Frank Sinatra and the Mob

Oct 15, 2009 - by J. D. Chandler - 0 Comments

Frankie and the Boys 1976 - Left to right: Paul Castellano, Gregory DePalma, Sinatra, Tommy Marson, Carlo Gambino, Aladena Fratianno, Salvatore Spatola, Seated: Joseph Gambino, Richard Fusco

Frankie and the Boys 1976 - Left to right: Paul Castellano, Gregory DePalma, Sinatra, Tommy Marson, Carlo Gambino, Aladena Fratianno, Salvatore Spatola, Seated: Joseph Gambino, Richard Fusco

The recent release of Sinatra's extensive FBI file exposes his mob connections in voluminous detail, putting to lie Ol' Blue Eyes' most celebrated claim that he did it his way.

by J.D. Chandler

Rumors of mob connections hounded Frank Sinatra throughout his storied, tumultuous life. His denials were as ready on his lips as his trademark song ''My Way'' became in his waning years. J. Edgar Hoover didn't buy it. He thought Ol' Blue Eyes was a murderer and a Mafioso with a golden voice. Despite Hoover's FBI amassing the largest file on Sinatra of any entertainer in U.S. history, none of the damning information there ever made it to a grand jury. Numerous times the government got close to indicting Sinatra, but it never did. Sinatra had friends in the highest places, first President Kennedy and then President Nixon and finally President Reagan. Each, in different ways and to varying degrees, came to his aid when he most needed them, enabling him to front for the mob with impunity.

Recently the FBI released on its web site all 1,275 pages of Sinatra's FBI file. His file may be viewed at Beginning more than a year ago, the FBI began posting files of scores of other deceased celebrities it had maintained files on to the bureau's web site. There one can read about Charles A. Lindbergh (1,368 pages), Robert Kennedy (1,263), Joseph Kennedy (1,011), President Kennedy (178), Henry Ford (376), Abbie Hoffman (13,262), Martin Luther King Jr. (16,659), Malcolm X (11,674), Nelson Rockefeller (1,472), Cardinal Francis Spellman (536), Marilyn Monroe (80), Jackie Robinson (131), and, of course, the Mafiosi: Al Capone (2,397), Sam Giancana (2,781), and Carlo Gambino (1,239) to name a few.

In the past 25 years, since Congress amended the Freedom of Information Act and passed The Privacy Act, the FBI has grudgingly responded to more than 300,000 Freedom of Information Act requests to release its declassified files. During that time, the FBI has turned over six million pages of FBI documents to the public – mostly news organizations and researchers – in paper format. It would send files to people who filed Freedom of Information requests in writing and who were willing to pay the fees involved. Now, though, the bureau's web site is making posted files available to the public at no charge.

The files the FBI turns over are far from pristine. Some are illegible, some are smeared and almost all have been heavily redacted by FBI agents who went over the files prior to releasing them. The redactions are black marks through names and passages of the file that the agent reviewing the file decides to keep hidden based on various criteria within the bureau's purview. The Freedom of Information and the Privacy acts allow the agent to use any number of security or privacy reasons to redact names and other information from the file. In the case of Sinatra, for example, his name is probably never redacted but the names of stool pigeons or FBI sources used to gather information about him are. Many of the Chairman of the Board's Rat Pack friends received no such kid-glove treatment. Dean Martin, for example, is linked time and again to Sinatra misdoings.

Reading an FBI file, particularly one as voluminous and replete with redactions as Sinatra's, is no easy task. It is largely a mumbo-jumbo of dates, names and incidents, many of them half-baked, wild-goose chases the FBI took in investigating Sinatra. You could easily get the impression that the FBI did not mean to make reading its files an easy chore. (Click here to see a chronological index of Sinatra's file posted on my web site.)

FBI files are an uneven amalgam of fact, rumor, suspicion, allegation, unvarnished gossip, false leads and trivia. Lots of trivia. This is particularly the case in a file as large as Sinatra's.

When the FBI was compiling Sinatra's file it certainly had no intention of ever exposing it to public view. Although there's a dry professionalism to the agents' reports, an antipathy to the crooner permeates the file.

Because the reports in an FBI file were not written for public consumption or scrutiny, they say in an unintended way as much or more about the internal workings of the FBI as they do the famous and infamous subjects investigated. As secret, internal documents the bureau compiles on citizens or groups it either considers a threat to national security or, as in the case of Sinatra, involved in organized crime, the reports in the file allow the agents writing them a free-wheeling opportunity to report whatever they've come up with without the threat of libel. Agents are under no compunction to be fair or even handed or to get both sides of the story. An FBI file on a person does not tell the whole story, nor, in fact, does the file itself form any type of narrative. Overall, it tells a story but not in story form, just in bits and pieces as the reports from the various agents pile up.

Agents use a host of sources in compiling a file. Wiretaps, stool pigeons, personal surveillance, interviews of the subject's acquaintances, neighbors and known enemies, media accounts (gossip columns in particular) and tips gathered from the FBI's hotline. Among all these sources, wiretaps and direct FBI surveillance often provide the most reliable and damning information about a subject under FBI scrutiny. Because the company Sinatra kept included a large number of high-profile mob figures, a veritable who's who of the Mafia from the 1940s on, Sinatra's FBI file includes many references to him gathered in wiretaps of those criminals.

In the 1960s most Americans became aware of Sinatra's friendship with Sam Giancana, the Mafia boss of Chicago. Most people were unaware of the connections of Sinatra's family and the help he received from mobsters in his career. His FBI files definitively show that Sinatra was up to his ears in mob-related schemes and activities throughout his entire adult life.

Sinatra's connection with mobsters actually began at birth. His uncle, Babe Gavarante, was a driver for a gang of armed robbers and may have been connected to the organization Willie Moretti ran in Bergen County and northern New Jersey. Gavarante, the brother of Sinatra's mother, was convicted of murder in 1921 in connection with an armed robbery in which he had driven the get-away car. He was sentenced to 15 years at hard labor.

One persistent rumor held that Sinatra was distantly related to Al Capone. Whether he was a cousin of Big Al, or not, Sinatra did have a life-long relationship with the infamous Fischetti brothers. Charles, Joseph and Rocco Fischetti were cousins of Capone and well-know gangsters in their own right.

