Nancy was speechless. Frank was not. “What is it?” he continued to challenge her, his face inches from her own. “You don’t have enough money? We don’t live a good life? I’m not a big enough success? What is it? You tell me.” It was as if he just couldn’t stop himself; he was out of control.
Nancy burst into tears and left the room.
“All right,” Frank announced to the stunned remaining guests. “Everybody out. Out. Out. Out! Happy fucking New Year’s. Now get the hell out. Show’s over.”
Frank and the Mob
One of the most enduring rumors about Frank Sinatra is that he was deeply involved with the Mafia. The first stories of this nature began to circulate after his attorneys and agents extricated him from the Tommy Dorsey contract. Because it was so well known that Dorsey had been adamant about holding Sinatra to his deal, when he was free of it so suddenly, rumors had it that the singer’s underworld friends had intervened on his behalf. Of course, the motley crew from Hoboken who, at Hank Sanicola’s direction, actually did intervene could hardly be considered dangerous gangsters. The Dorsey business aside, the most lurid and persistent stories connecting Sinatra to the mob actually started in 1947, a few years after the contract was settled.
Frank Sinatra would always claim that the reason he was picked on by certain members of the press and accused of being a friend of the Mafia was his Italian-American heritage, because his name ended in a vowel. He and his family labeled the charges “discrimination.” Their position was understandable, but why was it that other Italian Americans, such as Vic Damone, Perry Como, even Al Pacino (who actually went on to play a godfather in the series of films by that name), were not similarly persecuted because of their vowel-ending last names?
Frank and his family also suggested that many nightclubs in the 1940s and ’50s were run by gangsters, and that if a person wanted to work in show business, he or she had to some extent to do business with the underworld. This appears to be true.
However, Frank was also guilty of poor judgment when it came to the people he socialized with when he wasn’t working. When it came to the underworld, he couldn’t seem to help himself. Going all the way back to his first exposure to uomini rispettati during his early days in Hoboken, he was always fascinated by colorful mobster types. These were men who, in his view anyway, were powerful enough to get away with pretty much anything. He found it an admirable way to live, and he sought to comport himself the same way—not to be bound by what might be considered normal behavior when it came to his marriage or even in how he dealt with those in his social circle. He did things his way, no matter what anyone thought of him. He expected complete loyalty, even though he often didn’t demonstrate it himself. If someone crossed him, that person was banished from his life forever. “It was as if he was a mobster in his own world,” is how Peter Lawford once so aptly put it. “He hero-worshipped those underworld guys, and then he treated people in his own life like he was a mob boss, like he was a don.”
In January 1947, thirty-one-year-old Frank was asked by Joe Fischetti, a buddy he had known from Hoboken since 1938 (and cousin and heir of Al Capone), if he would like to meet the boss of the Cosa Nostra crime syndicate, Lucky Luciano. Thirty-nine-year-old Luciano, who had been in exile in Havana since late October 1946, was living the good life in a spacious estate in the exclusive Miramar suburb among the other properties and yacht clubs of affluent Cubans and resident Americans. At this time, he was planning the first full-scale confab of American underworld leaders since a Chicago gathering in 1932. It was to be held on the upper floors of the Hotel Nacional in Havana, a busy mecca for gamblers. There were certain decisions to be made at this meeting—one of which had to do with Luciano’s determination to be, as he once put it, “the boss of bosses,” capo di tutti capi, head of the American underworld—and each delegate would have a vote on this matter. During the convention, there would also be banquets, meetings, and parties of the Mafia and its allies, all off-limits to the other guests of the hotel.
The delegates—all known by the FBI to be members of the syndicate and recognized gangsters—began to show up in Havana for this conference. Frank Costello, Augie Pisano, Mike Miranda, Joe Adonis, Tommy “Three Fingers” Brown Lucchese, Joe Profaci, Willie Moretti, Giuseppe (Joe) “the Fat Man” Magliocco, Albert “the Executioner” Anastasia, and Joe “Bananas” Bonanno all arrived from New York and New Jersey. Santo Trafficante came from Florida, Carlos Marcello from New Orleans. Tony Accardo, the head of the Chicago underworld, came with Rocco and Charlie “Trigger Happy” Fischetti (Joe’s brothers). Two other noteworthy delegates would also be present; however, they would not be able to vote on important matters because they were Jewish: “Dandy Phil” Kastel and Meyer Lansky.
