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Authors: Scott M Dietche

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John Kennedy’s main opponent in the Democratic primaries was Minnesota Senator Hubert Humphrey. Beating Humphrey in Southern states was key, and the primary in West Virginia (a state that was 95 percent Protestant) was seen as a make-or-break vote for Kennedy. It would take a miracle for the New England Catholic to score a win in this unfriendly land. Divine or diabolical intervention was required.

One assassination conspiracy theory places the blame on right-wing oil men in Texas who were not fond of Kennedy’s religion or politics. Some of these shadowy characters also pop up theories involving the Mafia, Lyndon Johnson, and anti-Castro Cuban groups.

The rumor is that Joe Kennedy persuaded Frank Sinatra to ask his “friends” to use their influence to help JFK win the primary. Sinatra approached his pal, Chicago mob boss Sam Giancana. Giancana exerted pressure on the rank and file of the Teamsters and other unions to vote for Kennedy. This may have made the difference. JFK won the primary, Hum-phrey bowed out of the race, and JFK was assured the nomination of the Democratic Party.

One Brief Shining Moment

Kennedy beat Nixon in what was the closest election in history until the 2000 Bush versus Gore contest. And he allegedly had help with it, too. Mobster Sam Giancana, Mayor Richard Daley, and other allegedly crooked politicians in the city of Chicago supposedly stuffed ballot boxes to ensure a Democratic victory. Similar deceit is said to have occurred in Texas. Even with their help, the difference was only about 100,000 votes. John Fitzgerald Kennedy became president.

John Kennedy’s decision to make his brother Robert the attorney general of the United States was a very controversial move. Many Washington insiders despised the Kennedy family, and in their eyes this was just another example of the unrestrained arrogance of the patrician Kennedy clan.

Bobby Kennedy—Double Cross

When Bobby Kennedy was appointed attorney general by his brother, he went after the Mafia in a big way. His two main targets were New Orleans boss Carlos Marcello and Teamsters head Jimmy Hoffa. Bobby made it his mission to take on organized crime, unaware of the serious repercussions his actions may generate. Increasing the federal budget for Mafia busting, the Justice Department under Bobby Kennedy was gearing up for a major battle. In looking at the Mafia-did-it theory, the most popular motive is that the Mafia was not happy with the double cross its members felt they were getting from the Kennedys.

Marcello on the Plane

The first casualty of Bobby’s war on the mob was Carlos Marcello. Marcello had never bothered to become an American citizen. As a result he was subject to deportation. To combat this, he had a bogus birth certificate created that said he was born in Guatemala. He did not want to be returned to Italy or to his actual birthplace, Tunisia, in North Africa. Bobby Kennedy took this opportunity to rid the country of one of its top wise guys. He deported the Cajun don to Guatemala. Marcello was humiliated. He had a terrible ordeal trying to get back into the United States, including being stranded in the Central American jungles by the local military and wandering lost in the rain forests for three days. He was not without influence, however, and eventually made it back to the United States. He sued Robert Kennedy for illegally deporting him. Mafia informants maintain that he spoke openly of killing not the pesky Robert but his brother President John Kennedy.

Hoffa

Robert Kennedy also angered Jimmy Hoffa. The Teamsters president had ties with mobsters from all over the country. He shared a lawyer, Frank Ragano, with Santo Trafficante Jr. In the early 1990s Ragano came out with an unbelievable story. He maintained that he delivered messages from Hoffa to Marcello and Trafficante, setting in motion the plot to kill President Kennedy. Hoffa was a hothead, but he would have had to go through Mafia channels to pull off an assassination this large.

The Havana Connection

Many of the conspiracy theories center on the island nation of Cuba. Located just ninety miles off the coast of Florida, Cuba was a paradise for gamblers and gangsters in the years prior to the Cuban Revolution in 1959. The Mafia was partners with the Batista government, a cruel dictatorship that was very friendly to United States business, both legitimate and illegitimate. Meyer Lansky was the hood who personally dealt with Batista in a mutually beneficial business arrangement. Santo Trafficante Jr. took over his father’s interests in a number of casinos, including the lavish Sans Souci. The Mafia flourished under Batista’s regime, but the peaceful existence was in jeopardy with the rise of Fidel Castro.