The Fischetti Brothers

Charles ''Trigger Happy'' Fischetti, called a notorious ''Chicago gangster'' in the FBI files, was the mob's political fixer in Chicago. He and Sinatra were known to be close friends as early as the 1940s.While Charles Fischetti was under FBI surveillance in 1946 he and Sinatra visited Fischetti's mother in Brooklyn for three hours. Sinatra also helped Fischetti get tickets to sports events several times. Sinatra helped Fischetti set up a string of auto dealerships, by lending his name to the enterprise and doing commercials free of charge. (Sinatra did receive at least two Thunderbirds that became the property of Sinatra Enterprises.)

Joseph Fischetti, also known as a ''Chicago gangster,'' but better known for his activities in Miami, especially in connection with the Fontainbleu Hotel, was one of Sinatra's closest friends in the 1940s. FBI surveillance of Fischetti shows that he and Sinatra kept in weekly telephone contact for an extended period. They met in person several times in New York and Miami.

Sinatra was Joseph Fischetti's houseguest in Miami in February 1947 when they traveled to Havana in the company of Joseph's brother, Rocco, who was in charge of Chicago gambling and was a notorious woman-beater. On this infamous trip Sinatra met with Charles ''Lucky'' Luciano. Rumors about this meeting dogged Sinatra for the rest of his life.

Sinatra and Joseph Fischetti remained friends for years. Sinatra performed many times at the Fontainbleu Hotel in Miami. Fischetti was deeply involved with this hotel. As early as May 1947 Fischetti had bragged to an FBI informant about his ''financial interest'' in Frank Sinatra. Fischetti worked as a sort of agent for Sinatra in Miami and Chicago and got him several bookings in the early 1950s when Sinatra's career was nearly dead.

Fischetti's financial interest nearly came to light in 1963 when the IRS investigated the so-called ''Fontainbleu Complex.'' This investigation revealed that Sinatra performed ''without charge'' at the Fontainbleu and that Joseph Fischetti, who was being paid more than $1,000 per month to arrange Sinatra's performances, gave him expensive pieces of jewelry instead of cash. This story came to light again during Nevada Gaming Commission hearings in 1981. Again the charges were never proved.

Willie Moretti

Family connections led to another major underworld link that was very important to Sinatra's career. Nancy Barbato, Sinatra's first wife, was a cousin of a ''key member of Willie Moretti's mob,'' as the FBI report put it. Moretti controlled gambling and other rackets in Bergen County and northern New Jersey and was a known associate of Frank Costello, the New York Mafia boss.

After Sinatra's marriage to Nancy Barbato, Moretti (a.k.a. Willie Moore) took an interest in the young singer's career. He arranged several singing engagements for Sinatra, giving his career a large boost. Moretti also set an example for other mobsters who would later befriend Sinatra. Sinatra several times denied that Moretti helped his career. Columnist Lee Mortimer's allegations concerning Moretti led to Sinatra assaulting Mortimer. Sinatra's private testimony to the Kefauver Committee, on March 1, 1951, tells the true story, ''Well, Moore, I mean Moretti, made some band dates for me when I first got started….''

In 1948 Moretti told undercover FBI agents that he had an ''association'' with Sinatra. Later that year an informant told the FBI that both Sinatra and comedian Lou Costello ''kicked in'' to Moretti. In 1949, when Sinatra separated from his wife and was seen in public with Ava Gardner, Moretti sent him a telegram urging him to return to his wife.

Moretti testified openly, maybe too openly, to the Kefauver Committee, admitting that he was a gambler. Ten months later he was gunned down in Joe's ElbowRoom in Cliffside Park, N.J. Later, when Mario Puzo's book, The Godfather, came out it was widely rumored that one of the characters was based on Sinatra and that Don Corleone was partly based on Willie Moretti.

Tommy Dorsey always denied that he had been threatened in order to release Sinatra from his long-term contract; it is fairly certain that movie mogul Harry Cohn never found a horse's head in his bed. But Sinatra did sing at the wedding of Moretti's daughter in 1948, and he clearly had a great deal of affection for his neighbor and benefactor, Willie Moretti. Moretti, in return, took a great interest in Sinatra's career and helped him wherever he could.

Sam Giancana

Sinatra's most enduring, and well known, association with a mobster was with Sam ''Momo'' Giancana. Giancana started out as a thief and killer in Chicago in the 1920s. He was arrested for murder in 1926, but was not prosecuted because the state's case fell apart when Alexander Burba, a cab driver and the main witness, was murdered. Giancana was rumored to be the driver and a gunman at the 1929 St. Valentine's Day Massacre. He spent a good part of the 1920s and 1930s in prison for various crimes.

By the late 1940s Giancana was closely associated with Anthony ''Tony Batters'' Accardo, an ex-bodyguard of Al Capone and rumored to be one of the gunmen in the Saint Valentine's Day Massacre. By the late '50s Giancana had risen to the top of the heap in Chicago. There he controlled protection, pinball, prostitution, numbers, narcotics, loan sharking, extortion, counterfeiting and bookmaking. He was arrested over 70 times, three times for murder.

In consolidating his power Giancana ordered the deaths of over 200 people, some of whom were tortured to death. These killings brought him to the head of an international crime empire, which included interests in the Riviera, Sands and Desert Inn hotels in Las Vegas estimated by the FBI to generate over $2 billion in income annually. Some $40-$50 million of that went directly to Giancana.

Giancana liked to be around entertainers and he had several of them for friends including Joe E. Brown, Jimmy Durante, Dean Martin, Keeley Smith, and Phyllis McGuire (of the McGuire Sisters). It was Frank Sinatra's sapphire friendship ring that Giancana wore every day, though. Giancana was often annoyed by the attention Sinatra generated and thought he had a ''big mouth,'' but he was a regular at Sinatra's legendary parties. Giancana often visited Sinatra in his dressing room at the Sands Hotel and at the Fontainbleu in Miami.