As each delegate arrived, he would first go to Luciano’s villa and pay homage to him. After Luciano’s preeminence was acknowledged, each man would give him an envelope stuffed with cash—$150,000 in all—which Luciano would use to buy points in the casino at the Hotel Nacional. Upon the conclusion of these meetings, the delegates were dispatched to the hotel, where thirty-six opulently appointed suites had been reserved for them. Luciano would join them there later, upon the adjournment of the first general meeting of the council of the Unione Siciliana.
The plan Joe Fischetti proposed to Frank Sinatra was that Frank and Nancy meet him in Miami for a February vacation, after which Frank and Joe, Charlie, and Rocco Fischetti would go to Havana and meet Lucky Luciano. (Joe was the best-looking, most charismatic of the Fischettis, though the FBI called him “the least intelligent and least aggressive.”) Frank couldn’t wait to go. As earlier stated, in his old Hoboken neighborhood, thugs like Luciano were revered. He wanted to know what made a guy like Lucky Luciano tick, and he was excited about the opportunity to socialize with such a dangerous and controversial character.
On January 31, 1947, Frank made plans to go to Havana with the Fischetti brothers. He did not—at least from all available evidence—realize that he was going to be attending any sort of underworld confab, nor apparently did he realize that he was being used as a cover for that conference in order to give it an air of legitimacy. Frank just thought he and Nancy were going to Havana to meet Luciano. But unbeknownst to him, Luciano was telling his friends all across the country that one of the perks of coming to Havana for the confab was meeting Frank Sinatra! Or as Luciano’s biographer Martin A. Gosch, author of The Last Testament of Lucky Luciano, explained, “If anyone asked, there was an outward reason for such a gathering. It was to honor an Italian boy from New Jersey named Frank Sinatra, the crooner who had become the idol of the nation’s bobby-sox set.”
Nancy Makes a Decision
At the beginning of February 1947, Nancy Sinatra’s doctor confirmed that she was pregnant again.
While Frank was elated by the news, Nancy wasn’t happy. She no longer trusted Frank and wasn’t even sure she still wanted to be married to him. She also wasn’t sure she was ready to stop fighting for him either. She only knew that she didn’t want to bring a third child into a marriage that she now viewed as fundamentally flawed. Therefore she told Frank she was thinking about terminating the pregnancy.
Frank wasn’t much of a father. Yes, of course he loved his two children, Nancy and Frank. However, he wasn’t exactly available to them. When he had time, he did his best. He played with them, fed them, made them laugh. They loved their daddy, there was no doubt about it. But he rarely had time for them, and when he was home he was usually preoccupied with his work. Frank was a realist about it, too. Throughout his life, he would never flatter himself by saying he’d been a great father. He knew the truth, as did his children. Nancy had accepted his limitations in this regard, but that didn’t mean she was happy about them. The more she and Frank discussed it, the more Nancy was sure she didn’t want to have the baby.
Frank had had strong feelings about abortion ever since his mother was convicted of performing such operations in Hoboken. He was ashamed of what she had don
e, and would never forget the way he was taunted by other kids in the neighborhood after her arrest. Therefore the idea of Nancy terminating her pregnancy was repellent to him. He begged her to reconsider. He suggested that their upcoming trip to Cuba might give them time to sort it all out. However, now Nancy didn’t even want to go to Cuba with him. She would only agree to meet him in Acapulco afterward.
“You will not do it while I’m gone,” Frank told her. It was more like an order than it was a request. However, by this time, Nancy wasn’t taking orders from Frank.
She kissed him goodbye; he went his way—and she went hers, straight to a doctor. “It was hard,” she later told her daughter Tina. “But I knew I was doing the right thing.”
