CHAPTER 4:
TRIUMPH OF THE CUBAN REVOLUTION
On December 31, 1958, General Fulgencio Batista, his family, and inner circle gathered to celebrate the arrival of the New Year at the Cuban army headquarters at Camp Columbia on the outskirts of Havana. Instead of toasting the New Year at midnight, however, Batista informed his guests that the military situation in Cuba was hopeless. He had been advised that Santa Clara and Santiago de Cuba would fall soon to the July 26th Movement. He told the celebrants to report to the Camp Columbia airfield in two hours, ready to go into exile.
Historian Thomas Paterson writes, “They fled so fast that they left sheaves of documents behind—evidence of corruption and crimes that the victorious rebels would soon use to demonstrate why the insurrection had been necessary.”
Batista had already moved the bulk of his fortune, estimated at $300 to $400 million, out of Cuba. His money was deposited in secret bank accounts and invested in real estate in Florida, New York, Switzerland, and elsewhere. But in his haste to flee Cuba, he left behind $11 million in stock certificates.
In the wee hours of January 1, 1959, the pilots of three Cuban air force DC-4s at Camp Columbia fired up their engines, roared down the runway, and lifted their U.S.-supplied aircraft into the darkness of the night. Batista wanted to return to his old home in Daytona Beach, Florida, but President Dwight D. Eisenhower would not allow him to land in the United States. Instead, Batista flew to the Dominican Republic.
When Habaneros turned on their radios on New Year’s Day and heard the song “Mama, They’re from the Hills,” they knew something big had happened overnight. Batista had banned the song from Cuban airwaves because of its association with the July 26th Movement guerrillas in the Sierra Maestra. As the news spread that Batista had fled the island, people filled the streets and celebrated.
A few hours later, angry Habaneros gathered outside Mafia establishments. Men with sledgehammers smashed the plate-glass windows of the Sevilla-Biltmore Hotel; others swarmed into the hotel and tore up the lobby and casino. The damage was estimated at $250,000. A few blocks away, a crowd broke into the casino at the Plaza Hotel. Gaming tables, roulette wheels, and slot machines were dragged into the street and set on fire.
Menacing throngs were turned away from the Hotel Nacional and the Hotel Capri, although not before they inflicted considerable damage on the Capri’s lobby. Seven of the thirteen casinos in Havana suffered major damage, including the gaming rooms of the Deauville, Plaza, and Sevilla-Biltmore hotels. Slot machines were stolen from the Sans Souci.
The July 26th Movement set up their headquarters in the Havana Hilton, a luxurious symbol of gangsterismo, and renamed it Hotel Habana Libre. As the long-haired July 26th Movement guerrillas, known as barbudos (men with beards), arrived in Havana, they took up residence in the hotel built with funds from the hotel- and restaurant-workers union controlled by Batista.130 Cubans also vented their pent-up anger on curbside parking meters, a galling reminder of Batistiano corruption. The Times of Havana reported, “Young boys with sticks smashed parking meters and threw them into the streets.” When the Bastistianos installed the parking meters, they had said the revenues would be used to support soup kitchens and other charitable projects. Instead, the money from the meters went into the pockets of Batista’s brother-in-law General Roberto Fernández Miranda.131
There was also looting in suburban Miramar. The houses of Brigadier General Pilar García, Batista’s relatives, and senior government officials were burglarized. García, chief of the National Police, was infamous for his ruthless use of the police to break up demonstrations and intimidate opponents of the Batista regime.
From Oriente province, Fidel Castro called for calm in Havana. Public order was restored in the capital as Habaneros awaited the arrival of Castro and his triumphant July 26th Movement guerrillas.132
In Santiago de Cuba, Fidel Castro tapped into Cuban nationalist sentiments in his first remarks about the Cuban revolution. He compared it to the Cuban War of Independence, the long anticolonial insurrection against Spain that started in 1868. “This time the revolution will not be thwarted,” Castro declared on January 2, 1959. “This time fortunately for Cuba, the revolution will be consummated. It will not be like the war of 1895, when the Americans arrived and made themselves the masters of the country; they intervened at the last minute and later did not allow [Cuban General] Calixto García, who had been fighting for thirty years, to enter Santiago de Cuba.”
