CHAPTER EIGHT

Lucky Luciano wants total control.

More than twenty of the most powerful men in organized crime have been summoned to this island paradise. It is ten months since Luciano was released from prison in New York. He has established a presence in Italy and is now moving to consolidate his underworld power. Each gangster present has already given Luciano a thick envelope filled with cash to show respect. It is money Luciano will use to buy an ownership stake in the Hotel Nacional, the stately waterfront casino and hotel in which the gangsters now gather. His ownership in the hotel will allow him to make a new home in Cuba.

This weeklong “Havana Conference” is the first meeting of America’s top crime bosses since 1932. A single well-placed explosive device could radically alter the leadership of organized crime, so security is tight. Armed guards prowl the hallway outside the conference room doors. The Hotel Nacional was built for tourists, not locals, and the people of Cuba are forbidden from even entering its grounds. But during the conference those restrictions are even more stringent. The entire mezzanine floor is off-limits to other hotel guests, allowing the bosses to meet, drink rum, and dine without threat of interruption. In addition, the top four floors of this six-story establishment are allocated for the gangsters and their subordinates.

The Havana Conference is top secret, and decades later the actual number of attendees will still be open to debate. But it is known for certain that Mafia leaders from New York, Chicago, New Orleans, and Tampa are in attendance. Wives and girlfriends are not allowed to arrive until Christmas Eve.

Officially, the gangsters have all come to see the young Italian crooner from New Jersey, Frank Sinatra, perform downstairs in the showroom. Lucky Luciano himself has personally funded Sinatra’s rise to celebrity. The young singer’s ancestors lived in the same Sicilian town in which Luciano was born, and Lucky is eager to meet the thin, thirty-one-year-old singer for the first time.1


The powerful Luciano sits at the head of a highly polished wooden conference table. Despite the tropical setting, he wears a dark suit and tie. Luciano is hardly an anonymous figure in Havana but now goes by his given name of Salvatore in order to help maintain a low profile. Each man at this meeting has specific orders not to call him Charles or Lucky. Luciano is now forty-nine but remains trim and powerful, with a full head of black wavy hair.

Ideally, the Havana Conference would have taken place in New York, but Luciano is forbidden from entering the United States. The gangster believes that stipulation is temporary, and it will be just a matter of time before he can arrange a bribe with New York governor Thomas Dewey to make possible his return. Luciano knows that the ambitious Dewey is planning to run again for president, having been beaten by Franklin Roosevelt in 1944. A hefty contribution to the governor’s campaign fund should be enough to get him back into America.

Until then, Luciano must be patient, conducting his business in places like Cuba without interference from the FBI or Internal Revenue Service.

The Mafia is always welcome on this island nation. And where the Mafia is welcome, it soon finds a way to make money. Sugar is Cuba’s main product, but Havana is also home to hundreds of brothels, making the sex trade a source of Mob income. Cubans are also so fond of narcotics that one local writer has noted that “as a consumer nation of hard drugs, Cuba occupies first place.” So far, the Mafia has not entered the business of drug trafficking, but it is just a matter of time before it does so.

The gangsters know that the Cuban people do not have much money. Their real source of income comes from Americans. U.S. citizens view Cuba as an island of “prostitutes, cigars, abortions, resort life, and pornographic movies,” in the words of one journalist.

Prominent American playwright Arthur Miller describes Cuba as “hopelessly corrupt, a Mafia playground, a bordello for Americans and other foreigners.”

Americans flocked to Cuba during Prohibition, eager to enjoy the mojito and Cuba libre—rum cocktails specially created for U.S. tourists by Havana bartenders. But Prohibition ended more than a decade ago, and the Mafia knows that prostitution and drugs are not enough to consistently lure Americans back.

The future is resort casino gambling. Done properly, gambling is lucrative, consistent, and more glamorous than the sordid pursuits of prostitution and drugs. And unlike in America, gambling is legal in Cuba.

The Cuban government would certainly welcome a steady stream of Americans, bringing with them the money and the loose morals that lubricate the island’s tourist economy.

Cuba is currently run by President Ramón Grau San Martin, who entered office in 1944. His predecessor, Fulgencio Batista, considered by many to be a gangster himself, looted the national treasury just before stepping down. This puts the San Martin regime in the unlikely position of needing unconventional sources of revenue to fund the economy. The Mafia is happy to oblige with hefty bribes and a piece of the action.