According to FBI files, the autobiography of Antoinette Giancana and the testimony of Johnny Roselli to the U.S. Senate Church Commission in 1975, it was Giancana, along with a few other mobsters, who conspired with the CIA to assassinate Fidel Castro in the early 1960s. Giancana also had the distinction of sharing a mistress, Judith Campbell, with President John F. Kennedy. Sinatra introduced her to both men. Giancana is often named as a suspect by people who believe the Mafia assassinated President Kennedy. Giancana was murdered in 1975 after his role in the Castro plot came to light, but before he could testify at congressional hearings investigating the CIA.

For a good part of his life Giancana was under constant FBI surveillance. At one point Giancana got a court order to make his FBI tail stay two foursomes behind him on the golf course. This surveillance extensively documents the relationship between Giancana and Sinatra.

Sinatra told IRS investigators in 1959 that he met Giancana at the Fontainbleu Hotel in March 1958. Sinatra always maintained that he and Giancana were friendly, but not close, and that they had no business relationship. The FBI surveillance shows this to be a lie.

Sinatra played a kind of court-jester role for Giancana, giving command performances when asked. Sinatra also arranged command performances by other entertainers for Giancana, especially at Giancana's Wheeling, Ill., nightclub, the Villa Venice Supper Club, a front for an illegal-gambling operation. Sinatra arranged several shows there featuring himself, Dean Martin, Sammy Davis Jr. and Eddie Fisher. The performers at these shows worked gratis.

On at least one occasion, in October 1962, Eddie Fisher was coerced into making an appearance at the Villa Venice. Fisher had just finished a successful engagement in New York City and had planned a long run at the Desert Inn in Las Vegas.

Giancana decided that he wanted Fisher for the re-opening of his club on Halloween. Fisher, his agent and Moe Dalitz, the operator of the Desert Inn, were against changing Fisher's plans. Fisher and his agent thought it could hurt his career. None of them, however, had the courage to turn down Giancana. It was arranged for Fisher to split his engagement at the Desert Inn so he could appear at the Villa Venice.

After the arrangements were made Giancana changed his mind and decided he wanted Fisher for a three-week engagement. Fisher voiced his reluctance to Sinatra, who said (according to an FBI report), ''Look, you're going over there for 18 days. Never mind about the Desert Inn, I already handled that. I take care of that. They do what I tell them.'' The FBI estimated, based on overheard conversations, that the Villa Venice reopening, and gambling at the nearby Quonset Hut, grossed over $3 million.

As for the business relationship between Sinatra and Giancana, nothing was ever clearly proven. The most consistent allegation is that Sinatra acted as a front for Giancana's ownership of the Cal-Neva Lodge in Lake Tahoe in the early '60s. Giancana was included in Nevada's ''Black Book'' that listed the 11 men who were not allowed into any Nevada gambling establishment, so his ownership of any gambling interests there had to be covered up.

In 1960 Giancana made arrangements to buy the Cal-Neva Lodge, located at the north end of Lake Tahoe exactly on the California-Nevada border. The owners of record would be Frank Sinatra, Hank Sanicola (an old friend and business partner of Sinatra's) and Dean Martin. At first Sinatra owned one-third of the hotel, but within a couple of years his ownership had risen to over half and Dean Martin had dropped out in favor of Sanford Waterman. Paul ''Skinny'' D'Amato, one of Giancana's lieutenants who had ''worked'' the West Virginia primary for John Kennedy, took over day-to-day operation of the club.

The Cal-Neva Lodge, with its unique location half in California and half in Nevada, was perfect for Giancana's purposes. He visited the club regularly (when he would admit visiting he claimed that he always stayed on the California side) for trysts with his mistress, Phyllis McGuire, meetings with other mobsters or Sinatra's wild parties. Giancana's visits made Hank Sanicola, who had invested $300,000 of his own money, nervous because federal agents often accompanied Giancana. Sinatra told Sanicola not to be a ''worrier''.

Giancana's ownership of the hotel was confirmed by the FBI, which recorded a conversation between Giancana and Johnny Roselli (his representative in Las Vegas), in which Giancana said, ''I am going to get my money out of that joint (Cal-Neva) and end up with half of it with no money.''

For Sinatra, the Cal-Neva Lodge was cursed. After a heated spat with Ava Gardner there in 1951, Sinatra took an overdose of sleeping pills. He later denied that he had tried to kill himself, but in 1985 George Jacobs, Sinatra's longtime valet, told Kitty Kelley: ''Thank God, I was there to save him. Miss G was the love of his life, and if he couldn't have her, he didn't want to live no more.'' Gardner would become Sinatra's second of four wives; he later would marry Mia Farrow and Barbara Marx. His three children, Nancy Jr., Frank Jr. and Tina were born to his first wife.

In 1962 Federal Agents investigated a prostitution ring that was run openly through the registration desk. A few weeks later an attempt was made on the life of one of the employees in front of the hotel. Shortly afterward Marilyn Monroe took an overdose of sleeping pills there. She was saved, but died a few days later in Los Angeles. That same summer ex-Deputy Sheriff Richard Anderson had a fight with Sinatra at the Cal-Neva Lodge, a few days later Anderson died in a mysterious car accident. Many people, including J. Edgar Hoover, suspected Sinatra of having Anderson killed, but nothing was proved.

The next summer, during a singing engagement at the Cal-Neva by the McGuire Sisters, Phyllis McGuire, Sam Giancana, Frank Sinatra and Victor LaCroix Collins, road manager for the McGuire Sisters, became involved in a brawl in Giancana's bungalow. FBI agents witnessed the fight and informed the Nevada State Gaming Commission. This was the last straw and in August 1963, Ed Olson, chairman of the commission started an investigation with the goal of revoking Sinatra's gaming license.

Sinatra used all of his power and prestige to fight the charges against him. When he addressed the General Assembly of the United Nations he made a joke about his ''used casino.'' President Kennedy even interceded on his behalf, asking Nevada Gov. Grant Sawyer during a Las Vegas motorcade why he was ''being so hard on Sinatra.'' In the end the case was too convincing against Sinatra and he voluntarily gave up all his interests in Nevada casinos, which included interests at the Sands and Desert Inn as well. He was still allowed to perform in Nevada, but it was not until 1981 that he managed to obtain a new gaming license.

