Sam Giancana: The Mob Boss Connected to the Kennedys | History Hit

Sam Giancana: The Mob Boss Connected to the Kennedys

Sam Giancana, boss of the 'Chicago Outfit', leaving the Federal Building at Foley Square in New York City in 1965.
Image Credit: The Protected Art Archive / Alamy Stock Photo

Nicknamed ‘Momo’ from the slang term ‘Mooney’, meaning crazy, Sam Giancana was the boss of the infamous Chicago Outfit from 1957 to 1966. He had joined the mob as a young man, working under Al Capone, before eventually taking over the criminal enterprise.

Known for his unstable behaviour and hot temper, Giancana rubbed shoulders with everyone from dangerous underworld criminals to high-profile figures such as Phyllis McGuire, Frank Sinatra and the Kennedy family.

Giancana’s rise to power is as sensational as his reputation: born in New York to Italian immigrant parents, he climbed through the ranks of the Chicago underworld and was later recruited by the CIA in a plot to assassinate Cuban leader Fidel Castro. After the assassination of President John F. Kennedy in 1963, some suggested Giancana had been involved as payback for the president’s crackdown on organised crime.

A man of many faces, Sam Giancana remains a fascinatingly difficult figure to pin down. Here’s an introduction to the infamous mobster.

A violent upbringing

Gilorma ‘Sam’ Giancana was born into a Sicilian immigrant family in Chicago in May 1908. His father was known to beat him severely. Renowned for truancy as a child, Giancana was expelled from his elementary school and sent to a reformatory. He joined the notorious 42 Gang when he was just a teenager.

Giancana served prison time for several offences such as car theft and burglary, with many biographies stating that he was arrested more than 70 times throughout his life. Police believe that by the time he was 20, Giancana had committed 3 murders.

Giancana’s connections were powerful: in 1926, he was arrested and charged with murder but was not tried, likely because the key witnesses kept ending up dead. By the end of the 1930s, Giancana graduated out of the 42 Gang and into Al Capone’s Chicago Outfit.

Joining the Chicago Outfit

Giancana started working for mob boss Al Capone after meeting him in a brothel. Giancana was responsible for distributing whiskey in Chicago during the Prohibition, and due to being in good favour was quickly nicknamed ‘Capone’s Boy’.

Chicago Outfit boss Al Capone, who took Giancana under his wing, pictured in 1930.

Image Credit: Wikimedia Commons / Public Domain

He eventually controlled the majority of the illegal gambling and liquor distribution rackets in Louisiana, and also had a hand in many political rackets. In 1939, he was convicted of bootlegging, for which he served 4 years in prison.

After his release from prison, Giancana made a number of tactical (and often violent) manoeuvres which strengthened the Chicago Outfit’s criminal position.

By the 1950s, long after Capone’s reign of terror, Giancana was recognised as one of the leading mobsters in Chicago. In 1957, the Chicago Outfit’s top man, Tony ‘Joe Batters’ Accardo, stepped aside and named Giancana as his successor.

An obsession with politics

Giancana took a keen interest in politics and was involved in many political rackets. In addition, he had figures such as police chiefs on his payroll.

His political and police connections were symbiotic. For instance, in 1960 he was involved in talks with the CIA about a plot to assassinate Cuban leader Fidel Castro, who had forced the mob out of Cuba after his 1959 revolution.

Fidel Castro speaking in Havana, Cuba, 1978.

Image Credit: CC / Marcelo Montecino

The Kennedy connection

During John F. Kennedy’s election campaign in 1960, Giancana’s influence in Chicago was called upon to help Kennedy defeat Richard Nixon in Illinois. Giancana pulled some strings with his local connections and reportedly swung the balance of the election. Around the same time, in 1960, Giancana and President John F. Kennedy are thought to have unknowingly shared the same girlfriend, socialite Judith Campbell.

Ultimately, Giancana’s interference with the election didn’t work in his favour: one of President John F. Kennedy’s first actions upon taking office was to appoint his brother Robert Kennedy as attorney general. And one of Robert’s main priorities was to go after the mob, with Giancana therefore becoming a prime target.

After the mob’s support of Kennedy’s political campaign, this was perceived by the mob as both a betrayal and a huge threat to their power.

John F. Kennedy’s assassination

On 22 November 1963, President John F. Kennedy was assassinated in Dallas. Rumours quickly began to circulate that Giancana, along with a number of other gang bosses, were at the helm of the crime.

The Warren Commission, which investigated the assassination, famously concluded that Kennedy was killed solely at the hands of leftist loner Lee Harvey Oswald. However, rumours about mob involvement were rife.

In 1992, the New York Post reported that a number of mob bosses had been involved in the assassination. It was claimed that labour union and criminal underworld leader James ‘Jimmy’ Hoffa ordered some mob bosses to plan to kill the President. Mob lawyer Frank Ragano apparently told some of his associates, “you won’t believe what Hoffa wants me to tell you. Jimmy wants you to kill the president.”

Fredrik Logevall joined me on the pod to discuss the life and legacy of John F. Kennedy. By the time of his assassination in 1963, John F. Kennedy stood at the helm of the greatest power the world had ever seen. Born in 1917 to a striving Irish-American family that had ascended the ranks of Boston's political machine, Kennedy was bred for public service and he rose meteorically to become America's youngest president.
Listen Now

Killed for his silence

In 1975, a committee set up to monitor government intelligence activities discovered that Giancana and President John F. Kennedy had simultaneously been engaging with Judith Campbell. It emerged that Campbell had been delivering messages from Giancana to Kennedy over the course of the 1960 Presidential election, and that they later contained intelligence concerning the plans to murder Fidel Castro.

Giancana was ordered to appear before the committee. However, before he could appear, on 19 June 1975, he was murdered in his own home while cooking sausages. He had a huge wound on the back of his head, and had also been shot 6 times in a circle around his mouth.

It is widely believed that fellow mob figures from New York and Chicago families ordered the hit on Giancana, likely because the information he was being ordered to provide broke the mafia code of silence.

The mysterious circumstances of Giancana’s death form only a fragment of a life riddled with unanswered questions. However, his links to President John F. Kennedy, Judith Campbell and the plot to assassinate Fidel Castro have cemented Giancana as a central figure in the infamous legacy of the mob.

Lucy Davidson