At the time of his election, President San Martin was viewed as an idealistic savior “chosen to effect the moral liberation of our youth.” But his two years in office has shown the president to be only slightly less corrupt than the ruthless Batista. The Cuban president well knows that allowing gangsters to meet so freely in Havana could one day lead to a lucrative partnership between the island nation and the Mafia.2


As the gangsters settle into their seats around the long table, Lucky Luciano smokes a cigarette.

Seated just six feet away from him is the one man standing in the way of Luciano being named Capo Di Tutti I Capi—Boss of All Bosses. Vito Genovese is a longtime rival whom Luciano often refers to as the “fat pig.”

Genovese, a brutal psychotic, is notorious for favoring violence over diplomacy. Once, after falling in love with a woman already married to another man, he solved the problem by strangling the husband on a Manhattan rooftop. The widow married Genovese twelve days later.

Though born just three days before Luciano, Vito Genovese has the strained face and receding hairline of a much older man. He is shorter by three inches, with a broad waistline and thick black eyebrows. His suit is wrinkled and coated with a fine layer of ash from the cigar he now smokes.

What Vito Genovese lacks in physical presence, however, he more than compensates for with conniving and guile. He has been through the same New York Mob wars as Luciano, whom he once considered a friend. In fact, the recent history of the New York Mafia can be traced through the actions of both men.

In this handout photo provided by the New York City Police Department, reputed mobster Vito Genovese is shown in a police mugshot in New York City, July 1946.

In 1931, Genovese and Luciano took part in the legendary murder of “Joe the Boss” Masseria at an Italian restaurant in Brooklyn. At the time, Luciano served as Masseria’s top lieutenant but it was Genovese who engineered the complex hit that ensured he would personally take over Masseria’s crime family.

Normally surrounded by four bodyguards, the burly Masseria was mysteriously left alone at the table in Nuova Villa Tammaro, even as Lucky Luciano excused himself to use the restroom. Suddenly, a hit team consisting of Genovese, Bugsy Siegel, and Joe Adonis burst into the restaurant and gunned down Masseria, shooting him four times in the back and once in the head.

The assassination brought Luciano and Genovese to leadership roles in the New York underworld, but their friendship ended when Lucky was sent to prison in 1936. In Luciano’s absence, Vito Genovese became acting boss of the Luciano family. But Genovese saw the role as a lifetime position rather than a temporary one. Lucky Luciano never forgave him. In 1937, Genovese was forced to flee to Italy to escape murder charges, whereupon Luciano appointed his protégé Frank Costello to run the family until his release.

Vito Genovese prospered in exile, successfully creating black market operations during World War II. The totally amoral Genovese actually pilfered money and goods from British and American forces and then funneled them into Nazi Germany. After the Allies took control of the Italian mainland, Genovese was appointed a liaison officer at the U.S. Army headquarters in Naples. The move so emboldened Genovese that he returned to America once the war ended to face the 1937 murder charges.

Things worked out well for Vito. The two leading witnesses were found murdered before they could testify. The case was dismissed.


Yesterday, for the first time in ten years, Luciano and Genovese met face-to-face in Lucky’s villa a couple of blocks from the Hotel Nacional.

“You been away a long time,” Genovese says after lunch. “You don’t realize how much things are changing.”

“You’ve been away a long time, too, Vito. What are you getting at?”

“I think you ought to quit—I mean, retire,” Genovese proposes. He has come to Havana to retake control, confident in the secret knowledge that his rival will never be allowed to return to the United States—and that all power, eventually, will be his and his alone.

Luciano fumes. “Right now you work for me and I ain’t in no mood to retire. Don’t you ever let me hear this again, or I’ll lose my temper.”

Genovese knows better than to force the issue. He remains silent. Moments later he asks for a lift back to the hotel.

“I had a car with a driver and I sent him back,” Luciano will recall. “Naturally, I realized that he went away unhappy, but I didn’t give a fuck. I knew there were enough guys on my side to keep him in line. So all that fat little bastard could do was dream.

