judges and police in its wake. Business was good. Profits were up. Less than a decade into his career as el Zar de la cocaína, Escobar had cars, planes, sports fields, houses, lakes, farms, all the fine food and drink he could need. An African hippopotamus? Why not? Send one to the ranch – no, make that four. As a local fisherman later said, anything could happen at “the whim of [the] villain”.

Anything, it seems, including an audience with Frank Sinatra. In 1983 Escobar took members of his extended family on a trip to the United States. After queuing for rides at Disney World in Florida and taking a tour of the FBI building in Washington, DC, they embarked on a 760-mile pilgrimage to Graceland, Elvis Presley’s house in Memphis. The wives and children were then sent home and the men went to Las Vegas, gambling their way through $1m of walking-around money and staying at the Caesar’s Palace casino. It was there that the Escobars, masquerading as a group of “important real-estate investors”, were introduced to the headline entertainment.

“We had dinner one night with Sinatra,” recalled Roberto Escobar, Pablo’s brother, who was so thrilled to meet the singer that he “had goose bumps”. “During dinner, Pablo told Sinatra that we were going to make a helicopter tour the next day and Sinatra asked to come with us . . . Frank Sinatra became our guide as we spent about an hour and a half flying all over the area. ‘This is the Colorado River, this is the Grand Canyon.’ He showed us all the scenery.”

Sinatra, it turned out, had been unaware of his new friends’ true identities. A few years later, when Pablo Escobar had become an internationally wanted super-criminal whose cartel was bringing in more than $60m a day (in 1989 Forbes reported that he was worth $3bn), the acquaintance who had introduced them at Caesar’s Palace received a phone call. It was the singer. “I’ve been watching TV,” he said, alarmed and probably pissed off. “Is that Pablo Escobar the guy we met in Las Vegas?”

It was an innocent encounter but one that was in keeping with Sinatra’s lifelong fascination with criminals. He was born in 1915 into a family of Italian-American immigrants who lived in Guinea Town, a cobblestone district of New Jersey populated almost entirely by fellow expatriate countrymen. His parents – Marty, a boxer-turned-fireman, and Dolly, nominally a midwife but also a “facilitator” in the community who carried out illegal abortions and organised for the Democratic Party – owned a boozy tavern during Prohibition. Dolly’s brother Lawrence was rumoured to have been a whiskey hijacker for the bootlegger Dutch Schultz and, it’s said, Bugsy Siegel, Meyer Lansky, Willie Moretti, Frank Costello and Lucky Luciano – a who’s who of the era’s mafiosi – passed through or operated in the neighbourhood. Maybe some of them stopped at Marty’s and Dolly’s bar for a drink.

Frank Sinatra’s involvement with gangsters was a complicated one. The myth, as popularised by Mario Puzo in his novel The Godfather (and Francis Ford Coppola’s 1972 film adaptation), is that the singer was simply a ring-kissing beneficiary of the Cosa Nostra. In Puzo’s rather dubious fictionalised account, both Sinatra’s contract-breaking departure from Tommy Dorsey’s orchestra in 1942 and his selection for his Oscar-winning acting role in From Here to Eternity (1953) were direct results of a capo dei capi’s interventions.

Yet, although it’s true that the singer associated freely with “made men”, his entanglement with them seems to have been based more on mutual curiosity than a client-padrone relationship. At a time when Italians in the United States were still despised as ethnic outsiders, the lawless, gun-wielding enforcers of Old-World “justice” must have appealed to the young Sinatra, just as, later in his career, his unparalleled status as the world’s best-known Italian American – if not quite the world’s best-known American – must have won him the respect of the uomini di rispetto.

And it seems that he made himself useful to crooks, regardless of whether or not they were Italian. In Sinatra: the Chairman (newly published by Sphere), James Kaplan details the singer’s arrangements with gangsters such as Joseph “Doc” Stacher, a Jewish syndicate leader who allegedly “fronted Frank $54,000” to buy points in the Sands casino in Las Vegas. Sinatra’s relatively clean criminal record and his drawing power as an entertainer made him a perfect fit as a frontman for the business – the gambling town was run more or less openly by mobsters, but appearances had to be kept up.

