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(Credit: El Daniel Santiago)


Exploring the FBI investigation into Bing Crosby’s ties with the Mafia

Bing Crosby was once America’s archetypal family man. Even today, the singer of ‘White Christmas’ is evocative of a certain cosiness, of hearthside holiday scenes in which rosy-cheeked families in knitted jumpers and sleek dresses decorate their all-American home with festive greenery. However, following his death in 1977, it transpired that Cosby had more than a few skeletons in his closet. Not only was he outed for viciously beating his children, but he was also noted to have had a severe drinking problem – having been arrested for drunk driving as an adolescent. Then, in 1999, a leaked FBI document shed further light on Crosby’s illicit past.

The batch of documents exposed the star as a gambling womaniser who had even stronger ties to the Mafia than his friend and contemporary Frank Sinatra. The similarities of the two singers, it was revealed, went further than their smokey vocals. Sinatra had faced numerous accusations of involvement with the Mafia throughout his career but had always denied them. Unlike Sinatra, however, Crosby’s relationship with New York’s organised crime families was only revealed after his death.

As the documents revealed, Crosby’s links to the Mafia stretch back to his adolescence, a time when he started gambling at illegal dens. As early as 1930, Crosby found himself amid an all-consuming gambling addiction. As one commentator put it, Crosby was “so addicted to gambling and golf that he did not care who he consorted with”. Indeed, he was golf-pals with some of the country’s most legendary killers, including Jack ‘Machine Gun’ McGurn, one of the alleged gunmen in the St Valentine’s Day Massacre, and Bugsy Seigel, the mobster who built Las Vegas and who just so happened to be a friend and henchman of Al Capone.

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But it was his love of gambling, not golf, that landed Crosby in hot water with the mob. His addiction resulted in him owing thousands of dollars to the underworld. Despite being one of the most successful multimedia stars in America, his love of throwing the dice had a huge impact on his income. So, when the American Mafia came calling, Crosby reached into his pockets to find them empty. Not being able to pay, he started receiving death threats in the mail.

As the FBI document reveals, Crosby was so frightened for his own life that he was forced to ask his friends, including Sinatra, to bail him out. When the first letters arrived, they were blunt and simple – as though he was being given a choice: “Bing Crosby, I want you to send me $6,000 right away,” one of them read. But, as Crosby scrambled to get the money together, the reality of his situation was made very clear indeed: “I hate your guts, you bastard. You’re not going to make a fool out of me and if you don’t send it, you’re going to have a rip taken out of you & be put to death by God throu [sic] me and you will have to send all of your money for what you did to me and tried to do.” 

The documents don’t reveal who sent Crosby the death threat, nor do they give any indication of what else – beyond gambling – Crosby did to earn such threats. What is clear, however, is that he was in way over his head. Clyde Tolson, FBI agent friend of the agency’s controversial director J. Edgar Hoover, reported in 1930 that Crosby had been forced to pay off one mobster with $10,000. In addition, the papers suggest that the singer was also responsible for leading his co-star, Bob Hope, astray. One of the agents who contributed to the report observed a police raid on an illegal gambling den in Burbank, California, describing how it contained “approximately 100 patrons, among them Bob Hope and Bing Crosby, [who] were permitted to leave the place”.

Despite being the epitome of middle-class America, Bing Crosby’s past is full of ghosts. Beyond his involvement with the American Mafia, Crosby was also a violent drunkard whose various addictions ruined the lives of those he was closest to. The 1999 FBI file also contains an account from a man who was alleged to have gone on an all-night drinking binge with Crosby and his first wife. According to the report, at one point, Crosby went into a catatonic rage in a nightclub: “Two men held Crosby with guns and four men walked me out and put me in a black Cadillac limousine, hand-cuffed me and took me for a real fast ride and beat me up on route,” the unnamed man recalled. 

We may never know how far Crosby’s connection with the Mafia went. One thing remain’s abundantly clear, however, it’s going to be impossible to listen to ‘White Christmas’ in the same way ever again.

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