Castro continued, “It will not be like 1933, when Machado was ousted and the people began to believe that a revolution was taking place, but then Batista took over the reins and instituted a dictatorship lasting eleven years. It will not be like 1944, when the multitudes were fixed with the idea that at last the people had come to power, but those who had really come to power were thieves. Neither thieves nor traitors, nor meddlers, this time it will really be the revolution.”
In subsequent speeches, Castro returned to the dream of Cuba libre of Cuban patriot José Martí, who had been killed leading the last phase of the Cuban war of independence in 1895. On February 23, Castro declared, “The mambises (the 19th century Cuban guerrilla fighters) initiated the war for independence we completed.” His references to the dashed hopes of 1898 struck a responsive chord after the defeat of Batista as Cuban national pride swelled.133
Castro and his guerrillas set out from Santiago de Cuba on a five-day journey to Havana in a motley caravan of civilian and military vehicles. The guerrilla fighters were welcomed as heroes by cheering crowds along the 600-mile route. Images of Castro, a bearded warrior with a rifle slung across his shoulder and a cigar in his hand, were broadcast on live television from one end of the island to the other.134
In Havana, Castro spoke briefly at the Palacio Presidencial and later at Camp Columbia. Castro praised the rebel army and stressed the need for unity. He called on all anti-Batista rebels to lay down their arms. A white dove, one of several palomas set free in an opening ceremony, landed on Castro’s shoulder as he spoke. The crowd chanted wildly, “¡Fidel! ¡Fidel! ¡Fidel!”
But the Directorio Revolucionario, which occupied the Palacio Presidencial and the Universidad de la Habana, refused to lay down its arms. DR Comandantes Faure Chomón Mediavilla and Rolando Cubela Secades insisted that their July 26th Movement rivals share power with them. As we have seen, Carlos Prío and the Mafia gamblers provided arms to the DR and the SFNE to create a counterweight to the July 26th Movement.
The Directorio Revolucionario reluctantly agreed to disarm, and Chomón and Cubela accepted mid-level posts in the revolutionary government. But Cubela, in particular, remained at odds with the Castro-led revolution.
He was appointed military attaché at the Cuban Embassy in Spain in March 1959. Before his departure for Madrid, Cubela had a meeting with Castro in which he expressed strong dissatisfaction with the course of the Cuban revolution. At the same time, according to an FBI memorandum, “Cubela… privately told intimates that he was so disgusted with Castro that if he, Cubela, did not get out of the country soon, he, himself, would kill Castro.”
Nonetheless, the balance of power in Cuba had shifted decisively to Castro and the July 26th Movement in January 1959. With the swearing-in of Manuel Urrutia Lleó as provisional president of Cuba on January 3, the July 26th Movement signaled its intention to reach beyond its ranks in forming a revolutionary government. Urrutia had been a judge in Oriente province who had acquitted July 26th members in a 1957 case, ruling it was not a crime to rebel against the Batista dictatorship.
Paterson writes, “The naming of Judge Urrutia’s cabinet reassured observers who had warned against Castro’s radicalism.” He notes, “Many of the appointees were professionals, moderates from the middle class.” The Cabinet also included José Miró Cardona, dean of the Faculty of Law at the University of Havana, Rufo López-Fresquet, finance minister under President Carlos Prío Socarrás, and the respected economist Felipe Pazos. Castro did not attend Cabinet meetings, but he was the preeminent leader of the revolution as comandante en jefe (commander-in-chief) of the Cuban rebel army.135 But Washington was slow to respond to the rapid developments in Cuba.
President Dwight Eisenhower had not paid close attention to the situation in Cuba in 1958. The minutes of an October 30, 1958 meeting of the National Security Council (NSC) stated, “The President inquired why Batista had apparently never really made a genuine effort to quash this rebellion.” The memorandum noted, “[Director of Central Intelligence] Allen Dulles replied that Batista had tried, but simply had been unable to achieve success.”
