Bing Crosby, The All-American Hero With Dark Ties To The Mob

He was one of America’s most beloved entertainers. As a star of radio, TV and film, his legacy has endured for the best part of a century. The holiday period just wouldn’t feel complete without hearing his perennial classic “White Christmas.” But entertainer Bing Crosby apparently harbored some pretty dark secrets. FBI reports, in fact, reveal some shady links to the Mafia.

A picture-perfect veneer

Bing Crosby’s illustrious career was rooted in wholesome family entertainment. The hefty PR machine surrounding him did a great job of painting the singer and actor’s life as that of a loving husband and doting father.

But the reality playing out behind the scenes wasn't all as it was being engineered to look to Crosby’s legions of fans. Behind the glossy veneer, something more human was at play. 

Nefarious past

Anyone with an in depth knowledge of Crosby will be aware of his nefarious past. Like the time he was arrested for drunk-driving when he was just 16 years old.

But many believed that the crooner had left his wild ways in the past, particularly after his first marriage to Wilma Wyatt, better known by her stage name, Dixie Lee.

Dixie and Bill

The budding young couple met when they were just 20 years old. In a whirlwind romance, Lee and Crosby married just as the latter’s career was starting to take off.

And since his new wife’s own career was already well established, the pair soon became darlings of the media across the United States. But scratch the surface, and not everything was picture perfect.

Painted as a villain

Just six months after their wedding, Lee requested a divorce on the grounds of “mental cruelty.” The story rocked Hollywood, not least because the details painted Crosby as the villain.

But the conflict was short lived, and the newlyweds reconciled just one week later. Any hopes for a wholesome, all-American family image, however, appeared to be damaged beyond the point of repair.

Divorce number two

As Crosby’s popularity increased, so did the number of invitations he received to lavish parties. Lee often accompanied her husband on these social occasions, despite being somewhat of a wallflower.

She would drink in an effort to be sociable, but when she tried to match Crosby’s pace, things would apparently get out of hand. This time it would be the crooner who contemplated divorce.

Plagued by rumors

And yet the couple stayed together. What's more, they were making every effort to put on a united front. Crosby even held an overnight vigil by Lee’s hospital bedside when she was struck down with a respiratory infection.

Over the years, Lee and Crosby had four sons: eldest Gary, twins Phillip and Dennis, and lastly Lindsay. But rumors about the couple’s private life continued to plague their relationship.

A family sawn in half

Along with the deluge of rumors that followed the course of their marriage, so came the constant murmurings of divorce. Speculation was perhaps fueled when the couple reportedly spent time living apart.

Whatever the truth, Crosby was understandably devastated when Lee passed away from ovarian cancer just three days shy of her 43rd birthday. It was 1952, and the loss left the famed entertainer in tatters.

“I will never talk about my grief at losing her”

Crosby paid tribute to his first wife in the wake of her passing. He said, “I will never talk about my grief at losing her. But in the years ahead I’m going to sorely miss her love, steadfast and constructive support.”

Lee was was buried in the Crosby family plot on November 3, 1952, and once the dust had settled following her funeral procession in Beverly Hills, the reality now doubt dawned on the now widowed father of four boys, whom by that time were in their teens.

Moving on

After grieving, the actor later engaged in relationships and affairs with high-profile partners. Among them were the likes of model and actress Pat Sheehan, screen icon Grace Kelly, and prolific actress Inger Stevens.

It was five years after his first wife’s passing that Crosby married again, this time to actress Kathryn Grant. Although their union lasted 20 years until his death, it wasn’t without its difficulties.

Crosby's son speaks out

The couple eventually had three children of their own, Harry Lillis III, Mary, and Nathaniel. And though there were persistent rumours of Crosby’s infidelity, worse allegations were made about the singer after his passing.

They surrounded the entertainment star’s alleged ill temper and were made by his very own son: his eldest, Gary. Six years after his father’s passing, the younger Crosby released what was apparently a tell-all book that would damage his dad’s wholesome reputation.

A cruel man?

Gary described a man who lacked emotion and was distant from his son. The crooner was a cruel man, according to his eldest son, and would often mock him about his supposed excess weight. And there was more.

In the tell-all book, Going My Own Way, Crosby’s son recalled his father taunting him with names like “Bucket Butt” and “My Fat Kid.” He described his father beating him if he missed his target weight.