Sinatra's relationship with Giancana, coupled with his own unruly temper, gave him a reputation for being dangerous. On more than one occasion people who had angered Sinatra received threatening phone calls saying that Giancana would ''teach them a lesson.'' The most blatant example of this came in 1966 when comedian Jackie Mason angered Sinatra by making jokes about his marriage to Mia Farrow. Mason received phone calls threatening his life, but refused to change his routine. Six days later three bullets were fired through the glass door of Mason's hotel room in Las Vegas. The Clark County Sheriff's Department investigated, but dropped the case because it said there was no motive for the shooting.

Mason stopped making his jokes about Mia Farrow, but continued to make cracks about Sinatra in his show. A few weeks later, at an appearance in Miami, Mason quipped, ''I don't know who it was that tried to shoot me…After the shots were fired all I heard was someone singing: Doobie, doobie, do.'' Mason received four death threats that week with warnings that he should stop talking about Sinatra.

On Feb. 13, 1967, while Mason was sitting in a car in front of an apartment building in Miami, a man wearing brass knuckles yanked open his door and smashed Mason in the face, breaking his nose and crushing his cheekbone. ''We warned you to stop using the Sinatra material in your act,'' the attacker said before leaving. Mason finally got the message and stopped using jokes about Sinatra.

After Giancana's semi-successful lawsuit against the FBI, in 1963, the publicity around him began to seem dangerous to Tony Accardo and Paul Ricca, the real Mafia powers in Chicago. When Giancana was jailed for contempt of court in 1965, that was the end of his power. After his release he was exiled in Mexico for the rest of his life.

Benjamin ''Bugsy'' Siegel

Frank Sinatra was physically a small man. At his local draft board physical in 1943, the 5'71/2''-teen idol weighed in at 119 pounds. (He flunked the physical due to a perforated left eardrum.) Sinatra idolized the strong and the tough. Since boyhood he always wanted to be around the strongest and the toughest men he could find. This led to his strong attraction to both boxers and gangsters. One FBI informant said it was well known that Sinatra had a ''hoodlum complex''.

According to Eddie Fisher, Sinatra once said, ''I would rather be a Mafia don than president of the United States.'' According to Jo-Carroll Silvers, wife of comedian Phil Silvers (a good friend of Sinatra's), ''Phil and Frank adored Bugsy (Ben) Siegel…They were like two children seeing Santa Claus…They were so wide-eyed and impressed with this man…They would brag about Bugsy, what he had done and how many people he had killed… I will always remember the awe Frank had in his voice when he spoke about him (Siegel). He wanted to emulate Bugsy.''

Benjamin ''Bugsy'' Siegel was the representative of Meyer Lansky and Lucky Luciano in Los Angeles from 1934 until his death in 1947. He was known as one of the original members of the legendary, and some say fictional, Murder Inc. Siegel was also one of organized crime's pioneers in Las Vegas, building the Flamingo Hotel which opened on Christmas Eve 1946. Sinatra and Siegel had a nodding acquaintance, but there is no evidence that there was anything more than that.

Mickey Cohen

The relationship between Sinatra and Mickey Cohen is well documented. Cohen was a Siegel lieutenant who made himself an underworld power after Siegel's death. Cohen, a Jew, was never a ''made guy'' (a member of La Cosa Nostra), and he had constant battles with Jack Dragna, the official Mafia boss of Los Angeles, but he remained a powerful crime figure all through the 1950s and well into the 60s.

Cohen and Sinatra were fairly close friends. Sinatra visited him at his home in 1948, even though Cohen warned him that he was under constant surveillance, to ask him to have Johnny Stompanato, Cohen's bodyguard, stay away from Ava Gardner. Cohen told him that he never mixed in between men and their ''broads'' and that Sinatra should go back to his wife and kids. ''I talked to him like a friend,'' Cohen stated later in his autobiography.

Cohen, like the other mobsters who knew Sinatra, used him for his star power. On at least one occasion Cohen called Sinatra and asked him to meet with a business associate from Ohio and his 14-year-old daughter. Sinatra didn't rush over to Cohen's house, as Cohen wanted, but he did invite them to a radio broadcast where all three were allowed to sit on the stage.

James Tarantino and Hollywood Nite Life

Through Cohen Sinatra got involved with James Tarantino and his blackmail/scandal sheet, Hollywood Nite Life. Tarantino, an ex-sportswriter who had known Sinatra from the New York boxing scene in the early '40s, used the tabloid in a blackmail scheme. He would dig up dirt on Hollywood celebrities and then threaten to publish his information if the stars didn't advertise with him.

Columnist Westbrook Pegler called Tarantino, who had been a member of The Varsity (a group of Sinatra's friends that was a forerunner of the later Clan or Rat Pack), a protégé of Sinatra. According to Tarantino, who was later convicted of extortion, he and Hank Sanicola started Hollywood Nite Life in 1945. Sinatra, he said, had put up $15,000 to get the magazine started.

In his private testimony to the Kefauver Committee, in 1951, Sinatra gave a different version of the story:

Q: We have information to the effect that you gave Tarantino quite a large sum of money to keep him from writing a quite uncomplimentary story about you.

A: Well, you know how it is in Hollywood…Jimmy called up and said he had an eyewitness account of a party that was supposed to have been held down in Las Vegas in which some broads had been raped or something like that. I told Jimmy that if he printed anything like that he would be in a lot of trouble.

Q: Did he ask you for money?

A: Well, I asked Hank Sanicola, my manager, to handle it and that was the last I heard of it…

Q: Did Hank tell you he paid Tarantino?

A: Well, I understand Tarantino was indicted and I don't know the rest of the story, but the Hollywood Nite Life quit publishing this crap afterward.

Another version of the story, retold in Kelley's book His Way, was that Mickey Cohen asked Sinatra for $5,000, on three separate occasions for a total of $15,000, to suppress articles in Hollywood Nite Life. Whether Sinatra was blackmailed by his ''friend,'' Cohen, his ''protégé,'' Tarantino, or he voluntarily gave money to support the magazine, he did advertise with Tarantino and he always got good publicity in Hollywood Nite Life.

