Sam Giancana

• 1. Introduction

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  Sam Giancana, who once ran the Chicago Outfit, died on the night of the 19th of June 1975 in the basement kitchen of his house in Oak Park, Illinois. At around 11 p.m., his caretaker, Joseph DiPersio, found the body on the floor. A gunman had come in through the basement and shot Giancana seven times in the head and neck with a .22-caliber pistol. He was said to have been frying sausage and peppers when the killer arrived. Only a week earlier, he had undergone gall bladder surgery in Houston. In a few days he was due to sit before the Church Committee of the US Senate. The committee was investigating Mafia involvement in CIA plots to kill Cuban leader Fidel Castro. Who needed this man silent? How did a Chicago gangster come to be working beside American spies? And what did he really have to do with the career of a young senator from Massachusetts? To answer those questions, the story begins nearly seven decades earlier, on a crowded street in Chicago.

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• 2. The Patch and the 42

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  Antonio Giangana and Antonia DeSimmona came from Castelvetrano, Sicily, and their son Gilormo was born in Chicago's Patch neighborhood on the 24th of May 1908. His father had immigrated in 1905 and his mother in 1906. The boy grew up among seven siblings. His mother died in 1910, and his father then married a woman named Mary Leonardi. As a teenager, Giancana joined the 42 Gang, a juvenile street crew that worked for political boss Joseph Esposito. The name was a joke on Ali Baba and the 40 Thieves. The boys believed they were one better. Giancana earned a reputation as an excellent getaway driver, a big earner, and a vicious killer. Esposito was murdered, and Giancana was allegedly involved. Afterward the gang became a de facto extension of the Chicago Outfit, whose leaders included Frank "the Enforcer" Nitti, Paul "the Waiter" Ricca, and Tony "Joe Batters" Accardo. Police first arrested Giancana in 1925 for auto theft. He soon graduated to "triggerman." By the age of 20 he was the prime subject of three murder investigations, though he was never tried for any of them. In 1929 he was convicted of burglary and larceny and sentenced to one to five years in the Joliet Correctional Center. He was released in 1932 after serving three years and nine months. During the late 1930s he became the first 42er to join the Outfit itself. From the early 1940s through the 1950s, he controlled gambling, liquor distribution, and political rackets in Louisiana through his longtime friend H. A. Killian. Killian's power over liquor licenses came from his ties to New Orleans associate Carlos Marcello. In 1939 Giancana was convicted of bootlegging and sentenced to four years, which he served at Leavenworth and at Terre Haute. When he walked out in 1942, he already had a scheme in mind for Chicago's South Side.

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• 3. Climbing the Outfit

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  Accardo, then the Outfit's underboss, listened in 1942 as Giancana urged him to seize the payout system of the South Side's African American "policy" lottery. Giancana's crew is believed to have persuaded gambling boss Eddie Jones to quit his racket and leave the country. Theodore Roe, another major South Side boss, refused the Outfit's demand to hand over his operation. On the 19th of June 1951, Roe fatally shot Leonard "Fat Lennie" Caifano, a made man in Giancana's crew. Giancana's crew was held responsible for Roe's murder on the 4th of August 1952. The takeover was not finished until Jackie "the Lackey" Cerone frightened "Big Jim" Martin into fleeing to Mexico. Cerone had put two bullets in Martin's head, and neither killed him. Afterward the game was producing millions of dollars a year for the Outfit. That windfall is believed to have been a major reason Giancana was anointed boss in 1957. The title came with strings. Accardo joined Ricca in semi-retirement as consigliere, yet everyone understood the two older men held the real power. Giancana had to consult them on every important matter. That same year he attended the Mafia's Apalachin meeting at the Upstate New York estate of Joseph Barbara. A wiretap later caught Buffalo boss Stefano Magaddino and Giancana agreeing the gathering belonged near Chicago. Giancana boasted that the area was "the safest place in the world" because he had several police chiefs on his payroll. Associate Hyman Larner helped extend the Outfit's gambling and smuggling to Panama and Iran. The Miami operation's headquarters moved to Panama, where local banks made laundering money easier. The Outfit ran these operations in partnership with the CIA. By 1966 the partnership had grown into arms smuggling to the Middle East for Israel's Mossad. Richard Cain, a corrupt police officer, served as Giancana's courier and financial adviser, making frequent trips to Mexico. In 1959 Giancana faced the Select Committee on Improper Activities in Labor and Management. When he began laughing under questioning, Chief Counsel Bobby Kennedy snapped, "I thought only little girls giggled, Mr. Giancana."

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• 4. The Kennedy Election Claims

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  "I help get Jack elected and, in return, he calls off the heat." That is the line Chuck Giancana, a relative, attributed to Sam Giancana in the book Double Cross. Some journalists have claimed that Giancana and his Chicago syndicate played a role in John F. Kennedy's victory in the 1960 presidential election. Judith Exner, Giancana's mistress, and Tina Sinatra, Frank Sinatra's daughter, both said he used his connections to persuade unions to back Kennedy. Exner added that Giancana bragged Kennedy would never have won without him. The bargain, if it existed, did not hold. Attorney General Robert F. Kennedy launched a serious crackdown on organized crime. Giancana is alleged to have come to regret his help. Frank Ragano, the lawyer for Tampa boss Santo Trafficante Jr., said Giancana complained to Trafficante that the mob had broken their backs to give Kennedy the election. In return, Giancana grumbled, Kennedy had his brother hound them to death. The president's brother would soon appear again in Giancana's story, this time as the official who protected a CIA operation.