Eisenhower searched for a means by which to prevent Castro from coming to power. He approved former U.S. diplomat William D. Pawley’s plan to persuade Batista to resign. Pawley, owner of the Havana Trolley Co. and Havana’s bus system, had been U.S. ambassador to Brazil and Peru, and knew Batista personally.
Pawley met with Batista at the Palacio Presidencial for three hours on December 9, 1958. According to Pawley, he proposed a quid pro quo designed to isolate Castro: Batista would hand over power to a “caretaker government,” which would receive U.S. support; Batista could return to his residence-in-exile in Daytona Beach. But Batista turned him down. Nine days later, Allen Dulles informed the NSC that the end was near for Batista. A memorandum on the NSC meeting stated, “The Intelligence Community believed that Batista would be unable to muster enough strength to save himself and that Castro would probably emerge the victor in what had now become a civil war.”
Atomic Energy Commission Chairman John McCone told the NSC that Castro and the July 26th Movement enjoyed enormous popularity in Cuba. The memorandum stated, “McCone reported that during his recent trip to Cuba he was told that 95% of the people supported Castro.” At a December 23 NSC meeting, Eisenhower expressed hope that a “third force” could be organized to counterbalance the July 26th Movement. A memorandum on the NSC meeting stated, “The President saw hope of a ‘third force’ growing in strength and influence if it were organized around an able man and provided with money and arms.” To his chagrin, Eisenhower learned that there was little the United States could do to stop Castro and the July 26th Movement.
Instead, the Eisenhower Administration pondered why Batista was “hated.” Assistant Secretary of State for Inter-American Affairs Roy Rubottom found two reasons; “First, because he took [the] constitutional process away from the people, and second, because of recent repression and some brutal treatment of the people.” Chief of Naval Operations Arleigh Burke focused on Batista’s corruption: “Admiral Burke felt that Batista’s private interests had gotten in the way of his public interests.”136
In a memorandum, Under Secretary of State C. Douglas Dillon reminded Eisenhower that Batista had been a valued Cold War ally. “He outlawed communism in Cuba in 1953. He favored American investments in Cuba and this country generally found bilateral relations with Cuba more satisfactory while Batista was in power.”137 In the meantime, the Eisenhower Administration took a wait-and-see attitude toward the Cuban revolution.
A “consultative committee” of U.S. business interests in Cuba advised Ambassador Earl E. T. Smith that “prompt recognition was necessary to establish [the] most favorable possible climate in which to carry on business.”138 And on January 7, 1959, the United States recognized diplomatically the July 26th Movement–led government in Havana, at the urging of the U.S. business community in Cuba.
Eisenhower outlined U.S. policy in Cuba in a letter to British Prime Minister Harold Macmillan. Eisenhower said his initial response to the revolution was one of “deep skepticism.” He was troubled by the “known radical and anti-American background of the Castro brothers.” But he conceded, “The great popularity which Castro then enjoyed throughout the Hemisphere and the world gave us no alternative but to give him a chance.” He added, “We simply could not afford to appear the bully.”139
Meanwhile, in the aftermath of Castro’s revolution, Batistianos were being publicly executed by revolutionary tribunals, set up hastily with two or three members of the July 26th Movement rebel army and a local resident. There were not enough trained jurists untainted by ties to Batista for professionally staffed tribunals. Defendants found guilty were often promptly executed by firing squads.
On Capitol Hill, liberal Democrats were outraged by the revolutionary tribunals. Senator Wayne Morse of Oregon denounced the “blood baths” occurring in Cuba. On January 12 Morse declared, “I deplore what appears to be the adoption of the old police state technique of kill your enemy.”140 The Eiseinhower Administration refrained from comment.