Charles ''Lucky'' Luciano

Charles ''Lucky'' Luciano was one of the most powerful and influential Mafia bosses in American history. He is considered by some to be the real winner of the Castellammarese War of 1930, which led to the formation of New York's Five Families. After his brief war with Sal Maranzano in 1931, in which he earned his ''Lucky'' nickname, Luciano consolidated his power by forming the Commission.

The Commission was a group of heads of Mafia families that met regularly to work out inter-family problems. The Commission was designed to save the mob from autocratic rule by dictatorial bosses and internecine warfare. It worked for a while, but its main effect was to increase Luciano's power. Luciano became so powerful, in fact, that he was the main target of New York D.A. Thomas Dewey, who built his political reputation by prosecuting top mobsters.

In 1936 Dewey successfully convicted Luciano of controlling prostitution in New York. At the end of World War II, Luciano was released from prison and deported to Italy.

In 1946 Luciano traveled to Cuba in an effort to reassert his power over the American mob. All of the most prominent underworld leaders traveled to pay their respects to Luciano at the famed ''Havana Conference.'' It looked as if Luciano would be able to hang onto his position and rule the mob from Havana.

Sinatra made at least two trips to Havana to meet Luciano. One trip was over Christmas 1946. Sinatra performed on Christmas Eve at a party held in his honor by Luciano. This party came during a break in a meeting that decided the fate of Siegel, who was killed a few months later. The second trip, over a four-day weekend in February 1947 is documented in Sinatra's FBI file. He traveled to Havana with Joseph and Rocco Fischetti. They stayed at the Hotel Nacional and all three met with Luciano on more than one occasion.

This trip was widely reported in the media and it caused Sinatra problems the rest of his life – both with the public and the underworld. That trip would later lead to allegations that Sinatra delivered $2 million in cash to Luciano.

Joseph ''Doc'' Stacher, who ran Meyer Lansky's operation in New Jersey at the time and later ran the Sand's Hotel, remembered the Havana meeting years later in an interview quoted in Kitty Kelley's His Way: ''The Italians among us were all very proud of Frank. They always told me they had spent a lot of money helping him in his career ever since he was in Tommy Dorsey's band. Lucky Luciano was very fond of Frank's singing. Frankie flew into Havana with the Fischettis, with whom he was very friendly, but of course, our meeting had nothing to do with hearing him croon…Everyone brought envelopes of money for Luciano …But more important, they came to pay allegiance to him.''

It is likely that Sinatra also gave an envelope of cash to Luciano, but it is far-fetched that he carried $2 million in his briefcase for him, as it was later charged. As Sinatra said in his 1981 NSGC hearing, ''Show me a briefcase that will hold $2 million in cash and I'll give you the money.''

Shortly after the February meeting Robert Ruark, a New York columnist, wrote an article about Sinatra's visit to Luciano. The U.S. government put pressure on Cuba to deport Luciano to Italy. Many mobsters thought that it was Sinatra's bragging about meeting Luciano that led to his deportation. This led to Sinatra's reputation as a ''big mouth''.

Luciano knew better. According to organized-crime historian and writer Allan May, Luciano believed that Vito Genovese had informed on him by telling Harry Anslinger of the Narcotics Bureau that Luciano was in Havana. (See ''Havana Conference - 1946'', by Allan May.)  Sinatra and Hank Sanicola later visited Luciano in Naples, Italy, where Sinatra presented him with a gold cigarette case engraved: ''To my dear pal Charlie, from his friend Frank.'' The cigarette case and a piece of paper bearing Sinatra's unlisted telephone number were found on Luciano when Italian police searched him in 1949.

Frank Costello

Frank Costello was acting boss of what later became known as the Genovese family during Luciano's incarceration and exile. In 1947 he became the boss, but spent the next 10 years feuding with Vito Genovese for control of Luciano's empire. In 1957 he was shot and wounded by Vincent ''Chin'' Gigante. Costello subsequently retired in favor of Genovese.

Many rumors and reports of Sinatra's connection with Costello exist, but there is very little evidence to back them up. Sinatra and his sycophant group, The Varsity, spent a great deal of time at boxing matches at Madison Square Garden in the early 1940s. Frank Costello was known to hang out there as well, so it is very likely that they met.

Costello was known to be the padrino of Willie Moretti so it is possible that he also took an interest in Sinatra's career. Costello owned the Copacabana nightclub in New York and always attended Sinatra's engagements there. Costello was believed to be the true owner of the Sands Hotel in Las Vegas, in which Sinatra also had a part ownership. The San Francisco police also believed Costello to be the true owner of Hollywood Nite Life.

Columnist John Miller is quoted, in Kitty Kelley's biography of Sinatra, as saying, ''Sinatra and Frank C. were great pals. I know because I used to sit with Frank C. at the Copa and Sinatra would join us all the time. He was always asking favors of the old man, and whenever Sinatra had a problem he went to Frank C. to solve it.'' Miller was making the point that Costello secured the role of Maggio in From Here to Eternity for Sinatra. While it is highly likely that Sinatra asked for Costello's help in this, and Harry Cohn, of Columbia Pictures, had as many mob ties as Sinatra, it is also clear that it was Sinatra's own efforts, with an assist from Ava Gardner, that got him that role.

There are several rumors in Sinatra's FBI file that Sinatra was ''brought up'' by Costello and that Costello put pressure on Willie Moretti to help Sinatra. Again there is no proof behind these rumors and, knowing Sinatra's connection to Moretti, it is more likely that Moretti gave Sinatra an ''in'' with Costello, than the other way around.

Las Vegas

No performer was more associated with Las Vegas than Frank Sinatra. His affiliation with several hotels in Las Vegas brought him into contact with a wide variety of mobsters.

The Sands Hotel

In 1954 Sinatra obtained a Nevada gaming license and bought a 2 percent interest in the Sands Hotel. Later Vicente ''Jimmy Blue Eyes'' Alo gave him a gift of an additional 7 percent of the hotel. Sinatra remained associated with the Sands until 1967, although he gave up his ownership in 1963 in the Cal-Neva/Warner Bros. deal, eventually rising to vice president of the corporation and earning $100,000 per night when he performed. Among the perks he received at the hotel was free no-limit gambling in the casino.