“I’ll tell you one thing, though: it wasn’t easy to keep my hands off his fat throat. He’ll never know how close he came to it.”


Lucky Luciano opens the Havana Conference with a few jokes and words of greeting. He alludes to the fact that there has not been a Boss of All Bosses in the American Mafia for more than fifteen years. The job was once his for the taking, he reminds those in attendance, but in the name of a more united Mafia family he has long chosen not to accept the title.

Times have changed. With the war now over, and the days of Prohibition and bootlegging long gone, the Cosa Nostra (“our thing”)—as the alliance of Mafia families is also known—needs a single leader to guide its business.

The members listen quietly, allowing Luciano his say. The selection of a Boss of All Bosses and the decision about whether or not to become more active in the narcotics trade are two of the most important topics of these meetings.

To Lucky Luciano’s right sits his top lieutenant, the dapper Frank Costello. He has run the Luciano crime family during Lucky’s time in prison but has no intention of making that a permanent arrangement. Costello has been part of organized crime his entire life, working not just with Italian families but also Jewish and Irish mobs. In addition to being handy with a gun, he has also worked closely with organized crime syndicates in New York, New Orleans, and Los Angeles on a number of illegal ventures focused around gambling, such as slot machines and horse racing. Costello’s decade as head of the Luciano crime family during Lucky’s imprisonment was a time of prosperity, and he was a popular leader. But Costello is not reluctant in the slightest to hand the reins of the family back to his boss. The Italian-born Francesco Costello is utterly loyal to Lucky Luciano. He is more than content to bear the trusted title of consigliere—that of counselor and adviser.


To Luciano’s left sits Meyer Lansky, the forty-four-year-old Russian-born Jewish mobster who also showed loyalty to Luciano throughout his many years in prison. It was Lansky who arranged the Havana Conference and who dictates the business agenda.

Based in Miami, and known as “the little man” and “the Mob’s accountant,” the five-foot-tall Lansky is the brains behind the National Crime Syndicate’s cash flow. His specialty is managing the gambling operations, both legal and illegal, which have become such a huge source of revenue.

Meyer Lansky (1902–83), American gangster, on the steps of the Federal Courthouse in Miami, Florida, February 28, 1973.

Lansky has a particular fascination with Cuba. He not only enjoys the island’s lifestyle and climate but is intent on bringing a different sort of casino gaming to the island. Currently, gambling in Cuba often relies on sleight of hand by the dealer. Lansky knows that casual tourists might put their money down for such trickery, but big money gamblers who put thousands of dollars on a single bet will stay away. The players are looking for an honest game. Once Mafia casinos are built, the mobster envisions a school here in Havana to train card dealers to be straight.

Benjamin “Bugsy” Siegel poses after apprehension in Los Angeles on April 17, 1941, in connection with an indictment returned in New York charging him with harboring Louis “Lepke” Buchalter.

Unlike the Italian bosses seated around the table, Lansky and the Jewish representative from New Orleans, “Dandy Phil” Kastel, will not be allowed to vote on any issues presented this week because they are not members of the Unione Siciliana. But out of respect, they are allowed to speak their mind.

Lansky, in particular, has something very urgent that needs to be discussed. The problem is his trusted childhood friend and fellow associate Jewish mobster, Benjamin “Bugsy” Siegel.

Meyer Lansky has long supported Siegel’s attempt to turn a dusty truck stop in southern Nevada into a destination resort focused around casinos. Nevada formally legalized gambling in 1931 as a budgetary remedy against the financial hardships of the Great Depression. Other states have forms of legalized betting such as horse races and even bingo, but Nevada’s decision to allow statewide gaming makes it the only state to mimic Cuba in its embrace of casinos.

Thus far, Nevada has not seen enormous returns on this law due to its remote desert location. But the growth of air travel means potential gamblers no longer have to drive for days to roll the dice. That has caught the attention of Meyer Lansky.

“Las Vegas,” as Bugsy Siegel’s proposed gambling mecca is now known, is close to Los Angeles and is accessible to the glamorous Hollywood crowd.

Using money borrowed from the Mafia, Siegel is building a new resort-casino known as the Flamingo. There, guests will be treated to the very best in entertainment and luxury at rock-bottom prices, knowing that gambling revenue will drive the profit margin.