In Cuba with the Boys
On February 11, 1947, Frank Sinatra and the Fischettis flew to Havana and checked into the Hotel Nacional. It took about two days for Frank to come to the realization that he was surrounded by a bunch of known criminals, all of whom wanted his autograph.
Years later, none of Frank’s friends would talk on the record about his visit to Havana that year. However, they remember it well, at least based on what Frank told them privately. Frank suggested that he took a walk on the wild side and found it maybe a little wilder than expected. But once he was there it was too late to do anything about it. Because he had too much pride to leave and believed he would look cowardly or ungracious if he did so, he decided that, what the hell, he was here and might as well have some fun. So he stayed, had a good time, gambled at the casino, went to the races and then to a party with Lucky Luciano, never giving a second thought as to how all of this merriment might appear to his public and his critics. Could he really have been so naïve? It’s not likely, but that was his story . . . and he was sticking to it.
To Martin A. Gosch, Lucky Luciano later confided, “Frank was a good kid and we were all proud of him, the way he made it to the top . . . a skinny kid from around Hoboken with a terrific voice and one hundred percent Italian. He used to sing around the joints there, and all the guys liked him.
“When the time came when some dough was needed to put Frank across with the public, they put it up. He had a job working for Tommy Dorsey’s band, and he was getting about a hundred and fifty bucks a week, but he needed publicity, clothes, different kinds of special music things, and they all cost quite a bit of money—I think it was about fifty or sixty grand. I okayed the money, and it come out of the fund, even though some guys put up a little extra on a personal basis. It all helped him become a big star, and he was just showing his appreciation by coming down to Havana to say hello to me.”
Luciano’s claim would seem to be verification of the underworld’s influence on Sinatra’s early career. But can he be believed? Was Lucky Luciano a credible source for information about Frank Sinatra?
Certainly, if any of the “boys” helped Frank when he was with Tommy Dorsey’s band, it was news to anyone who knew Sinatra well. Ted Hechtman says, “Fifty thousand? That’s what Luciano claims to be responsible for? Well, that makes no sense. Sinatra had friends with money, like Axel [Stordahl]. He would never go to the mob with a favor like that if he needed money, which he didn’t at the time. He was not stupid—impulsive and unthinking, yes, but not stupid.”
Hechtman adds, “And his act? It wasn’t like he had this big production going on with fancy costumes and dancers. He wore one of the same three tuxedos every night.
“And publicity? Before George Evans came into his life, the only publicity Sinatra ever got was whatever Tommy would let him have and whatever Frankie would generate for himself by hounding reporters.
“Song arrangements? Those were Tommy’s arrangements.
“The whole thing is a bunch of crap from a gangster trying to make himself look important.”
True or not, Lucky Luciano’s attempt to take credit for Frank Sinatra’s career in his memoirs helped fuel the sinister stories about Sinatra over the years. But Frank had allowed himself to be in the wrong place at the wrong time with the wrong kinds of people. Of course, Frank’s detractors were inclined to believe Luciano and his ilk, while his fans believed Frank. The rest of the public could only wonder.
Many years later, Frank attempted to explain his presence in Havana this way: He happened to run into Joe Fischetti when he was performing in Miami for a Damon Runyon Cancer Fund benefit. The two spoke and realized that, quite by coincidence, they were both headed for Havana for a vacation. When he got there—he didn’t say with whom he went—he was having a drink and met a large group of men and women. He was invited to dinner with them, and while he was sitting at the table talking it occurred to him that one of the diners was Lucky Luciano. “It suddenly struck me,” Frank said, “that I was laying myself open to criticism by remaining at the table, but I could think of no way to leave the table without creating a scene.” Then, as he explained, he ran into Luciano again at the Hotel Nacional’s casino, “had a quick drink, and excused myself. Those were the only times I have ever seen Luciano in my life.”
A good story, but not true, at least according to all evidence.
However, even Lucky Luciano admitted that Sinatra did nothing actually illegal while in Havana. “I don’t want to give the idea that he was ever asked to do something illegal, by me or by anybody else that I know about,” he said. “He gave out a few presents to different guys, like a gold cigarette case, a watch, that kind of thing, but that was it. As for me, the guy was always number one okay.”