The Sands Hotel was a joint enterprise run by the Genovese family and the Chicago Outfit. Many mobsters were associated with the hotel including:

  • Joseph ''Doc'' Stacher – the No. 1 man who ran the hotel and who was closely associated with Meyer Lansky. Stacher had a long police record that included arrests for assault and battery, robbery, larceny, bootlegging, hijacking and murder. He was also a very close friend of Sinatra.

  • Charles ''Babe'' Baron – the official greeter at the hotel, he had previously been a suspect in a murder.

  • Joe Fusco – of the old Capone mob.

  • Meyer Lansky – The highest ranking non-Italian member of ''The Syndicate.'' Lansky had been closely associated with Charles ''Lucky'' Luciano, and, since his teen years, had partnered with Benjamin ''Bugsy'' Siegel.

  • Abner ''Longy'' Zwillman – an early member of Irving ''Waxy Gordon'' Wexler's bootlegging operation in New Jersey. He later was a partner with Willie Moretti and was closely associated with Meyer Lansky.

  • Anthony ''Tony Batters'' Accardo – former bodyguard of Al Capone and power behind the Chicago throne from 1943 until his death in 1992.

  • Gerardo Catena – acting boss of the Genovese family.

  • Abraham Teitelbaum – former attorney of Al Capone.

  • John Roselli – Giancana's representative in Las Vegas. He had been involved in the early '60s plots against Fidel Castro. In 1963 Sinatra sponsored Rosselli for membership in the Friar's Club, where Roselli was later charged with running a gambling operation. Roselli moved to Miami after Giancana's removal from Chicago. In 1975 Roselli testified to the U.S. Senate's Church Commission about links between the Mafia and the CIA. Shortly after his testimony his dismembered body was found in an oil drum floating in Biscayne Bay.

In 1967 Howard Hughes purchased The Sands Hotel. Frank Sinatra negotiated a new contract with the mob-owned Caesar's Palace and broke his contract with the Sands. The breaking of The Sands' contract was a memorable Sinatra tantrum in which he trashed the lobby and pool before having two teeth knocked out by casino manager Carl Cohen.

Desert Inn

Sinatra appeared at the Desert Inn many times from the early 1950s until Howard Hughes purchased it in 1967. A group of mobsters, mostly from Cleveland, owned the Desert Inn. Meyer Lansky and Sam Giancana also had interests in the hotel. Moe Dalitz, a close friend of Sinatra, ran it. Dalitz helped keep Sinatra employed when his career hit a low point after 1949.

In the 1920s and 1930s, Dalitz was a bootlegger from Cleveland, aligned with the Italian Mayfield Road Mob.

At the Desert Inn Sinatra was known to hang out with people such as Benny Macri, who was suspected of being the killer of a union organizer in New York. Macri was not convicted of this crime, although he had a reputation as a killer in the underworld. He was also pals with Aladena ''Jimmy the Weasel'' Fratianno, an enforcer and executioner for Jack Dragna in Los Angeles. Later Fratianno would be acting-boss of the LA crime family and he was involved in the Westchester Premier Theater scam with Sinatra, detailed later. Fratianno eventually became a celebrated informer for the FBI.

Caesar's Palace

The origin and ownership of Caesar's Palace in the 1960s is shadowy, but, like the other Las Vegas casinos that Sinatra was associated with, Caesar's employed several people with ties to organized crime. Two in particular were Eugene Cimorelli, the casino's official greeter. He was an associate of Chicago gangster Anthony ''Tony the Ant'' Spilotro and golf partner of Anthony ''Tony Batters'' Accardo, the behind-the-scenes boss of Chicago. The other was Sanford Waterman, who had previously been one of Sinatra and Giancana's partners in the Cal-Neva Lodge. Waterman was later convicted of racketeering.

In 1970 the IRS began an investigation of operations at Caesar's Palace. During the investigation it became evident to investigators that Sinatra was scamming cash from the casino by cashing in chips that he had received for free. When Waterman, the casino manager, was informed of this he confronted Sinatra inside the casino. Typically, Sinatra reacted violently. The men exchanged ethnic slurs. When Sinatra became violent Waterman pulled a gun and pointed it at Sinatra's head, ending the fight. Assault charges were dropped against Waterman because there were visible marks on his throat where Sinatra had been holding him.

After the fight with Waterman, Sinatra vowed never to set foot in Nevada again. He returned in 1973, after Waterman was arrested on racketeering charges and Caesar's Palace offered him $400,000 per week (a record for Las Vegas performers at the time) and a free bodyguard.

In 1980 Sinatra forced Caesar's Palace to list him as a key employee so he could apply for a new Gaming License. He said that he wanted to clear his name from charges that led to his license being pulled in 1963. Sinatra paid $500,000 for an investigation of his past and used all of his connections and power (including the support of President Ronald Reagan) to influence the outcome of the NSGC hearings.

At the hearings, that took place over several months in 1981, Sinatra lied repeatedly about his activities and relationships with criminals and mobsters. In the end he was granted a Nevada Gaming License once again. ''We got that junk behind us. We cleared the air,'' he said.

Carlo Gambino

Carlo Gambino was a member of the New York crime family that was headed by Albert Anastasia and later became known as the Gambino family. He was involved in the 1957 plot, with Vito Genovese and Thomas Lucchese, that brought Genovese and Gambino to power in their respective families.

Gambino, Genovese and Lucchese fought an on-and-off war with Joseph Bonnano, the head of the Bonnano crime family. Bonnano steadily lost ground as he lost allies: Albert Anastasia was murdered in 1957 and Joe Profaci died in 1962. Men whose allegiance was to Gambino replaced each. By 1967, when Vito Genovese died, Gambino was left as a near boss-of-bosses. Gambino is known for running one of the most profitable crime families in history and for never having gone to jail. He remained in control of his family, with help from Paul Castellano, until his death in 1976.