But Siegel has managed the construction poorly and the Mob’s patience is being tested. Cost overruns have been enormous, inflating the original price from just over $1 million to almost $6 million. Siegel has gone outside the Mafia to seek loans, effectively taking his business into the public realm.

There are also disturbing rumors that Siegel is skimming money for his own enrichment. Siegel’s mistress, Virginia Hill, has been seen flying to Switzerland to deposit enormous sums in bank accounts. She also recently leased a Swiss apartment, leading some to speculate that Hill and Siegel are scheming to flee America.

“There was one thing everybody was sure of,” Lucky Luciano will later recall. “On them nights that Bugsy spent on the pillow with her, he spilled enough into her pink ear about the outfit and the top guys that could cause plenty of trouble. The logical thing was to get rid of her.”

The same holds true for Bugsy Siegel.

Though most rooms at the Flamingo are unfinished, the casino is due to open in just six days. The Mafia is growing impatient for a return on its investment, and though the day after Christmas is considered the worst possible time to open a new hotel or restaurant, Bugsy Siegel is eager to prove his brainchild a success. A late-night phone call from Las Vegas to Cuba after the opening will inform the conference about his progress.

Mink-bedecked Virginia Hill Hauser, onetime girlfriend of slain mobster Bugsy Siegel, listens to a question from the Senate crime probers in New York, March 15, 1951, and provides an answer with an expressive wave of her hand.

If the Flamingo is successful, every man in this room will cheer.

If it is not, Bugsy Siegel will be killed.


Next to Meyer Lansky sits Giuseppe Antonio Doto, a.k.a. Joey Adonis. The seating choice is a display of power, reminding all in the room that Adonis is yet another intensely loyal follower of Lucky Luciano. In their teenage years, Luciano, Bugsy Siegel, Meyer Lansky, and Adonis ran their own bootlegging operation in Brooklyn. Like Luciano and Al Capone, Adonis once worked for mobster Frankie Yale. After Yale was assassinated in 1928, it was Adonis who took over the dead man’s operation.

Former casino operator Santo Trafficante Jr. (left) of Tampa, Florida, was detained by police in Havana, Cuba, June 10, 1959. He is in the custody of police captains Sergio Martin Vidal (center) and Ignacio Barbon (right).

Vain and fixated by mirrors, Adonis was once offered the chance to murder Lucky Luciano by a rival gang. Instead, he warned his boss about the hit. That display of loyalty has never been forgotten.


The list of high-level mobsters continues down the length of the meeting room table: Joe Bonanno and Tommy Lucchese of New York; the up-and-coming thirty-seven-year-old Sam Giancana from Chicago; Carlos Marcello from New Orleans; Santo Trafficante from Tampa; and many others.

But all eyes are on Lucky Luciano and Vito Genovese, who is seated next to Joey Adonis.

“Charlie, pardon me if I interrupt,” says hit man and alleged saboteur of the SS Normandie, Albert Anastasia, as Luciano is about to conclude his opening remarks. The trigger-happy mobster sits directly across from Vito Genovese—a man who wants him dead. Genovese has quietly been sounding out other Mob leaders about a hit on Anastasia.

But “Mad Albert” is unafraid and now takes it upon himself to crown Luciano as the Boss of All Bosses.

“I want to say this in front, before the meeting goes any further. For me, you are the big boss, whether you like it or not. That’s the way I look at it, and I would like to hear from anybody who don’t feel the same way.”

Anastasia glares at Genovese, daring him to make a claim to the top spot. Silence fills the room.

Luciano speaks up. “When I was in Italy, I heard about the trouble between Vito and Albert. I also heard some news about other guys who was trying to move in.”

The gangster then continues to speak for another hour, reminding everyone that their greatest enemy is jealousy. “In our kind of business there’s so much money to be made that nobody has the right to be jealous of anybody else.”

As planned, Luciano veers away from the rivalry, instead focusing on the Mafia’s future under his control. Many in this room are in favor of adding narcotics trafficking as a revenue source. Foremost among them is Vito Genovese, who has argued vigorously for a Mafia business expansion into drugs. Heroin, for instance, is much easier to transport and has a much higher profit margin than the alcohol the Mafia once smuggled during Prohibition. Another advantage to hard drugs is that they can be used to enslave and blackmail people.