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• 5. The Plot Against Castro

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  In September 1960, the CIA sent ex-FBI agent Robert Maheu to meet Johnny Roselli, the Chicago mob's West Coast representative and Giancana's number-two man. Maheu hid who had sent him and presented himself as an advocate for international corporations that Castro was expropriating. He offered $150,000 for the "removal" of Castro. Roselli refused to take any pay. He introduced Maheu to two men he called Sam Gold and Joe. Sam Gold was Giancana, and Joe was Trafficante, one of the most powerful mobsters in Cuba before the revolution. The logic was simple. After Castro toppled Fulgencio Batista in 1959, the CIA wanted a partner as worried about him as the agency was, and the Mafia had lucrative investments in Cuban casinos. Giancana's own daughter, Antoinette, recalled his fury at Castro. When she once voiced admiration for the Cuban leader, he asked whether she had any idea what Castro had done to him and to their friends. Giancana suggested poison pills for Castro's food and drink. The CIA handed the pills to Juan Orta, Giancana's nominee, whom he presented as a corrupt official in the new Cuban government with access to Castro. After six attempts to introduce the poison, Orta abruptly demanded to be relieved and passed the job to an unnamed participant. Giancana and Trafficante then tried again through Tony Verona, commander of the Cuban Exile Junta. Verona asked for $10,000 in expenses and $1,000 worth of communications equipment. How much work followed is unknown, because the Bay of Pigs invasion in April 1961 ended the program soon after. Giancana reportedly said the CIA and Cosa Nostra were "different sides of the same coin." Exner claimed she carried messages about Castro between Giancana and Kennedy, whom she said she also saw as a lover. Antoinette Giancana offered a different reading, saying her father was running a scam to pocket millions of CIA dollars. Documents released in 1997 and 2007 confirmed that mobsters did work with the CIA against Castro. Hearings of the Church Committee had already partly corroborated the story, and that is why the committee wanted Giancana's testimony.

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• 6. Women and Scandal

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  On the 23rd of September 1933, Giancana married Angeline DeTolve, whose parents had emigrated from the Italian region of Basilicata. The couple lived in a Chicago neighborhood called The Island. They had three daughters: Antoinette in 1935, Bonnie Lou in 1938, and Francine in 1945. That same year they bought the house in Oak Park. Angeline died on the 23rd of April 1954, leaving Giancana to raise the girls alone. Newspapers called him by the nickname "Momo," from a slang word for a madman. To his wife he signed a card with a gentler name, "Mooney." Later his romantic life became public. Frank Sinatra introduced him to Phyllis McGuire of the McGuire Sisters, and the two carried on a long-lasting affair. Giancana suspected her of seeing comedian Dan Rowan and asked Maheu to wire her room. The agent assigned to plant the device was arrested before he could do it. Robert F. Kennedy blocked prosecution of both the agent and Maheu at the CIA's request. Antoinette Giancana says McGuire carried on a concurrent affair with the president himself. In the summer of 1963, Giancana stayed with McGuire in a chalet at the Cal-Neva Lodge while her group performed in its Celebrity Room. The scandal cost Sinatra his ownership of the Cal-Neva and his part ownership of the Sands Hotel. Antoinette later wrote her father's biography, Mafia Princess. The 1995 HBO film Sugartime portrayed the romance with McGuire, with John Turturro as Giancana.

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• 7. Silence and Flight

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  On the 1st of June 1965, a grand jury summoned Giancana and granted him immunity. He stayed silent anyway. His lawyer, Edward Bennett Williams, had urged him to talk. Giancana ignored the advice because he did not believe he would be punished after helping the CIA try to kill Castro. The judge jailed him for contempt of court for more than a year, the length of the grand jury's term. While he sat in a cell, his masters in the Outfit decided he was no longer worth protecting. Ricca and Accardo deposed him as operational boss and replaced him with Joseph "Joey Doves" Aiuppa. After his release in 1966, Giancana fled to Cuernavaca, Mexico, to avoid further grand jury questioning. He lived there for years. Mexican authorities arrested him on the 19th of July 1974 and deported him to the United States. He arrived back in Chicago on the 21st of July 1974, less than a year before his death.

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• 8. Who Killed Sam

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  After Giancana came home, police detailed officers to guard his house in Oak Park. They could not stop what happened that June. Dominic "Butch" Blasi, a longtime associate, was with Giancana on the night of the murder, and police questioned him as a suspect. Neither the FBI nor Antoinette Giancana believes Blasi did it. In the 2000s, hitman Nicholas Calabrese told the FBI that Tony Accardo was part of the killing. He also said Angelo LaPietra got rid of the gun, which carried a suppressor made by Frank Calabrese Sr. and Ronnie Jarret. One explanation points south to Trafficante. He may have ordered the murder out of fear of what Giancana would tell the Senate. That would have required permission from Accardo and Aiuppa. Giancana's death coincided with the discovery of Roselli's decomposing remains in an oil drum floating off Miami. He had been shot and chopped up before being dumped in the sea. Some suspected Trafficante ordered that killing too, and Antoinette Giancana considers this the likely reason for her father's murder. Rumors also pointed at the CIA. Former CIA Director William Colby said, "We had nothing to do with it." During a deposition, John Whitten said he suspected William Harvey, a CIA assassin who was in the area. Days after the murder, Michael J. Corbitt, police chief of Willow Springs, Illinois, heard a different account from Outfit capo Salvatore Bastone. Bastone said Giancana had championed Tony Spilotro, who lived nearby and visited the house often. Asked for the reason behind the killing, Bastone replied that there was never just one. Then he added a warning: "Let's just say that Sam should've remembered what happened to Bugsy Siegel."

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