"Sinatra and Me: In the Wee Small Hours"

“Everybody wanted to know Frank Sinatra; almost nobody really did. Tony Oppedisano really did…. Utterly clear-eyed yet truly loving, Sinatra and Me is a matchless portrait of a flawed, brilliant man―and of a great friendship. A gem of a book.” ―James Kaplan, bestselling author of Frank: The Voice and Sinatra: The Chairman

“What a great book!  Tony O. does here what many have tried to do without quite succeeding: he’s made Frank Sinatra accessible… Certainly, this is one of the very best of the Sinatra books and, I daresay, maybe the only one the man himself would actually read!” ―J. Randy Taraborrelli, New York Times bestselling author of Sinatra: Behind the Legend

For months in 1947, Lee Mortimer had been circulating rumors that Frank had ties to the Mob. When the two men accidentally encountered each other in the entrance of Ciro’s restaurant a month before Mortimer visited the FBI, Mortimer murmured “Dago” as he passed Frank. For Italians in the forties, dago was the equivalent of the “n-word” for African-Americans. Italians might call one another “dago” affectionately, as Frank and Dean Martin did. But coming from a non-Italian, the word was a reason for fisticuffs. Frank decked Mortimer with a left hook and paid the resulting fine with no regrets. In May 1947, New York Daily Mirror reporter Lee Mortimer sat down for a chat with FBI agent Clyde Tolson, J. Edgar Hoover’s right-hand man and reported life partner. Mortimer was about to publish another piece on Sinatra and wanted help from the FBI in collecting dirt on Frank. The newsman handed Tolson a picture of Frank with a man whom Mortimer thought looked like a gangster and said he’d also heard a rumor that Frank’s godfather, underboss Willie Moretti, had originally backed Sinatra’s career. Mortimer then mentioned hearing allegations of a “sex arrest” of Sinatra in 1938. This was just the kind of stuff Hoover was looking for. The FBI was only too happy to give Mortimer what he wanted. The deal was done to the satisfaction of all parties, and Mr. Hoover could be assured of Mr. Mortimer’s understanding the terms. So continued the long, sordid history of the cooperation between our federal government and muckraking journalism, carefully recorded in an FBI file titled “Francis Albert Sinatra.” 

The allegations made the careers of dozens of journalists and, in their endless spin-offs, created a legend that destroyed the reputation of an American citizen. From the day Lee Mortimer published his first article on Sinatra and the Mafia, until Frank died fifty years later, the top secret FBI file was supposed to be the smoking gun proving Frank’s role in the Mob. Lurid biographies made vague references to it whenever they wanted to smear Frank. When the file was finally released a few months after Frank’s death, showing no evidence of Mob ties had ever been found, it made no difference. Nobody wanted to read a dull thirteen-hundred-page file debunking stories the public was already in love with. The FBI “sources” often turned out to be the gossip columnists themselves, but the press didn’t exactly rush forward to clear Frank’s name when the file was published. Frank loved to joke that the initials FBI stood for “Forever Bothering Italians.” No kidding. Nancy Sr. had a cousin who became a soldier for a Mob guy named Willie Moretti, who was chosen by Marty Sinatra as Frank’s godfather at his baptism. Neither Nancy nor Frank got involved in Willie’s “business.” Years later, though, when the press found out that Frank was Willie’s godson, they pounced on it. 

“Young Sinatra’s Career Financed by Mobster.” Tipped off by the press, the FBI later added a note in Frank’s surveillance file that the Mob (again in the person of Willie Moretti) was “forcing” Frank to leave Ava Gardner and go back to Nancy. Sam Giancana, who took over as the boss of Chicago in the years after Capone, was one of the owners of a club called the Black Orchid. Frank played there. All the big guys played there, including Don Rickles, Danny Thomas, and Bing Crosby. Since their last names didn’t end with a vowel, however, no one cared. Frank used to get frustrated and say to me, “The joints weren’t exactly owned by Cardinal Spellman! I didn’t know any bishops, cardinals, or monsignors who owned nightclubs. Otherwise, I would have ended up rubbing elbows with them!” Clubs were highly attractive to Mob guys. They provided an environment that fit the mobster’s day-to-day lifestyle, where they never knew if there was going to be a tomorrow. Frank made a parody out of it and used to say to me, “Live each day as though it’s your last, and one day you’ll be right.” He also used to joke, “Anyone who’s dumb enough to take a nap in the trunk of a Cadillac deserves to be shot in the head”!

Everything changed when Lee Mortimer wrote an article about Frank’s trip to Havana in 1946. Frank had been performing at the Fontainebleau nightclub in Miami, the premier place to work at the time, owned by the usual Mob connections. Wiseguy Joe Fischetti came down from Chicago regularly to check on the business. Joe was an easygoing guy, and he and Frank would hang out and share a drink after the show when Frank was performing there. One night, Frank was complaining to Joe that he needed a vacation, and he was thinking about going to Cuba for a break. He’d heard that the Havana nightlife was hot, and so were the women. Mortimer and another Hearst writer, Westbrook Pegler, wrote a whole series of articles about Frank’s activities as a so-called Mob courier. Because journalists copy from each other, the stories spread like wildfire. No protests or threats of legal action on Frank’s part fazed the press. Frank was angry and increasingly desperate to stop the stories from spreading further. What happened next is something only I know. I’d never heard the tale until Frank told it to me in vivid detail. It’s the story of the day Frank Sinatra met newspaper tycoon William Randolph Hearst, the inspiration for the iconic film Citizen Kane (1941). 