The editors of the New York Times noted the fall of the Batista regime “was well received in this country.” But the Times warned, “Unhappily, this honeymoon has been punctuated by rifle fire as the execution squads cut down men hastily convicted of outrageous crimes under the Batista regime…. We would appeal to them, not to let butchers and torturers go free, but to try them soberly and according to civil procedures.”141
Rufo López-Fresquet, Cuban treasury minister in 1959, disputed Morse’s claim that the revolutionary tribunals caused “blood baths” in Cuba. López-Fresquet asserted that the tribunals, imperfect as they were, prevented a bloodier “massacre” from taking place.
López-Fresquet recalled bitterly the long silence of the United States about the murder and torture of innocent Cubans during Batista’s reign of terror. Nonetheless, he would defect to the United States in 1960.142
Ruby Hart Philips, veteran New York Times correspondent in Cuba, agreed that the revolutionary tribunals saved lives. “It was apparent… that these masses wanted blood, demanded retribution,” Philips later wrote. “There is no doubt that hundreds of Batista’s supporters would have been torn to pieces in the public plazas had it not been for Castro. Castro himself would have been powerless had he not promised summary trials and executions of the guilty.”143
In retrospect, there was less revenge played out in 1959 than there was when Machado officials were executed in the streets by angry mobs in 1933. Historian Hugh Thomas writes, “At least a thousand were killed and 300 houses were sacked.” When the revolutionary tribunals were shut down in mid-1959, 557 Bastistianos had been executed.144 But Cuba’s revolutionary tribunals and the presence of Batistiano “war criminals” in the United States would continue to roil diplomatic relations between Havana and Washington.
In the lobby of the Hotel Habana Libre, a U.S. journalist asked Fidel Castro about the uproar in the United States over the revolutionary tribunals on January 15, 1959. Would the United States intervene in Cuba? “I am not selling out to the Americans,” Castro replied. “Nor will I take orders from the Americans.”
On January 21, 500,000 Cubans assembled at the Palacio Presidencial in a show of support for the Cuban revolution. When Castro asked the crowd rhetorically if “revolutionary justice” was appropriate for Batista “war criminals,” the answer was “¡Sí, sí!” in what the Times of Havana called “thunderous approval.” Castro demanded the return of the “Cuban war criminals and the money they stole.”145 Havana lodged a formal diplomatic protest with the Eisenhower Administration, demanding the return of the Batistianos to Cuba.146
But the Eisenhower Administration turned a blind eye to the Batistianos streaming into the United States. Assistant Secretary of State Rubottom addressed the diplomatic implications of allowing Batistianos to live in the United States in a memorandum to Secretary of State Christian Herter in December 1959: “Following the fall of the Batista Government… there was a large influx into the United States of officials of the former regime, many of whom have settled in Florida,” Rubottom wrote. “Many Cubans find it increasingly hard to reconcile our professions of friendship for the Cuban people with the continued presence in Florida of persons commonly regarded in Cuba as butchers guilty of unspeakable atrocities against the Cuban people.”147
Meanwhile, President Eisenhower snubbed Castro by refusing to meet with him when he visited Washington in April 1959. Instead, Eisenhower conspicuously left Washington to play golf with friends in Georgia.148 Communist influence in the Cuban revolution was becoming an increasingly controversial topic in the United States.
“We are not Communists,” Castro told the American Society of Newspaper Editors conference in Washington. “Our revolution is a humanistic one.” On NBC’s “Meet the Press,” he said that if there were any Communists in the new Cuban government, “their influence is nothing.” He also touched on another sensitive political issue in Washington—elections in Cuba. He asserted there would be no elections for another three or four years until Cuba’s sweeping economic and social reforms had been completed.149
Castro met with Vice President Richard Nixon and Christian Herter, who had recently replaced the ailing John Foster Dulles. Herter briefed Eisenhower on his meeting with Castro, noting “Castro made a plea for patience while his government tries to deal with the situation in Cuba.” He said Castro did not seem to have a grasp of the magnitude of the problems Cuba faced.150 While Castro was in the United States, the revolutionary regime in Havana continued the process of shutting down the Mafia gambling colony in Cuba.
