Bing Crosby’s Hidden World – FBI Reports Unveil Singer’s Connections to Mafia

There may have been more to the famous friendship between Bing Crosby and Frank Sinatra than what met the eye.

It appears that Crosby, like Sinatra, had ties to mobsters.

Recent FBI findings reveal a troubling side of a man who projected a wholesome image in public but lived a shadowy existence immersed in corruption when off the stage.

The obtained FBI documents indicate that the Hollywood icon engaged in habitual gambling activities and at times had to make payments to underworld associates.

Despite being adored by the American public for his iconic performances in songs like “White Christmas” and roles such as a benevolent priest in “The Bells of St. Mary's,” Crosby was entangled in a world of vice that included illegal payoffs and late-night gambling escapades alongside celebrities like Dorothy Lamour, Bob Hope, and Mel Torme.

His seemingly idyllic facade concealed a darker reality, marked by a history of brushes with the law starting from a young age when he was arrested for drunk driving at 16.

As his fame grew, so did his appetite for women, alcohol, and gambling, leading to the breakdown of two marriages and estrangement from his seven children in pursuit of a high-flying lifestyle and affairs with fellow stars like Grace Kelly and Rhonda Fleming.

The extent of Crosby's questionable associations came to light in the late 1950s when the FBI discovered his social connections with known mob figures, including Moe Dalitz, whom Crosby even invited for deer hunting trips.

Even his love for golf inadvertently led him into the company of dubious individuals, such as Jack “Machine Gun” McGurn, purportedly involved in the infamous St. Valentine's Day Massacre.

Partly a product of the era he lived in, Crosby found himself entangled in a web of racketeers preying on prominent figures in Hollywood, as suggested in a 1930s FBI memo authored by agent Clyde Tolson.

The memo hinted at the pervasive influence of notorious mobsters like Bugsy Siegel and Frank Nitti, with Crosby allegedly paying a hefty sum of $10,000 to ward off a looming threat.

Despite his outwardly charming persona, Crosby's penchant for gambling led him to seek out illicit gaming establishments to squander his vast wealth.

An incident mentioned in a memo described a gambling raid in Burbank in 1947 where Crosby and Bob Hope were among those allowed to leave the premises.

Crosby's volatile temperament also attracted attention, with reports detailing instances of heated disputes during gambling sprees, including one episode in Nevada where an altercation escalated to physical violence.

These confrontations likely contributed to the animosity directed towards Crosby, evident in the menacing death threats he received demanding large sums of money.

The revelations of Crosby's tumultuous personal life, including accounts from his son Gary in the tell-all book “Bing's Boy,” painted a grim picture of a father who inflicted physical and emotional abuse on his family.

Accusations of abandonment, cruelty, and intimidation surfaced, shedding light on the darker aspects of Crosby's character that contrasted sharply with his public image.

Despite his success and wealth, Crosby's legacy is tarnished by the specter of his concealed dealings with criminal elements and the emotional scars left on his family members.

His death in 1977 marked the end of a complex figure whose enigmatic persona continues to intrigue, shrouded in mystery from his birth without official documentation to his ambiguous birthday that remains a well-guarded secret.