It is not clear when Sinatra first became associated with Gambino. Sinatra was involved in at least two business deals with Gambino in the 1970s. Gambino also appeared in the famous photograph taken in 1976 at the Westchester Premier Theater (one of their joint enterprises) along with Paul Castellano, Gregory De Palma, Thomas Marson, Aladena Fratianno, Salvatore Spatola, Joseph Gambino and Richard Fusco.

The business deals that Gambino and Sinatra were involved in together were:

Computer Fields Expressway – In 1970 Jack Pourtney, a stock broker at the 1st Williams Street Corporation in New York City, approached Richard Alpert about investing money in a company called Computer Fields Expressway. Alpert went to an acquaintance known to him as Joe Paris, real name Joseph Guarnera, to help him raise money to invest.

Paris, who claimed to be a relative of Carlo Gambino, raised $100,000 allegedly from Gambino, Sinatra and Jilly Rizzo (a long-time friend and occasional bodyguard of Sinatra). The stock price for CFE dropped from $12 per share to $.75 per share. According to the FBI file the drop in the stock price was because Pourtney was stealing assets from the underwriting company, 1st Williams St. Corp.

The FBI became involved, at the request of the U.S. attorney in New York, when Alpert charged that his life was threatened if he didn't return the $100,000. By this time the Securities and Exchange Commission had become involved with the investigation and Pourtney cooperated with them.

In February 1971, Alpert was subpoenaed to appear before a federal grand jury. He took the Fifth Amendment and refused to answer any questions. In March 1971, FBI agents questioned Alpert. He denied that his life had been threatened. He also denied that Frank Sinatra or Carlo Gambino had ever invested money in CFE.

Based on other deals that Sinatra was involved in it is likely that he invested money with Gambino in CFE. Whether Sinatra or Gambino invested the money in CFE, it is probable that Sinatra had no knowledge of or participation in the threats or the attempts to extort money from Alpert.

Westchester Premier Theater – The Westchester Premier Theater in Tarrytown, N.Y., began as a scheme by Gregory De Palma and Richard Fusco, members of the Gambino family. First there was an inflated stock scam, where stock was sold to ''big names'' such as Alan King, Steve Lawrence and Eydie Gorme for pennies on the dollar. The stock never drew much interest and there were several phony purchases and corporate purchases with kickbacks to executives. As a result the stock dropped to around $1 per share.

The theater was built, with huge construction cost overruns, on a landfill owned by De Palma and Fusco in 1974. De Palma and Fusco, needing more money to keep their scheme afloat, convinced Carlo Gambino to invest $100,000. He did so only on the condition that Frank Sinatra be brought in on the deal. The theater opened in 1975 with a performance by Diana Ross who was paid $235,000. Fusco and De Palma ran the theater as if it were a Las Vegas casino, skimming huge amounts from concessions and t-shirt sales and selling tickets for seats that didn't exist.

The theater was huge and very well appointed. The biggest acts in show business were booked there and the gross for the first year was estimated at $5.3 million. But by December 1976 the theater was near bankruptcy. Only a run of performances by Sinatra and Dean Martin in May 1977 delayed the closing of the theater.

Federal agents, investigating another matter, tapped the phone of Tom Marson, a friend and Palm Springs neighbor of Sinatra. They recorded a conversation between Marson and De Palma in which they discussed skimming cash from the upcoming Sinatra appearance at the Westchester Premier Theater. The result of this conversation was 10 indictments handed down by a New York Grand Jury in June 1978. During the investigation it came out that Sinatra was paid $50,000 ''under the table'' for his first appearance there. Sinatra was never indicted.

Raymond Patriarca

Raymond Patriarca was the crime boss of Providence, R.I. In the early 1950s he moved in on organized crime in Boston and by 1954 had control of all of New England. There are many rumors about Patriarca's connection with both Joseph P. Kennedy and Frank Sinatra. One rumor that is stated more than once in the FBI files is that Patriarca introduced Sinatra to organized crime figures in New York. From Sinatra's history with Willie Moretti, Frank Costello and others it is clear that this rumor is absurd.

In 1963 Sinatra invested $55,000 in the Berkshire Downs Racetrack in western Massachusetts. He and Dean Martin were named directors of the track. Rumors abounded, and were often repeated in the FBI files, that Sinatra was a front for the real owners of the racetrack: Raymond Patriarca and Gaetano ''Three-finger Brown'' Lucchese. The track went bankrupt in 1965, but the deal came back to haunt Sinatra years later.

In 1972 the House Select Committee on Crime prepared a subpoena for Sinatra to question him about the Berkshire Downs Racetrack. A phone call from Sen. John Tunney of California, for whom Sinatra had raised $160,000 during his re-election campaign, stopped the subpoena. Tunney informed the committee, after talking with Mickey Rudin, Sinatra's lawyer, that Sinatra would be glad to appear before them if he were invited.

The committee obligingly invited Sinatra to appear on June 4, 1972. Instead Sinatra flew to England. Incensed the committee prepared a second subpoena and ordered U.S. marshals to stand by at all ports of entry to issue the subpoena as soon as Sinatra re-entered the United States. Sinatra called in some favors and after telephone calls from Vice President Spiro Agnew, a close friend of Sinatra, the second subpoena was cancelled and a new invitation was issued for July 18. In addition the committee agreed to limit their questions to the Berkshire Downs Racetrack.

Sinatra took a belligerent attitude with the committee when he appeared. He also apparently lied several times. For example:

Q: Tell us about the first contact you had with anyone in relation to Berkshire Downs?

A: The first and only contact I had was with a man named Sal Rizzo.

Q: How did you know Mr. Rizzo?

A: I met him.

Q: How?

A: I can't remember where or how, but I met him and we got to talking about it and I liked his idea for the investment.

Later Charles Carson, the racetrack controller, would testify that Rizzo and Sinatra were childhood friends. Rizzo had told him that, ''I have known Sinatra since New Jersey. I was a neighbor of his and I knew the whole family.''

When Rizzo appeared in front of the committee he took the Fifth Amendment on 34 of the 46 questions he was asked, refusing to say anything about his relationship with Sinatra, or even if he had lived in New Jersey. Testimony Rizzo had given to the Florida Beverage Control Commission (FBCC) in 1968 was read into the record in which Rizzo testified that Sinatra had received money from Berkshire Downs and that Rizzo had known Sinatra for ''fifteen to twenty years.''