From the beginning, the July 26th Movement had taken an uncompromising position on the gangster-owned casinos, hotels, and nightclubs. The Fidelistas announced they would shut down the casinos when they came to power. They deplored the corrosive effect of the Mafia colony on traditional Cuban values. Batistianos and the Mafia gamblers had become wealthy by turning Havana into a Caribbean tourist destination for commercialized vices: drugs, gambling, pornographic theaters, and prostitution.151
On January 5, 1959, Meyer Lansky offered an olive branch to the Cuban revolution. “All we know now is that there is a new government in power,” Lansky told the Times of Havana. “We want to do everything possible to cooperate with it.”152
On January 8, Castro referred to the North Americans as “gangsters” in a television interview broadcast in New York. He promised to “clean out all the gamblers who used the influence of Dictator Batista’s regime to build an empire here.” A few days later, the Cuban rebel army took Mafia gambler Nick di Costanzo into custody and interrogated him for nine hours. Di Constanzo was president of the Casino Capri Corporation. Rumors circulated in Havana that the July 26th Movement planned to interrogate Mafia gamblers, causing the gangsters to drop out of sight for the time being.153
A confidential source told the FBI that a group of fifty Mafia gamblers met with Santo Trafficante to discuss what “course” to take. Trafficante told his Florida-based attorney Frank Ragano that he did not plan to leave Cuba. Ragano estimated Trafficante had more than $20 million invested in casinos, hotels, and nightclubs in Cuba in 1959.154 Trafficante minimized the staying power of Castro and the Cuban revolution. “He’s not going to be in office or power for long,” Trafficante told Ragano in 1959. “Batista will return or someone else will replace the guy because there’s no way the economy can continue without tourists, and this guy is closing all the hotels and casinos. This is a temporary storm. It’ll blow over.”155
By order of the Cuban revolution, however, the casinos remained shut down. The Mafia gamblers mounted a campaign to reopen their casinos. Casino and hotel employees organized protests and petition drives to stress gambling’s importance to the Cuban economy. Casinos and hotels employed 27,000 Cubans in 1958, according to the Cuban National Council of Economy.156
Castro had second thoughts. On January 16 he asserted, “We have now arrived at the conclusion that total suppression of gambling would cause the laying off of numerous workers who depend on it to earn a living.” On February 19, the revolution allowed Mafia gaming rooms to reopen after imposing a tax on casinos to fund social programs.157
As a result of the turmoil, however, tourism in Cuba dropped off sharply. Newsweek reported, “Tourists were staying away in droves.” The Cuban Tourist Commission sponsored advertising in the United States to lure tourists back to the island. A low-flying plane trailed a banner over Miami in February announcing, “Casinos Reopen in Havana.” Meanwhile, Lansky shuttled back and forth between Havana and Florida.
Cuban officials suspected that Lansky was manipulating the Hotel Nacional’s books to camouflage the movement of large sums of money out of Cuba. The Riviera claimed unusually large losses of revenue in 1959. The National Bank of Cuba worried that the Mafia gamblers were moving their liquid assets out of Cuba and would default on their loans from the bank.158 The FBI also received reports that Lansky was moving Cuban currency out of Cuba and selling it at a discount to bankers in Miami.”159
In the meantime, the revolutionary regime arrested two of Lansky’s lieutenants. Lansky’s brother Jake and Dino Cellini, who managed the Hotel Riviera casino, were detained for a few days on drug trafficking charges and then released.160
On May 22, 1959, Meyer Lansky contacted the FBI in Fort Lauderdale, Florida. Lansky told the FBI, “The entire [Cuban] government will soon be communistic.” He offered to provide the FBI with additional intelligence about communist activities in Cuba, acknowledging the possible loss of his gambling interests in Cuba had “contributed to his decision to discuss the Cuban situation.”161 The confrontation between the Cuban revolution and the Mafia gamblers would culminate with Trafficante’s arrest.