The whole experience was like something out of a movie. The meeting with Hearst came about because of Nancy Sr. Nancy was good friends with gossip columnist Louella Parsons. Parsons, in turn, was old friends with silent-film star Marion Davies. Marion Davies was the live-in mistress of William Randolph Hearst, whose newspaper empire was the biggest in the world. Mortimer and Pegler were both Hearst writers. Louella contacted Marion Davies for Nancy Sr., and a one-on-one private sit-down between Frank and Hearst was arranged. The face-to-face was to take place at Hearst Castle in San Simeon, California, under the strictest secrecy. Frank, Nancy Sr., and Louella Parsons drove north to San Simeon together for the meeting. For anyone who has ever seen it, the first sight of Hearst Castle, an art deco masterpiece, is spectacular. This was Frank’s first sighting. He told me he was awestruck by the sheer beauty of the place, astonished by its size. When he, Nancy, and Louella parked and got out of the car, the front door they approached looked like the entrance to a fortress. They rang the bell and they were very surprised when Marion Davies herself opened the front door to welcome them. In the towering entrance hall, Miss Davies spoke briefly with Nancy Sr. and Louella, then guided Frank down the hall to the library. Frank was very nervous as he waited for Hearst that afternoon, mentally rehearsing what he was going to say. After a few minutes, the big door to the library opened, and Hearst was pushed into the room in a wheelchair. 

Physically, he looked frail, but his face revealed a mind and will that were still strong. His attendant parked him across the table from Frank and then left the room. Without preliminaries, Hearst said to Frank, “What do you have to say to me?” Frank pleaded his case with all the passion he possessed. He told Hearst that Mortimer and other Hearst journalists were creating an elaborate lie about him. He said that he wasn’t a Communist or anti-American or affiliated with the Mob. Hearst promised to help Frank. Frank sat there for a while pondering what had just happened, until Marion Davies came in to guide him back to Nancy. For a few months, Hearst’s ultimatum was respected. The result was a brief moratorium on Frank in the Hearst press. But not long afterward, Hearst left San Simeon to seek medical care for what would be his final illness. His sons took over the running of the papers, and editorial policies shifted. Frank’s reprieve was a short one. Frank used to say about the press, “All day long, they lie in the sun. And after the sun goes down, they lie some more.” Even if William R. Hearst had lived longer, you can’t unring a bell. The damage to Frank’s reputation was done. Once Mortimer opened that door, the word was out that the feds wanted dirt on Sinatra. Unnamed informants flocked to the FBI. Informants volunteered information on Frank in hopes of avoiding prosecution themselves. J. Edgar Hoover lapped it up. Journalists continued to meet with FBI agents. In 1957, journalist Bill Davidson asked the FBI for derogatory information on Frank that he could use in what became a three-part series he was writing for Look magazine. IRS asked Frank Sinatra: Have you ever had any business dealings with Mr. Giancana? Frank's reply: None. 

Neither the IRS nor the FBI believed him. The government’s suspicions became a problem whenever Frank wanted to invest in something. Being business savvy, Frank had always dreamed of owning his own club. Las Vegas, where he headlined starting in the fifties, seemed the obvious place. The Flamingo was a lucrative possibility, but Frank told me he didn’t want to be at the Flamingo because that had been out-and-out owned by mobster Benjamin “Bugsy” Siegel. When Frank started appearing at the Sands, that seemed more like the kind of place he’d like to be involved with. So many writers talk about Frank’s fascination with the Mob, but in reality, it was the other way around. The Mob, like the rest of the world, was fascinated by Frank. He possessed incredible charisma. Everyone wanted to bask in it, including mobsters. The Mob guys especially admired Frank because they recognized that he’d pulled himself up by his bootstraps—with his charm, sometimes with his fists, but most of the time with his voice and innate talent. He did it on his own—his way—not with Mafia money.

Frank and Marilyn were close, and he idolized her. She was beautiful and funny and charismatic and radiated sexuality. She was also as fragile as a troubled child, always looking for a man to take care of her and make her feel safe. Frank knew her for years, and they’d had a romance of sorts. Contrary to widespread belief, however, Frank never slept with her. He told me he badly wanted to, that he was terribly attracted to her, but he always stopped short. Marilyn was more than willing, but Frank felt she was too troubled, too fragile, for him to sleep with. He just couldn’t get rid of the feeling that sex with her would be taking advantage of her. They were close, though, and Frank was her confidante right up to the end of her life. The weekend before her death, Marilyn came up to Cal-Neva Lodge to stay in one of the bungalows and figure out the next step in her life. Privately, she was there to spend time with Joe DiMaggio. Joe had never gotten over Marilyn, and in her usual fashion, she looked to a man, a father figure, to fix her life for her. She decided Joe was the refuge she needed. Marilyn spent most of the weekend holed up in private with Joe.

