Sinatra, Marilyn and the Kennedy Rumour Mill

Tony Oppedisano, once a road manager to Frank Sinatra, has written a memoir, Sinatra and Me: In the Wee Small Hours. As Newsweek reports, the book has raised eyebrows within the Sinatra family circle, with Eliot Weisman – the singer’s stage manager for the last two decades of his life, and co-executor of his will – suggesting that some of Oppedisano’s claims may be exaggerated.

“Sinatra and Oppedisano were more than three decades apart in age, but Oppedisano explains in his book that Sinatra came to trust him through his association with their mutual friend Jilly Rizzo, who was a close Sinatra confidante before he died in 1992. [Ermenigildo ‘Jilly’ Rizzo was a New York restaurateur. Sinatra died in 1998, six years after Rizzo.]

The book’s 320 pages wade through Oppedisano’s memories of his first Sinatra album purchase at age 13, his introduction to the legendary crooner at a Manhattan bar in 1974, and his eventual role as Sinatra’s road manager during the final few years of the late crooner’s touring career.

Weisman said he was given an advance copy of Oppedisano’s book, most of which he said he believes is ‘exaggerated.’ In the chapter that deals with the events surrounding the recording of Duets, Weisman said the writing paints Oppedisano as an ‘integral’ part of the recording process. [Duets, Sinatra’s final studio album was released in 1993.]

Oppedisano and Weisman both say that Rizzo played an early part in igniting the idea behind Duets, but their retellings of how the album came to be differ from there … ‘Tony Oppedisano had nothing to do with Duets,’ Weisman told Newsweek.

‘As long as I’m alive, I will protect him,’ Weisman said of Sinatra. ‘If you had Sinatra as a friend, you didn’t need any more friends. He was a one-and-only, a champion of the underdog. And anything I can do to help protect him, his name and likeness, I will do.'”

Ahead of its release, an excerpt has been published in People magazine, in which Oppedisano claims his former boss believed Marilyn was murdered. But as Oppedisano only met Sinatra twelve years after Marilyn’s death, he was not a witness to the events he describes – whatever his boss may, or may not have told him many years later, ‘in the wee small hours of the morning.’ It is rather distasteful that People magazine chose this excerpt from Sinatra’s book, when his relationship with Marilyn was only a small part of his extraordinary life.

“‘Frank believed she was murdered,’ he writes, ‘and he never got over it.’ According to Oppedisano, Sinatra and Monroe were close friends but not lovers. While Sinatra thought she was beautiful and funny, he writes, ‘Frank felt she was too troubled, too fragile, for him to sleep with and then walk away.’

She did however confide her most intimate secrets including her affairs with John F. Kennedy and Robert F. Kennedy. When the affairs ended abruptly, he continues, ‘Marilyn told Frank she didn’t understand why they’d shut her out completely once she stopped having sex with them.’

The weekend before her death, the actress spent time at the famous Cal Neva Lodge, outside of Lake Tahoe, partially owned by Sinatra. What the world didn’t know, the author reveals, was that she was there to spend time with her ex-husband Joe DiMaggio who was staying nearby and that she had decided to make a press announcement the following week that they were getting back together.

The news of a press conference sparked a rumor that Monroe was going to share details of her relationships with JFK and RFK. But, Oppedisano writes, ‘Frank said she’d never have spilled about the Kennedys because she still had feelings for [Jack.]’

And he says, ‘Frank believed if the press conference hadn’t been announced, she would have lived a lot longer.’

Within days of Monroe’s death, he writes, Sinatra’s attorney Mickey Rudin, who also worked with Monroe, told him that the actress had been killed. It was a rumor also circulating among Mob Boss Sam Giancana’s men, some of whom claimed involvement. According to the book, Sinatra had several sources who told him the same story: ‘She’d been murdered with a Nembutal suppository and Robert Kennedy or the Mob was involved.’

Over five decades later, the truth remains a mystery. ‘Conspiracy theories abound and I can’t lay them to rest,’ writes Oppedisano. What he does know, is that Sinatra remained haunted by her death.”

Actually, Frank and Marilyn had been lovers, on and off, throughout 1961. This was commonly known within her circle of friends, and Marilyn herself mentioned it in a letter to her psychiatrist, Dr. Ralph Greenson. The relationship ended when Frank became engaged to Juliet Prowse, but they remained on good terms until Marilyn’s death. Other sources – including Jilly Rizzo (see here) – have suggested that Frank wanted to marry Marilyn, but after three divorces, she wasn’t ready for another commitment.

While she remained close to Joe DiMaggio, Marilyn said publicly that they were not a couple (“there is nothing to reconcile.”) Some friends of DiMaggio hoped they would remarry, but none among Marilyn’s circle believed she would. There is no concrete evidence of any wedding plans.

Furthermore, the ever-possessive Joe had abruptly ended his long friendship with Frank when he began dating Marilyn, and there is no evidence to support the rumour that Joe joined Marilyn at Cal-Neva on the weekend before she died. Therefore, Frank would have had no part in Marilyn’s ongoing relationship with Joe.

Frank was a vocal supporter of John F. Kennedy’s presidential campaign, but their friendship cooled after Kennedy took office. Whatever encounters Marilyn may have had with the Kennedy brothers, it’s highly unlikely that she would have confided in Sinatra, a former lover with a jealous nature and explosive temper!

As for the theory of a Nembutal suppository, it seems implausible that Marilyn could have ingested such a high dosage in that way. It is far more likely that she took the overdose orally, whether by accident or intent. Milton Rudin, who was Marilyn’s lawyer as well as Frank’s, never claimed that Marilyn was murdered in his interviews on the subject, but he was well aware of her emotional problems and addiction to sleeping pills.

It’s possible that Sinatra, like many others, was swayed by the conspiracy theories about Marilyn’s death and the Kennedys that appeared in the 1970s. But at the time of her death, this was not a widely-held view, except by a small handful of far-right cranks with a rabidly anti-Kennedy agenda. Unfortunately, lurid gossip about Marilyn’s demise has become something of a cottage industry in this era of ‘fake news’, and a very profitable one for those who propagate it.

Whether Sinatra really told Tony Oppedisano that Marilyn was murdered is impossible to say, but even if Frank did come to believe this, it does not mean that his opinion should override the conclusions behind the original inquest (that her death was a probable suicide), or the 1982 LAPD review (that there was no credible evidence of murder.)