On June 6, 1959, Cuban authorities arrested Santo Trafficante and Henry Saavedra, who represented Trafficante’s interests at the Hotel Capri. They and other Mafia gamblers—Jake Lansky, Charles “The Blade” Tourine, Tourine’s son Charles de Monico, Guiseppe de George, and Lucien Rebard—were held at the Triscornia immigration prison outside Havana.
Trafficante spoke to his attorney Frank Ragano by telephone after his arrest. Ragano later wrote, “I thought he was trying to bribe his way to freedom, that he still believed the revolutionaries could be bought the same way the Batista bureaucrats had been corrupted…. [H]e was playing for time so as to remain in Cuba as long as possible, to salvage his money, property, and other holdings.”162
A source told the FBI that Trafficante and the other gangsters “lived like kings” at Triscornia, a minimum-security immigration detention center. In an interview with the FBI, Trafficante recalled, “They would let anybody come in,” adding most of his visitors were from Mafia establishments in Havana. He noted, “We would cook, we would have food brought in, we would eat, we would drink…”163
According to a CIA memorandum, Trafficante recruited Sal Morgan, an agent of the Cuban G-2 (military intelligence), to act as a go-between with the Cuban revolution. The memorandum stated, “Subject [Morgan] reports that Trafficante wanted to remain in Cuba and was prepared to cooperate with the Castro government in order to obtain the right to continue business as usual in Havana.”
Trafficante used Morgan in an attempt to bribe G-2 Chief Ramiro Valdés. But Valdés rejected Morgan’s offer. The memorandum reported, “Valdés himself had frequently warned Subject [Morgan] that he was being ‘taken in’ by Trafficante, and that a criminal type like that was not to be trusted.” Valdés told Morgan that Fidel Castro ruled out using Trafficante as an intelligence asset. Castro referred to the Spanish translation of the Mafia gambler’s name, repeating “santo” and “trafficante.” Castro joked, “He is either too much of a saint or too much of a [drug] peddler.”
On August 18, 1959, Trafficante was released from Triscornia. Cuban officials later told the House Select Committee on Assassinations (HSCA) that Cuba had no evidence Trafficante had broken Cuban laws. Ragano asked why Trafficante was being deported. A Cuban official explained: “In the first place he was a Batista supporter… Furthermore, Trafficante is a drug trafficker, and there is no room for drug traffickers under the new government.”
Cuban officials told the HSCA that they detained Trafficante at the request of the U.S. Bureau of Narcotics and Dangerous Drugs (BNDD). The Mafia gambler’s name was on a BNDD list of fifty alleged drug traffickers in Cuba who worked “behind the facade of their gambling operations.” The BNDD had pressed Havana to deport the people on the list in order to break up the Mafia drug trafficking network in Cuba and stem the flow of cocaine and heroin into the United States.164
Although the BNDD pressed Havana to arrest Trafficante, it did not provide sufficient evidence to convict him in court.165 Crime writer Scott Deitche points out that there was a trail of evidence of Santo Trafficante’s Cuba-based drug trafficking that went back to the 1940s. FBI sources reported that casinos in Cuba were used as fronts for heroin traffickers. One FBI report stated, “[C]asinos, while potentially lucrative in themselves, are additionally far more important as fronts for narcotics transactions of large size.”166
A former drug trafficker told the FBI that the Batistianos were complicit in the drug trade. The FBI reported, “It was his opinion that narcotics from Italy to Cuba [arrived] aboard ships that were hauling cargo and passengers… Cuban customs personnel were paid off…”167
Trafficante returned to the United States after his release from the Triscornia. He would maintain a residence in Havana, but he spent most of his time in Florida. He traveled back and forth between Florida and Havana until May 1960, when he settled permanently in Miami.168 Lansky turned bitter when he looked back on his quarter century of gambling in Cuba. “I crapped out!,” Lansky said bluntly.169
Trafficante did not get over the loss of his investments in Cuba either. “I thought we would never stop making all that money in Cuba; those were great times,” Trafficante told Ragano. “Who would have known that crazy guy, Castro, was going to take over and close the casinos?” Trafficante misjudged the U.S. response to the Cuban revolution: “I thought the Marines were going to straighten everything out.”170
Sam Giancana would fly into an uncontrollable rage at the mention of Castro’s name. Giancana’s daughter Antoinette learned not to refer to Castro or Cuba. Giancana yelled at her, “Don’t ever mention that bastard’s name in this house again… ever.” Giancana added furiously, “Do you have any idea of what he’s done to me… to our friends?”