Though Frank tried to ignore the fact that perhaps he had made a blunder in going to the mafioso convention, in the days ahead the media wouldn’t let it go. Robert Ruark, a Scripps-Howard newspaper columnist, wrote a blistering attack on Sinatra, calling him a hypocrite for presenting himself as “the self-confessed savior of the country’s small fry,” yet wanting to “mob up with the likes of Lucky Luciano.”
In fact, the shadow of Frank’s visit to Havana would always loom large; his critics would always think the worst of him because of it. In time, gossip columnists and FBI investigators claimed that he had been carrying $2 million (in small bills!) in a briefcase that he intended to give to Luciano. One of his friends countered, “If you think Sinatra was going to give a deported drug dealer two million bucks, you’re nuts. If you think he would walk around with a briefcase full of that much cash in 1947? Forget it! I know what he had in that briefcase. Clean underwear. That’s what he always carried with him. Clean underwear worth about fifty bucks.” (Moreover, if Sinatra ended up giving Luciano $2 million, he got taken advantage of, because all of the delegates combined only came up with $150,000 for their boss.)7
Regret
After leaving Havana, Frank went to Acapulco to join Nancy for their planned vacation there. He didn’t know she’d terminated the pregnancy until she arrived and then told him. “It was a terrible moment for Dad,” Tina Sinatra recalled.
Frank was devastated by Nancy’s decision. He couldn’t believe she would abort their child. He knew, though, that his bad behavior had been responsible for her decision. He would always regret it. “He had deemed his brief encounters unimportant, but now they had taken from him something dear and irreplaceable,” Tina recalled. “And he told my mother, ‘Don’t you ever do that again.’ ”
Nancy had made her point. She didn’t believe in him, nor did she have faith in their life together. He would have to win favor with her—again. If such a thing was even possible.
The FBI and the Reporter
Frank had known for some time that he was being investigated by the FBI; he’d actually had a difficult time securing a passport for his USO trip with Phil Silvers for that very reason. The FBI made a habit of investigating celebrities at this time, especially with communism a major concern. However, after Frank’s Havana escapade, the Bureau began seriously looking into his association with other underworld characters.
Years later, when FBI documents regarding Sinatra were released under the Freedom of Information Act, Lee Mortimer—Frank’s a
dversary in the press—was revealed to be a primary source of information. In fact, he was FBI associate director Clyde Tolson’s main informant. For instance, Mortimer was the man responsible for the story about Sinatra bringing millions “in small bills” to Havana to lay at the throne of Luciano. This anecdote remains in the FBI records as fact, not rumor. Indeed, the persistent problem with the reams of FBI documents, often referred to in accounts of Frank Sinatra’s ties to the underworld in the 1940s, is that many of them state rumor as fact. Much of it involves stories and anecdotes Mortimer hadn’t even confirmed. In truth, Mortimer and Tolson were simply exchanging gossip about Sinatra.
By this time, 1947, Frank had become tired of Lee Mortimer’s vitriol, especially when word leaked back to him that the reporter might be participating in the FBI’s investigation of him. Therefore, through a mutual friend—a violinist named Joe Candullo—Frank sent Lee a message: “If you don’t quit knocking me and my fans, I’m gonna knock your brains out.”
“I’m not afraid of him,” Mortimer told Candullo. “I’m not going to quit writing about him, either. Tell that to him and his cheap hoodlums.”
“He’s digging into my life? Fine,” Sinatra told George Evans. “I’m digging into his. I think he’s a queer. Find out everything you can about that.” Actually, Mortimer—who would go on to have five wives—was not known to be gay. Still, Frank insisted he was part of what he called “the Garter Belt Mafia.”
George protested, saying he wasn’t a private investigator but rather a publicist. Not only that, he still had to maintain a working relationship with Mortimer; Frank wasn’t his only client. Furthermore, he thought Frank’s idea was mean-spirited and would just lead to more trouble.
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