Tony Bennett had a life that was as vibrant and nuanced as his soulful tunes. He is known for saying that he left his heart in San Francisco. Bennett’s voice echoed through decades, but his road to fame was strewn with perilous detours, including connections to the Mafia that nearly cost him his life in the vibrant city of Las Vegas.

Bennett passed away on July 21 at the age of 96, but his life stories live on in the annals of show business history. Bennett’s path wasn’t all flawless harmonies and standing ovations behind the scenes. His encounter with the renowned underworld is finally being made public thanks to the revelations of biographer David Evanier.

In his 2011 best-seller “All the Things You Are: The Life of Tony Bennett,” Evanier lifts the lid on Bennett’s early professional problems and the surprising lifeline he received from the Mafia. Bennett’s burgeoning career was financially supported by members of Al Capone’s family, giving him access to coveted nightclub stages all throughout the country. Bennett entered the spotlight thanks to a golden ticket.

But as is sometimes the case with secret agreements, Bennett soon found himself caught in a web of peril and scheming. Evanier claims that Bennett’s encounter with mob hitman Tony Spilotro almost ended in disaster. When Bennett accidentally ran across Spilotro’s girlfriend in 1979, his act at the Sands Hotel & Casino took on a nasty turn.

Bennett was struck by a phone book as Spilotro, whose ruthless reputation served as the inspiration for Joe Pesci’s character in the film “Casino,” released his rage. The singer was discovered lying on the casino floor, an unintended victim of the mob’s complex web of control.

This confrontation turned out to be Bennett’s turning moment. He entered treatment and broke his ties to the Mafia, putting an end to his relationship with the criminal underworld forever. It was a terrible lesson in the dangers of combining organized crime and show business.

But Bennett’s life’s sinister mysteries didn’t stop there. His troubles with drugs and infidelity were discussed by his ex-wife, Sandra Grant Bennett. Sandra alleged that Bennett was a drug-addled “old fool,” stating that the cheery Mr. Nice Guy persona was a mask for a complicated person with problems.

In a last-ditch effort to save Bennett from the grips of addiction, Sandra described how she prevented Bennett from overdosing on drugs. Her open admissions revealed a distinct side of Bennett—one that existed away from the stage’s spotlight and glamor.

Despite the difficulties Bennett encountered personally, his star kept rising. In 2007, the same year he divorced Sandra, he wed Susan Crow. In his final years, he struggled with Alzheimer’s disease, a battle he decided to keep secret from the world until 2021. Bennett’s music and life tales, which highlight the highs and lows of a journey well worth singing about, continue to carry on his legacy. The story of a crooner who danced with the shadows and became a true legend echoes in the hearts of his listeners just as his voice does.