She summed up the significance of the Mafia casinos in Cuba to organized crime families in the United States: “Those casinos were the golden lode whence the profits flowed into the Chicago mob’s treasury—and into the coffers of other crime families across the country. Those losses made Sam a bitter man when the subject of Cuba came up.”171 As the curtain came down on the Mafia gambling colony, Jack Ruby, a Dallas stripclub owner, was on a mysterious “vacation” in Cuba.
Jack Ruby was in Cuba from August 8 until September 11, 1959, according to Cuban tourist cards and U.S. travel records. Four years later, after Ruby gunned down Lee Harvey Oswald, witnesses came forward to the FBI to say that they had seen Ruby at the Tropicana nightclub in September 1959. The Warren Commission questioned Ruby about his stay in Cuba. Ruby said he was in Cuba on vacation in late summer 1959. He spent several nights at the Tropicana, where his friend Lewis McWillie was manager of the casino. He recalled that Martin Fox, one of the Cuban owners of the Tropicana, took him out for a night on the town in Havana. Earlier in the summer Martin, on business in Texas, treated Ruby to dinner in Dallas.
The Warren Commission accepted Ruby’s explanation, concluding that Ruby’s visit to Cuba was “purely social.” Ruby’s explanation invites skepticism, however, given the personalities and circumstances involved. Ruby had ties to organized crime figures first in Chicago and later in Dallas. McWillie was a well-connected gambler. The Tropicana was an epicenter of gangsterismo with connections to Trafficante, as we have seen. And Ruby knew McWillie from Dallas, where McWillie represented the interests of Las Vegas gambler Benny Binion. When McWillie moved to Havana in 1958, he worked closely with Meyer and Jake Lansky, Dino Cellini, and Santo Trafficante.
As manager of the Tropicana’s casino, McWillie worked closely with Martin Fox to move large amounts of money out of Cuba, depositing it in U.S. banks in 1959 and 1960, according to Fox’s widow Ofelia and McWillie’s testimony to the HSCA.
G. Robert Blakey, former general counsel of the HSCA, is among the skeptics. Blakey sees a link between Ruby and Trafficante’s detention. “Trafficante told us that while he was in Triscornia, the Foxes were trying ‘their best to get me out,’” Blakey and his coauthor Richard Billings write.172 They add, “Ruby’s trips to Cuba were an important, but minor, part of an organized-crime operation, which may have had to do with Trafficante’s detention.” The HSCA final report suggested that Ruby was a “courier” for the Mafia gamblers carrying cash between Havana and banks in Miami.
The HSCA report noted that Ruby made at least two trips to Cuba in 1959. Cuban tourist cards indicate that Ruby was in Cuba from August 8 until September 11, when he flew to Miami and returned to Cuba the next day. A day later he flew to New Orleans. FBI and Immigration and Naturalization Service records corroborate Ruby’s trips to Cuba.