In 1959 Fidel Castro won a hard-fought revolution and ousted the Batista regime. While he was fighting the Batista government, Castro was also receiving guns and money from the mob. The gangster casino bosses reasoned that if they supported both sides in the conflict, whichever side won would be eager to do business with them. They made a huge mistake. A former major-league baseball player and one-time seeming friend of the United States, Castro became allied with the Soviet Union after his victory, and the island became a communist enclave, which caused alarm in the U.S. intelligence community. But Castro also kicked out the mobsters and jailed a few of them, including Santo Trafficante Jr.

The Mafia families involved in Cuba included Pittsburgh, Chicago, New York, Kansas City, St. Louis, Cleveland, and Tampa. The role of Tampa was cemented when Ignazio Antinori used his friendships and associations with Cuban politicos to set up a smuggling operation for narcotics as well as raw materials for illicit liquor production during Prohibition.

Bay of Pigs

Before Kennedy became president, there were plans to invade Cuba and oust Castro. It would not be an attack by American armed forces, however; instead the assault would come from exiled Cubans who had planned and trained in the United States with the help of the CIA and the Mafia, who helped staff the operation with Cuban gangsters. Kennedy did not veto the plan when he took office, but when it was launched, he refused, at the last minute, to aid the assault with air cover from the United States Air Force. It was a total disaster, and thousands of exiled Cubans were killed or captured. Those taken alive probably came to wish that they had died on the beach.

Kennedy made many enemies in many circles by his refusal to provide air support in the Bay of Pigs invasion. He earned the hatred of the Cubans who wanted their nation back, those in the CIA who felt betrayed and humiliated, American big business, which had enjoyed great profits in Cuba, and, of course, the Mafia, for whom Cuba was once a cash cow and pleasure palace. Many of the Cubans who felt betrayed by the Kennedy administration drifted into covert operations run by the CIA out of Miami.

After he was released from Cuban prison, Santo Trafficante Jr. settled in Miami, where he led a crew of Cuban gangsters who left Cuba in 1959. This group conducted gambling operations, drug trafficking, loanshark-ing, and anti-Castro activities.

Jack Ruby

Mere hours after JFK’s murder, lone oddball Lee Harvey Oswald was picked up for the murder. With forty years of hindsight, many people feel it was all too convenient, a neat and tidy solution to the murder. Making things especially tidy was Oswald’s murder in the Dallas Police headquarters by a local strip club owner and small-time hoodlum, Jack Ruby.

Ruby burst out of the crowd and shot Oswald, thus ending the possibility of a trial in which potentially explosive information might have come to light. Ruby claimed his reason was the desire to spare first widow Jackie Kennedy the pain and suffering of a protracted trial, where she would have to relive the horrific event over and over. There appears to have been more to the story, however.

Chicago Youth

During his youth, Ruby was a runner for the Chicago Outfit. He sold horseracing sheets and was involved in bookmaking. There are some rumors that Ruby actually worked for Al Capone. While he was making the rounds on the street he became friendly with David Yaras and Lenny Patrick, two hoods that became high-level operatives in the Outfit. Ruby also became involved in the Teamsters Union, where he was suspected in the murder of a union rep.

Jack Ruby

Courtesy of AP Images

Jack Ruby, charged with the slaying of Lee Harvey Oswald, the accused assassin of John F. Kennedy, is surrounded by photographers and reporters before the start of his change of venue hearing in Dallas, Texas, Feb. 10, 1964. Seated with Ruby are two of his attorneys, Joe Tonahill, left, of Jasper, Texas, and Melvin Belli, right, of San Francisco.

BOOK: The Everything Mafia Book
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