Or just a publicity stunt?

And he told stories of he and his siblings being ridiculed if they didn’t clean up after themselves. Yet Gary’s siblings dismissed the book as pure fantasy, saying their brother was merely publicity seeking.

According to the Newsner website, Phillip Crosby said in an interview with People magazine, “My dad was not the monster my lying brother said he was; he was strict, but my father never beat us black and blue, and my brother Gary was a vicious, no-good liar for saying so.”

The damage was done

Mary Crosby, too, supported Phillip’s assessment, saying Gary regretted speaking out. She claimed in the Daily Express newspaper, “Gary said to me that the publishers had told him, ‘The worse it was, the more books would sell.’ And he was very clear about why he did it... Years later he apologised profusely to us but by then the damage was done.”

So what of the life Crosby was really living? With his high profile, it’s possible that much of the speculation about his private life was pure tabloid fodder. But was any of it founded on truth?

Guilty by association

When your friends and colleagues include notorious Mafia ally Frank Sinatra, tongues have no choice but to begin wagging. That doesn’t mean he’s guilty by association, though. Or does it?

Crosby was a longtime associate of Ol’ Blue Eyes. But whereas the “New York, New York” singer did little to hide his Mob connections, it wasn’t a world his contemporary was necessarily implicated in.

The JFK connection

And Crosby’s image was far more wholesome than Sinatra’s, to the point the White House turned to the “White Christmas” crooner to indulge their own. Sinatra had, of course, hosted then-President John F. Kennedy’s inauguration party in 1961.

But due to the singer’s association with Mob boss Sam Giancana, the White House took a different tack when he was due to host a different party for JFK.

A snub with consequences

Instead, the President’s cabal were encouraged to stay at Crosby’s own home in Coachella Valley, with the hopes of avoiding any shady connections causing problems. But Kennedy’s snub of Sinatra had consequences.

The “My Way” singer dismissed the President’s brother-in-law Peter Lawford from the cast of the musical comedy Robin and the Seven Hoods. And, you guessed it, enlisting Crosby as his replacement.

More than just affairs

The movie is set around the Chicago Mob, and it was the closest association the “White Christmas” singer had with the Mafia. Or so people believed. Because since Crosby’s passing in 1977, stories about the cardigan-wearing, golf-playing entertainment legend came bubbling to the surface.

And they were tales that weren’t entirely in keeping with his wholesome image. While some were confirmation of long-standing rumored affairs, others might ruin the holidays any time you hear “White Christmas.”

Dangerous liaisons

In 1999 FBI documents were released that exposed the type of company the singer kept on the golf course. They suggested that Crosby’s drinking habits were not as far in the past as presumed and that rumors of infidelity were perhaps more tame than suggested.

Plus, the crooner’s associates may have been far more questionable than those of Frank Sinatra. Really? Well, Crosby had already recalled one incident in his Call Me Lucky autobiography.

One night in 1929

In the book, the singer described a booze-fueled night in 1929 where he'd found himself in the company of a known gangster and participant of Chicago’s St. Valentine’s Day Massacre.

According to accounts, Crosby passed out. But when he came to, his new friend suggested sticking with them for a while since a shooting had occurred earlier in the night.

Not a one off

In an attempt to pull himself together, Crosby stumbled to the bathroom. But as he freshened up there was noise that he presumed to be six misfiring cars. People started screaming.

In the short time the singer was in the bathroom, his new friends’ rivals had showed up and sprayed the group with bullets. Yet the FBI papers suggest this was not an isolated Mob connection.

Illicit dealings

Because, as the reports suggested, the glitzy nights out with fellow celebrities like Bob Hope, Mel Torme and Dorothy Lamour were reportedly taking place to mask something far more sinister.

According to the documents unearthed by the website APB News, not everything with Crosby was as it seemed. The papers paint a picture of a womanizer, in fact, with a raging temper who frequented illegal gambling dens. 

Busted with Bob Hope

One document described an incident in Burbank, California where Crosby was hanging out at a gambling den when it was raided. The paper said, “Approximately 100 patrons, among them being Bob Hope and Bing Crosby, were permitted to leave the place.”

So not only was Crosby on the wrong side of the law, but the documents suggest he was dragging his friend Bob Hope there, too. APB News also published correspondence from someone who knew Crosby in his early career.