Trafficante was released from Triscornia on August 18. There is also evidence that Ruby may have visited Trafficante at Triscornia. John Wilson, a British journalist imprisoned at Triscornia, said that he saw Ruby with Trafficante in 1959. According to a CIA message to President John Kennedy’s National Security Adviser McGeorge Bundy, Wilson told the U.S. Embassy in London that he met a prisoner at Triscornia, “an American gangster gambler named Santos [sic].” The message continued, “While Santos was in prison Wilson says, Santos was visited frequently by an American gangster-type named Ruby.”173
The CIA also suspected some kind of link between Ruby and Trafficante. S. D. Breckinridge, CIA liaison with the HSCA, wrote in a memorandum for the record, “[O]ur study had a few comments on a possible connection between Ruby and Trafficante in 1959, but that we could not take it beyond that.”174 Burt W. Griffin, the Warren Commission’s expert on Ruby, was another skeptic. Griffin questioned the commission’s conclusion that Ruby’s trip Cuba was “purely social.” “Ruby did very few things that were ‘purely social,’” Griffin wrote in an August 1964 memorandum. “In light of the fact that his Cuban visit is tied closely in time to his own interest in selling jeeps to Cuba… I think we should have considerably more information about Ruby’s visit to Cuba before we arrive at such a conclusion.”175
Griffin was referring to the Warren Commission testimony of Ruby’s sister Eva Grant. Grant told the commission that her brother’s trip to Cuba in September 1959 was related to a plan to sell jeeps to Cuba. The Warren Commission reported that in January 1959 “Ruby made preliminary inquiries, as a middle man, concerning the possible sale to Cuba of some surplus jeeps located in Shreveport, Louisiana, and asked about the release of prisoners from a Cuban prison.”176
Ruby contacted Robert McKeown in connection with the jeep sale. McKeown had been arrested for smuggling weapons to Cuba in February 1958. McKeown sold guns for former President Carlos Prío Socarrás to the July 26th Movement.177
McKeown told the FBI that he got a telephone call from “Mr. Rubenstein of Dallas” in January 1959. “Rubenstein” offered him $15,000 to contact Fidel Castro and help arrange the release of three unnamed people from jail in Cuba. McKeown said he could obtain the release of the prisoners but wanted $5,000 in cash before contacting Castro.
Three weeks later, an unidentified man visited McKeown outside of Houston. He said he had an option to buy jeeps in Shreveport, Louisiana, which he wanted to sell to Castro. He wanted McKeown to write a letter of introduction to Castro. McKeown said he would do so for a $25,000 fee. But the visitor did not follow up.
When McKeown saw news photographs of Oswald’s assassin, he realized his visitor was Jack Ruby.178 Ruby corroborated McKeown’s account in an interview with the FBI. Ruby said he telephoned a man, who lived near Houston, about the sale of jeeps to Cuba. The man had been involved in “gun running” to Castro. But the jeep deal fell through.179
The FBI also had evidence linking Ruby to arms shipments to Cuba from Florida in 1959. One of the Bureau’s sources was Blaney Mack Johnson, a Florida gambler. Johnson was a former owner of the Colonial Inn in Hallandale, Florida, one of Meyer Lansky’s “carpet joints” in the Sunshine State.
An FBI memorandum reported, “He [Johnson] stated that Jack Ruby, known then as Rubenstein, was active in arranging illegal flights of weapons from Miami to the Castro organization in Cuba.” The memorandum added, “T-2 [Johnson] stated that one Donald Edward Browder was associated with Ruby in the arms smuggling operations.” Browder was a weapons dealer linked to the Mafia, who sold guns to all sides in Cuba in the 1950s.180
Had the Warren Commission attempted to connect the dots of Ruby’s trips to Cuba and his ties to gangsterismo, it would have opened a Pandora’s box. At a minimum, a thorough investigation of Ruby would have embarrassed the FBI. Ruby was a Bureau informant during the period of his Cuba-related activities. FBI Special Agent Charles Flynn met with Ruby eight times between March and October 1959. FBI Director J. Edgar Hoover explained in a memorandum to the Warren Commission that Ruby “had knowledge of the criminal element in Dallas.”181
The full story of Jack Ruby and Cuba has yet to be told, according to Blakey and Billings. “Our belief that there was something to hide in the Ruby-McWillie relationship was borne out by a remark Ruby made to Wally Weston, a comedian who worked in his nightclub,” Blakey and Billings write. “It was after Ruby had been convicted of murdering Oswald, and they were talking in Ruby’s jail cell. ‘Wally, they’re going to find out about Cuba,’ Ruby said. ‘They’re going to find out about the guns, find out about New Orleans, find out about everything.’”182 With the end of the era of gangsterismo in Cuba, the Mafia gamblers and the Batistianos would regroup in exile.