But Luciano is adamantly opposed to the narcotics traffic. “It had become clear to me that there was so much dough to be made in everythin’ else we had, why ruin it with the dangers of playin’ around with junk that would only bring the federal guys down on us?” he asked.

“People wanted to gamble, we helped ’em gamble; they needed booze, cigarettes and meat durin’ the war, we took care of that. Sure, here and there we would squeeze some guys, but on the other hand, look at all the money we was puttin’ in circulation just from other good businessmen buyin’ our protection.… There wasn’t a politician or a cop who could hold on to none of the money we paid him off with … they spent it as soon as they got it, and that was very good for the American economy.”

Luciano looks to his left, directly into the eyes of Meyer Lansky.

Both men burst out laughing, followed by everyone else in the room. But as the tension deflates, Lucky Luciano knows that he has lost the argument against drugs—and all because Vito Genovese quietly went from delegate to delegate before the meeting, lining up votes in favor of narcotics trafficking.

Advantage Genovese.

Luciano knows better than to go against the majority and quietly accepts the loss.

Ironically, he well knows that his name will become associated with narcotics once the Mafia begins selling “junk.” As Boss of All Bosses, federal authorities will treat Luciano as the instigator of the drug trade.

Thus, Luciano’s attempt to return to America will be made even more difficult. Vito Genovese has engineered the whole drug thing to defeat the Boss of All Bosses.

Knowing he has been defeated, Luciano sits back down. Frank Costello leans over. “Charlie, don’t hit your head against the wall. Vito rigged it before the meet started.”

“Frank was right,” Luciano will later remember. “Vito won that round.”

But Vito Genovese is not finished.


The time is 4:00 a.m. Lucky Luciano is going to bed after a long evening. The Flamingo has finally opened in Las Vegas on a cold and rainy night. Despite the presence of heavyweight entertainers Jimmy Durante, Xavier Cugat, and George Jessel, few guests made the journey across the desert from Hollywood for the grand opening. Bugsy Siegel only made matters worse, verbally threatening customers and even evicting one group.

Siegel’s fate is all but sealed.

Meyer Lansky, in a desperate attempt to recoup the monies lost by the Mafia and hoping to save the life of his good friend Bugsy, has persuaded Luciano and the other delegates to allow him a bit more time to come up with a last-ditch plan for saving the Flamingo. But the assassination clock is ticking.


As the Mob meeting in Havana comes to a close, Lucky Luciano is depressed. An old friend might soon be killed and his organization might be out millions of dollars in Las Vegas. Luciano begins walking slowly from the gathering.

But Vito Genovese intercepts him, asking if they might talk. He invites Luciano to his penthouse suite. The two men ride the elevator in silence. Immediately upon entering his room, Genovese bluntly informs Luciano: “I want half of Italy.”

“What are you talking about?”

“I set up the whole thing in Europe,” Genovese tells Luciano. “The black market. The truck routes to Germany, everything. It’s waiting for you when you get back.”

“You’re nuts, Vito. I ain’t going back. I’m staying in Cuba.”

“I understand different,” Genovese responds. “I heard that Washington knows you’re in Havana and they’re putting the screws on those jerks in Cuba to get you thrown out. There’s gonna be so much heat that nobody can do nothing to help you. Charlie, you’re gonna have to get out of here and go back to Italy. By rights, everything over there is half mine—and I want it.”

Luciano’s worst fears are confirmed. He is all but certain that Genovese has tipped off the U.S. government about his stay in Havana. “The dirty cock was trying to take me,” Luciano will remember. “Vito figured he could muscle me out and finally get the last step up the ladder and be the Boss of Bosses.”

Luciano has a personal code of nonviolence toward other members of the family. Such an honor violation could lead to a hit being called on him. But Lucky Luciano can’t help himself. He now breaks his own rules.

“I done something I’ve never done before,” Luciano will recall. “I pushed him up against the wall and beat the living daylights out of him.

“He was a tough little prick, but I was bigger and a helluva lot tougher. Besides, I was damn mad. I started to knock him around the room like he was a rubber ball. I didn’t hit him in the face—I didn’t want to mark him up. I just belted him in the guts and the kidneys, and when he fell down I just started to kick him in the belly, and every shot I took with my fists and foot I told him he was only a shit and a son of a bitch and a dirty rotten Neapolitan louse—even worse, he was a fink American who turned on his own country like a fucking traitor.