She decided to make a press announcement the following week, saying they were officially back together. Once the press conference was announced, however, the rumor started that she was going to publicly rat out the Kennedys and Sam Giancana. In reality, Marilyn had no intention of going public with what she knew. Frank said she’d never have spilled her guts to the press about the Kennedys. Frank told me it was Marilyn’s death that was the final nail in the coffin between him and Peter Lawford. When everything spiraled down with Marilyn, Lawford did nothing to help her. As Frank saw it, Peter could take care of himself, but Marilyn couldn’t. Frank thought Lawford should have protected her. Within days of her death, Frank’s friend and attorney Mickey Rudin, who was told of Marilyn’s death six hours before the police were, told Frank that Marilyn had been murdered. The same rumor was circulating among Sam Giancana’s men, some of whom claimed involvement. Frank found it unbearable that such a damaged, vulnerable, helpless human being had lost her life because some powerful men feared what she might say. The assassination of Jack Kennedy a year later compounded Frank’s sense of grief and loss. He never got over losing either to premature and unnatural deaths.

Thirty years after JFK’s death, on November 22, 1993, Frank and I stopped over in Palm Springs for a brief hiatus in a heavily booked two-month tour. We got in at one a.m., drove to the compound, and slept for a few hours. That night, as usual, Frank and I watched the eleven o’clock news on the Palm Springs CBS affiliate. The reporter was doing a piece on the 30th anniversary of John Kennedy’s assassination. Frank started talking to me, reminiscing about Jack Kennedy. Gradually, the conversation drifted to Marilyn Monroe. In the hours before dawn, in the vast silence of the desert, Frank talked to me about his friends Marilyn Monroe and John Kennedy. His words rose and fell in a soft rhythm I can only describe as a lament. Three decades later, his pain and anger at their passing still haunted him. 

Frank once told me he’d never met a man who could give another man advice about women. “I’m supposed to have a PhD on the subject, but I’ve flunked out more often than not. I’m very fond of women; I admire them. But, like all men, I don’t understand them.” He enjoyed women, but he also had a lot of respect for the fairer sex, something he learned from his mother. Frank loved the ritual of courtship and seduction. He liked to pamper a woman, buy her gifts, make her feel like a queen. Frank knew what he wanted sexually, and he seemed to know what they wanted, too. But he’d rarely jump into bed upon first meeting someone. He was never a Wham, bam, thank you, ma’am kind of guy. He was surprisingly protective of a woman’s reputation. He’d drive a woman home after a date and see her to the door. Women never had to do the walk of shame with Frank. Some of Frank’s love affairs started as friendships and went from there. Many of his romances ended as lifetime friendships, including with the women he married and eventually divorced. As I’ve said, Marilyn Monroe was a woman Frank considered off-limits for ethical reasons. 

Another widely publicized example is Natalie Wood. Books about Frank nearly always state that Frank had an affair with Natalie Wood when she was a fifteen-year-old starlet, and he was nearly forty. It sounds sleazy, and it would be if it were true, but it isn’t. Frank was involved with Natalie when she was older, in between her two marriages to Robert Wagner, but never when she was a young teen. I talked about the allegation recently with my friend Robert Wagner, who was appalled by the story. He told me in pretty colorful language that it was absolutely untrue. He and Natalie had been close friends with Frank and discussed him many times. R. J. felt certain that she’d had a romantic relationship with Frank later in her life, but never as a teen. Frank told me once, “When Ava was relaxed, she could have a mouth like a truck driver. She drank as well as I did or better.”

Frank and Ava’s relationship was like fire and ice, either burning hot or ice cold. When their relationship was hot, it worked for a while, but when it cooled off, it was freezing, and Frank would be miserable. Their arguments were legendary. Frank said they were too much alike in all the wrong ways. She was a ball of fire with a red-hot temper like his. At the end of the day, Frank was afraid of what might happen if he said no to his fourth wife Barbara Marx. When he did say no to something she desperately wanted, she’d pull out the most effective tool in her arsenal, withdrawing her company. She wouldn’t talk to him or even see him for days at a time. It was Frank’s worst nightmare. When he was a kid, he was terrified every time his parents left him alone all night, frightened they’d never come back. He’d grown up fearing Dolly’s disapproval. As an adult, he had trouble coping with any strong-willed woman he loved. The thought that Barbara might leave him was more than he could face. My own relationship with Barbara Sinatra was complex. It wasn’t always an easy one, but I had real affection for her. I used to call her every year to wish her a happy birthday. When she’d pick up the phone in Palm Springs, I wouldn’t even say hello. I’d just start to sing “Happy Birthday.” Twice she thought it was Steve Lawrence singing, and I was very flattered. Even after Frank was gone, Barbara and I remained friends. —"Sinatra and Me: In the Wee Small Hours" (2021) by Tony Oppedisano

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 – 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. Furthermore, the ever-possessive Joe had abruptly ended his long friendship with Frank when he began dating Marilyn. 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. 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 Monroe’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. Source: https://themarilynreport.com