In 1960, Sinatra and a group of associates applied to buy a majority stake in Cal-Neva, a resort and casino that straddled the border between California and Nevada. This time, the singer, according to Kaplan, was “fronting for Sam Giancana” – the Sicilian-American leader of the Chicago Outfit, the organisation once run by Al Capone. Another co-owner, also behind a protective wall of fronts, was the former diplomat Joseph Kennedy. The first news of the takeover ran in the newspapers on the day that Kennedy’s son John won the Democratic presidential nomination.

Sinatra once said that he had been attending Democratic Party rallies since before he learned to read the slogans on the banners that his mother made him carry, yet his interest in John F Kennedy seems to have been something closer to a crush. During their brief bromance, the singer campaigned vigorously for JFK, whom he nicknamed “Chickie Baby”, and invited him to pal around with the then nascent Rat Pack – his unofficial club that included Dean Martin, Sammy Davis, Jr and the actor Peter Lawford (who was married to Kennedy’s sister Patricia). When Joseph Kennedy summoned Sinatra to ask for his help in getting John the support of the Mob, the singer flew off to meet Giancana on a golf course. Soon after, the gangster “almost certainly” helped engineer voting irregularities in JFK’s favour in the state of Illinois, Kaplan writes.

If, as Norman Mailer once observed, the dream life of America is made up of a “concentration of ecstasy and violence”, Sinatra is surely that dream life personified. His relationship with killers and extortionists, though unfortunate, has become the stuff of myth and his music is curiously shaded by its seedy implications. Dean Martin’s whiskey-soaked yet tonally perfect delivery evokes an unpolluted sense of warmth and congeniality, even when he purrs sinister lines such as: “Brother, you can’t go to jail for what you’re thinking.” (What could he be thinking?) Yet listening to the Voice, as Sinatra was known, is often a deeper, darker experience, especially on his albums of ballads and what he called “saloon” songs. On Frank Sinatra Sings for Only the Lonely, Sinatra and Strings and No One Cares, the lyrics speak of heartbreak and yearning, but to many 21st-century listeners it is hard to escape the proximity of violence suggested by the singer’s reputation.

It is an undercurrent that, in song, is redirected inwards. We may have heard stories of Sinatra sending an uncomplimentary journalist a tombstone with her name on it, or instructing his driver to go through – not around – the reporters who swarmed him but, in his music, the sense of danger attached to his persona as a star becomes something more abstract. It heightens his performances, making each great song of lost love or longing sound as grand and as important as lost love or longing feels.

There is a desperate seriousness in much of Sinatra’s singing that redeems cliché and shows it to be absolute truth, reminding us that the most profound words we are likely to hear – “I love you” – sound corny and have been uttered billions of times before. “I need your love so badly./I love you, oh, so madly,” he sings in “I Don’t Stand a Ghost of a Chance With You”. Hear a square say this and you may gag. But hear a villain reduced to such depths, a villain who could make anything happen on a whim, and somehow the effect is reversed. There is a strange nobility in the performed debasement of Sinatra, the man who seemed to have it all.

The reality was that he had it all – and nothing at all. Sinatra spent his middle years pining for his errant second wife, Ava Gardner, the screen siren who left him to dally in Spain with one of the toreros who inspired Hemingway’s The Dangerous Summer and whom the obsessed billionaire Howard Hughes jealously had watched by a detective who was later involved in a CIA plot to assassinate Fidel Castro. Success in his various careers placated Sinatra only so long as the sun was up. In the wee small hours, he would stare up at photographs of Gardner, arranged in a shrine in his room, or shoot at them with pellet guns. He couldn’t stand to be alone. “The nights are endless things,” he sings in “When No One Cares”. The lyrics were by Sammy Cahn but in Sinatra’s recording, the singer seems to inhabit every line, every note.

I sometimes wonder what it would be like to listen to Frank Sinatra without any knowledge of his life – would it carry the same weight of lived experience? In the end, any singer’s songs stand or fall on their artistic merits and their emotional resonance with listeners; biography can only have a supplemental relationship with the work. Yet Sinatra was more than a singer: he was a star, and one of the brightest of the 20th century. Who would want to shield himself from that myth and all its violent, ecstatic beauty?

Yo Zushi’s latest album, “It Never Entered My Mind”, is released by Eidola Records. His free Christmas download single “Happy New Year” is available here.