“I beat him up so bad he couldn’t get out of his room for three days.”

Vito Genovese is diagnosed with three broken ribs and a fractured left arm. Under penalty of death, the hotel doctor is ordered by Luciano to say that Genovese slipped in the shower.

The Havana Conference has come to an end.

But things have not ended for Genovese and Luciano.


The date is February 23, 1947. Lucky Luciano is enjoying Saturday lunch in the Vedado section of Havana, just around the corner from the Hotel Nacional. Tipped off by Genovese, the American government is angered by Lucky’s presence in Havana. Syndicated columnist Walter Winchell has published the mobster’s whereabouts in the swank Havana suburb of Miramar, leading to magazines like Time and Newsweek publishing their own stories about the famous gangster.

Soon, the United States demands that Luciano be deported from Cuba. However, the Cuban government ignores the command. Benito Herrera, head of Cuba’s Secret Police, argues in favor of the island’s sovereignty and refuses to arrest Luciano. Alfredo Pequeño, the Cuban minister of the Interior, has even formally reminded the American embassy in Havana that Luciano is not currently doing anything illegal.

But Lucky is nervous, unable to forget his recent confrontation with Vito Genovese. “I couldn’t shake the feelin’ I had about Vito blowin’ the whistle on me in Washington,” he will later recall.

Lucky Luciano’s feeling is correct.


It has been two months since the Havana Convention. Since its decision to enter the world of narcotics, the Mafia has moved quickly to import more heroin and other hard drugs into the United States.

The director of the Federal Bureau of Narcotics, Harry Anslinger, believes Luciano’s presence in Havana is the reason for the drug flow. The fifty-four-year-old law enforcement official has held his job since 1930 and has waged a ferocious war on alcohol and cannabis—both seen as societal evils. Now he turns his focus to heroin.

But Anslinger does not pursue suspects on an equal basis. He is openly racist, believing that drugs wrongfully encourage relations between blacks and whites. Even worse, it encourages racial parity. “Reefer makes darkies think they’re as good as white men,” he has written.

Anslinger also believes jazz musicians “reek of filth” and has arrested prominent stars like Louis Armstrong and Billie Holiday for alleged drug use, knowing the busts increase the prominence of his bureau, which competes with J. Edgar Hoover and the FBI for prestige. Like Hoover, the heavyset Anslinger has enjoyed close relationships with several presidents, allowing him to pursue a highly personal law enforcement agenda.3

Director Anslinger’s disdain for jazz musicians and minorities is closely matched by his hatred for Italians and the Mafia—in particular for Lucky Luciano.

“Lucky,” Anslinger will tell True magazine, “is the largest single figure in the traffic of this (drug) contraband in America today.”

In fact, Harry Anslinger is obsessed with Lucky Luciano, seeing the mobster as the most high-profile suspect in his bureau’s history. Anslinger is so consumed by Luciano that he will soon write a book about “The Boss,” as he titles the unpublished work.4

So despite Cuba’s protection of the mobster, Anslinger refuses to back down. He meets personally with President Harry Truman, stating that the flow of drugs from Havana to the United States has profoundly increased in the last two months because of Lucky Luciano.

Truman gives Anslinger the approval to do whatever necessary to remove Lucky Luciano from Cuba. The response is an embargo of all medicines from America. This means that patients in Havana hospitals will suffer and die.

The Cuban government postures, announcing publicly that Lucky Luciano has nothing to do with the illicit flow of drugs into America. But the corrupt politicians can only hold out for so long.

Finally, Cuba buckles to Anslinger and Truman. Cuban secret police arrest the gangster for drug trafficking. He is deported back to Italy, where he is thrown in prison upon landing in Genoa. Eventually he is released, but Lucky Luciano will never again be a force in organized crime.5

Yet Vito Genovese is still not the boss. It is Frank Costello who once again takes control of the Luciano crime family.

But being a Mafioso is a lifetime commitment. So Genovese is content to bide his time, awaiting the moment to strike. And when that moment comes, it will be vicious.