Violence and excess

According to the website, this gentleman wound up on an all-night drinking session with the singer and his first wife in Nevada. And although it wasn’t specified what provoked it, the man witnessed the entertainer fly into an apoplectic rage in an illegal club.

But that wasn’t all there was to the story. According to the letter’s author, “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 [en] route.”

“Machine Gun” McGurn

So what about Crosby’s Mob connections? Well, that’s something the singer’s own biographer, J. Roger Osterholm, was keen to play down. Because one of Crosby’s golf buddies was Jack “Machine Gun” McGurn, the St. Valentine’s Day Massacre mobster we met earlier.

But, according to Osterholm, their association didn’t stretch much further than the golf course. Yet it’s been suggested that figures from such opposing worlds would struggle to fraternize in the same establishments by accident.

Friends in dangerous places

Plus Sinatra’s connections to such nefarious characters was so well documented that they were investigated by authorities at one point. Is it too much of a stretch to think Crosby kept similar company for more than the odd round of golf?

Well, Crosby’s friendships within Mafia circles certainly did run deeper than “Machine Gun” McGurn, according to the FBI. The entertainer maintained a relationship with gangster Bugsy Seigel, a driving force behind the construction of the original Las Vegas Strip.

A compulsive gambler

And Crosby counted one of Al Capone’s henchmen, Frank Nitti among his friends. Perhaps the word “friend” is putting the relationships too lightly. Because Crosby, allegedly a compulsive gambler, once made a payment to a gangster to the tune of $10,000, back in 1930.

Today that would be a bill of more than $160,000. Ouch. This testament came from former FBI agent, Clyde Tolson. And Crosby often received death threats in relation to the debts that he accrued, according to the website Independent.ie.

“I hate your guts”

The site alleged that the singer even stumped up for one price tag in order to get a hitman off his back. According to the FBI’s files there could be more than a little weight to this theory.

An unsigned letter contained in the FBI files read, “Crosby, I want you to send me $6,000 right away. I hate your guts... You’re not going to make a fool out of me. You will send me all of your money for what you did to me and what you tried to do.”

Squandered his millions

It is claimed that Crosby is one of the wealthiest entertainers of all time. Not only was he a hugely prolific actor, recording artist and radio broadcaster, but he had other interests, as well.

He was a savvy investor in baseball teams, race horses, cattle ranches, oil wells, mining, real estate, music publishing and TV. So Crosby accrued wealth in the multi-millions by his early 30s. Much of it he is said to have squandered on his passion for golf and addiction to gambling.

Paying off the mob?

Perhaps he felt he could buy his way out of trouble, as it’s alleged he did by paying off a mobster. As for his wild personal life? Well, it was easy for him to hire the best Hollywood PR firms to play that down.

Yet the FBI reports that emerged in 1999 were not the result of a direct investigation into Crosby’s himself. Rather they were the surveillance notes tracking the gangsters the singer often associated with.

An alternate theory

It’s entirely possible, then, that Crosby’s connections to the Mob were entirely innocent. That’s certainly the belief of one ardent fan. Malcolm MacFarlane, who edits the Crosby-dedicated fan magazine Bing, dismissed APB News’ report as sensationalist.

After reading through all the files on Crosby released by the FBI, MacFarlane concluded that the only mention of Siegel and Nitti came in APB News’ article. Plus the fan had a different take on his idol’s $10,000 payoff.

A bribe, a scam, or an act of kindness?

MacFarlane slated the editors of the New York Post, calling out a similar article as bogus. He wrote in reference to one of the files released, “The memorandum from Tolson to Hoover starts out mentioning that Hollywood is ‘overrun at the present time with all types and kinds of racketeers, who are preying upon prominent persons in the motion picture industry.’”

It wasn’t, however, a bribe. The conclusion that MacFarlane drew was that Crosby sent $10,000 as financial assistance to someone he understood to be in need. MacFarlane believes it was a scam, and that his idol acted with the best of intentions.

The mystery remains

That would certainly be more in keeping with the wholesome all-American hero whose work is still cherished today. The truth may be something Crosby took to his grave after the heart attack he suffered on October 14, 1977.

Either way, his life was one lived with the same veil of mystery as the day he was born: without a birth certificate, no one could say for sure when that was. That the crooning legend never clarified the exact date in May 1903 suggests that’s the way he would have liked it.