Frank Sinatra remained convinced until the end of his life that Marilyn Monroe had not died by her own hand. He believed she was murdered. That conviction set him apart from the official story, which the Los Angeles Police Department had settled within days of her death. But the people closest to the actress, the details at the scene, and the tangled web of politics, celebrity, and organized crime that surrounded her made the official account difficult for many to accept, then and now.
In the late 1950s and early 1960s, Monroe and Sinatra were two of the most famous people on Earth. Their bond was complicated, and the exact nature of it has never been fully explained. Some who knew them insisted they were simply close friends. Others claimed the relationship ran deeper.
What is certain is that Sinatra felt a powerful need to protect her. According to one account, Sinatra seriously considered marrying Monroe to shield her from the predators and hangers-on who circled her constantly. His lawyer, however, advised against it, arguing that she was too unpredictable and that such a marriage would be a mistake. A friend of Sinatra’s later recalled his reasoning: if she were his wife, no one would dare harm her or take advantage of her.
He thought marriage would give her the space to recover and steady herself. Sinatra’s former road manager told a different story. He said the two were never lovers. But Monroe confided in Sinatra more deeply than she did in almost anyone else.
According to this account, she told him everything about her affairs with President John F. Kennedy and his brother, Robert Kennedy. When those relationships ended abruptly, after she stopped sleeping with them, she was confused and hurt by the sudden silence. She poured out her frustrations to Sinatra, who listened without judgment.
He later explained that despite how attractive he found her, he never pursued her physically. He said he could not bring himself to do it, because he did not want to become just another older man who used her and then discarded her. He cared for her too much for that. A week before her death, Monroe was staying at the Cal-Neva Lodge near Lake Tahoe.
Sinatra owned the resort at the time. What the public did not know was that she was there to spend private time with her ex-husband, baseball legend Joe DiMaggio. She planned to announce their reunion to the press. The media, however, had no idea.
Many assumed she intended to expose her relationships with the Kennedy brothers at a press conference scheduled for the following week. But those who knew her best said she never would have revealed those details, because she still had feelings for John F. Kennedy. Sinatra tried to persuade her to keep living, to give life another chance.
She told him she would not be around much longer. She was right. On August 4, 1962, Monroe was found dead in her Los Angeles home. She was thirty-six years old.
Her housekeeper noticed a light on in her bedroom around three-thirty in the morning and called Monroe’s psychologist and her personal physician. The psychologist arrived first and found her lifeless body. The doctor confirmed her death minutes later. She was lying face down on her bed, naked, clutching a telephone in one hand.
Empty pill bottles were scattered around the room. The coroner ruled that she had died from a self-administered overdose of barbiturates, either accidental or intentional. But the official story never fully satisfied the public, and over the decades, contradictions emerged. Several people connected to the investigation later suggested they had been pressured into supporting a cover-up.
Some hinted that Monroe might have been silenced to protect President Kennedy and his brother Robert. By that point, it was widely known that she had been involved with both men, though the details of those relationships remained murky. Sinatra heard from multiple sources close to Monroe that her death involved more than simple drug use. One account insisted that a suppository had been administered with lethal intent.
Another pointed toward Robert Kennedy or the mafia. Monroe was not just a Hollywood starlet. She had been drawn into the world of organized crime, a world that had taken an interest in her career from the beginning. The mob saw her star power and wanted a piece of it.
Her rise to fame was not entirely her own doing; shadowy figures had helped pull strings behind the scenes. Actor Gianni Russo, who later played a mobster in The Godfather, claimed he had a long and complicated relationship with Monroe that began when he was sixteen and she was twenty-three. He said he was with her at the Cal-Neva Lodge in the days before her death and had a photograph of the two of them taken there. According to Russo, the man behind the camera was Chicago crime boss Sam Giancana.
Russo alleged that Giancana and the mob had targeted Monroe in an attempt to reach the president. The plan, he claimed, was to record Monroe in a compromising situation with John and Robert Kennedy, then use the tape to blackmail the president into invading Cuba and returning casinos to the mob. When the president failed to appear at the resort, the mob had to change its approach. Russo said Monroe learned of the scheme and threatened to expose it to the media.
When Robert Kennedy found out, so the theory went, he plotted to have her silenced to protect the family’s image. Russo was convinced that Kennedy was responsible for Monroe’s death, not the mob. He argued that the mob liked her, knew her reputation for partying, and would have had no reason to kill her. All they would have needed, he said, was a few pills and some strong drinks to get what they wanted.
Russo’s account also included a specific method of murder. He claimed a hitman known as “the Doctor,” a man with a legitimate medical degree who performed hits for the crime syndicate, injected air into a vein near Monroe’s pubic region, causing an embolism that killed her. The coroner, according to this theory, mistook the death for a drug overdose. There were troubling details from that final night that seemed to support the idea that something was wrong.
Monroe made a phone call to Peter Lawford, the British actor married to President Kennedy’s sister Pat. Her voice was slurred and unsteady. She asked Lawford to say goodbye to Pat on her behalf, then to say goodbye to the president, and finally to say goodbye to himself, because he was a nice guy. A few hours later she was dead.
Sinatra, for his part, was not allowed to attend her funeral. DiMaggio, who had never stopped loving Monroe, arranged the funeral himself. He had been devastated to learn of her relationship with Sinatra, since the two men had once been close friends. When Monroe died, DiMaggio made sure Sinatra was not on the guest list, denying him the chance to say goodbye.
DiMaggio also honored a promise he had made to Monroe years earlier. Every week for the rest of his life, he sent roses to her grave. Monroe’s final year was marked by instability. She had struggled for years with depression and substance abuse.
She had not finished a film since The Misfits, and her health had declined steadily. She had been fired from her latest movie at 20th Century Fox for repeatedly showing up late. She relied on a combination of psychiatric drugs to keep herself calm. She once said that the drugs left her feeling somewhat levelheaded and pacified.
None of that meant she was suicidal, but it made the official ruling of self-inflicted overdose at least plausible to some. More than sixty years later, the full truth remains unknown. The official account states that Monroe died of a drug overdose. The theories that she was murdered, either by the mob or by someone protecting the Kennedy family, have never been proven.
What is certain is that Sinatra carried the weight of her death for the rest of his life. Even when his closest friends gathered at his home in Palm Springs, the conversation would eventually turn to Monroe. Sinatra would talk about her late into the night, sharing stories he had never told publicly.
She remained one of the most important people in his life, and her sudden, unexplained death stayed with him always.