Commenting on Sinatra and Rizzo's testimony, the committee counsel said, ''It appears … that Mr. Sinatra's testimony … was false, or the testimony of Mr. Rizzo before the [FBCC] was false. In either case one of the gentleman has committed perjury.''

Raymond Patriarca was brought before the committee from the Atlanta Federal Penitentiary, where he was serving 10 years for murder conspiracy. Asked if he knew Sinatra, the boss of New England organized crime said:

A: I never met Sinatra personally. I seen him on television and at the moving pictures.

Q: Did you ever have any business dealings with him?

A: No, sir.

Q: Did you ever purchase stock from him?

A: No, sir.

Q: Anybody on your behalf do it?

A: I claim my Fifth Amendment privilege.

Q: Do you have any knowledge that anyone associated with you had any business dealings with Sinatra?

A: I claim my Fifth Amendment privilege.

It may be true that Sinatra never met Patriarca personally, but Mickey Rudin, Sinatra's attorney, had earlier acknowledged his client's friendship with Gaetano Lucchese, and Patriarca's testimony left the question of his role in Berkshire Downs in question.

The committee members, apparently intimidated by Sinatra, virtually apologized to him before they were through. Representative Charles Rangel, of New York, who was a beneficiary of Sinatra's fundraising, told him, ''You're still Chairman of the Board.''

Sinatra kept up his attack on the committee after his 95-minute appearance. Shortly afterward he sent the committee a bill for $18,750 in expenses. It was never paid, but in July The New York Times published a commentary bearing Sinatra's byline wherein Sinatra claimed that the committee had invaded his privacy in order to gain publicity during an election year. The committee backed down and no further action in the Berkshire Downs case was taken.

President Nixon, happy over the embarrassment of the congressional committee, made a personal phone call of congratulations to Sinatra. This personal contact from the President, and Sinatra's friendship with Vice-President Agnew, led to Sinatra's support of Nixon's re-election in 1972.

Sinatra's changing political parties helped him strengthen his political influence in the next two decades. It also led to his most blatant illegal actions in support of his organized-crime friends.

The Pardon of Angelo ''Gyp'' DeCarlo

Angelo ''Gyp'' DeCarlo was a caporegime, or captain, of New York's Genovese family. DeCarlo was called ''a methodical gangland executioner'' in FBI files. This assessment was upheld by the 1970 release of transcripts of the electronic surveillance of Sam ''The Plumber'' Decavalcante and by the testimony of mob defector Gerald Zelmanowitz.

In September 1968, according to Zelmanowitz' testimony, Zelmanowitz had visited DeCarlo's office only to find Louis Saperstein ''lying on the floor, purple, bloody, tongue hanging out, spit all over him.'' Saperstein owed $400,000 to the Genovese family and was having problems paying the $5000 per week interest.

According to Zelmanowitz' testimony, ''I thought he [Saperstein] was dead. He was being kicked by Mr. Polverino and Mr. Cecere. He was lifted up off the floor, placed in a chair, hit again, knocked off the chair, picked up and hit again.'' DeCarlo ordered his men to stop the beating and told Saperstein to repay the loan by December 13 or he would ''be dead.''

Saperstein died on November 26, 1968, of what was called ''gastric upset.'' Before his death he had written to the FBI telling them of the threats that had been made by DeCarlo. This letter prompted an autopsy that found a large amount of arsenic in Saperstein's body.

In March 1970, DeCarlo was convicted of conspiracy to commit murder, based partly on the testimony of Zelmanowitz, and sentenced to 12 years in a federal penitentiary. According to the FBI file, in 1972 while DeCarlo was incarcerated in Atlanta, Frankie Valli and ''The Four Seasons'' performed for the prisoners. DeCarlo asked Valli to get in touch with his [DeCarlo's] old friend, Frank Sinatra, and ask him for help.

By this time Sinatra was very close to both President Nixon and Vice-President Agnew. Nixon, of course, was in need of money for his re-election campaign. According to the FBI files, Sinatra made a $100,000 cash contribution to Maurice Stans. Peter Malatesta, a member of Agnew's staff and a close friend of Sinatra, contacted John Dean and asked for a presidential pardon for DeCarlo.

Sinatra made another payment of $50,000 in December 1972, and two days later DeCarlo was pardoned. The grounds for the pardon were that DeCarlo was terminally ill, but according to Newsweek and the FBI file, DeCarlo was soon ''back at his old rackets, boasting that his connections with Sinatra freed him.'' He died the following year of cancer.

The FBI dismissed the allegations against Sinatra, but Senator Henry Jackson of Washington, chair of the Senate Permanent Committee on Investigations, charged that the pardon ''bypassed normal procedures and safeguards.'' Jackson's investigation led to serious charges against President Nixon, the U.S. Marshall Service and the IRS, but action was pre-empted by Agnew's resignation and the Watergate scandal. No charges were ever brought against Sinatra.

In the late 1960s Sinatra took on the role of an organized-crime icon. The top hoodlums of whatever city he appeared in heavily attended his concerts. Among the people who attended his performances regularly were Santos Traficante Jr., boss of Florida, Carlos Marcello, boss of New Orleans, Frank Piccolo, Gambino family capo in Connecticut, Frank Balistieri, boss of Milwaukee, as well as a host of lesser mobsters.

In 1964, Sinatra's connections to the mob were so well known to the FBI that Special Agent Elison, of the Las Vegas division, attempted to develop Sinatra as an informant. Elison and Sinatra had become friendly during the investigation into the kidnapping of Frank Sinatra Jr. FBI director J. Edgar Hoover and Clyde Tolson discouraged this plan and it was dropped.

Sinatra was often used by the mob for his fame and his connections in politics and entertainment. Sometimes he was the victim of their schemes and by the late '60s skimming the proceeds from Sinatra performances was a favorite activity of mobsters. Sinatra, for his part, gained prestige and self-esteem from his association with mobsters. He also gained a great deal of wealth. He died May 15, 1998 in Los Angeles of heart attack at age 82. He wasn't a ''made'' Mafioso, but the Mafia made him.

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