37 Facts About Sam Giancana

Early Life and Rise in Crime

Sam Giancana's journey from a troubled childhood to a feared mob boss is filled with intrigue and violence. Let's delve into his early years and ascent in the criminal world.

1. Birth and Early Life: Born Salvatore Giancana on May 24, 1908, in Chicago, Illinois, he was the son of Sicilian immigrants. His mother died when he was just two, leaving him with a brutal father who was a produce peddler.

2. Street Gangs: As a young boy, Giancana joined the 42 Gang, a notorious group involved in petty crimes. This gang served as his entry point into the world of organized crime.

3. Career in Organized Crime: Giancana started as a getaway driver for Al Capone. By 20, he had become a "triggerman," implicated in several high-profile murders, including the infamous St. Valentine's Day Massacre of 1929.

4. Arrests and Imprisonment: Throughout his career, Giancana was arrested over 70 times for various offenses, including auto theft, operating an illegal still, and burglary. He served multiple jail terms.

Leadership in the Chicago Outfit

Giancana's rise to power within the Chicago Outfit marked a significant chapter in his life. His leadership style was ruthless and effective.

5. Leadership in the Outfit: In 1957, Tony Accardo stepped down as the leader of the Chicago Outfit, and Giancana took over. He consolidated control over Chicago's illegal lottery rackets through violent means.

6. National Summit Participation: That same year, Giancana represented the Chicago Outfit at the national summit of Mob bosses in Apalachin, New York, a significant event in Mafia history.

Personal Life and Relationships

Giancana's personal life was as colorful as his criminal career, filled with notable relationships and affairs.

7. Personal Life: Giancana married Angeline DeTolve in 1933, and they had three daughters. Their daughter Antoinette later wrote a memoir titled Mafia Princess in 1984.

8. Psychological Profile: During World War II, Giancana was classified 4-F (unfit for military service) due to his strong anti-social tendencies. A psychologist described him as a "constitutional psychopath."

9. Counterfeit Gas Ration Stamps: During the war, Giancana manufactured counterfeit gas ration stamps, further entrenching his criminal activities.

10. Policy Kings: He played a significant role in the Mob's takeover of Chicago's African-American illegal lottery, known as "policy," boosting the Mob's income by millions through violent means.

Notable Crimes and Connections

Giancana's criminal activities and connections with celebrities and politicians added layers to his already complex persona.

11. Teddy Roe Murder: In 1952, Giancana's crew killed Teddy Roe, a South Side "Policy King," as part of their efforts to control the numbers racket.

12. Frank Sinatra Connection: Giancana was friends with show-business personalities, including Frank Sinatra, who gifted him a sapphire pinky ring, one of his signature accessories.

13. Judith Campbell Exner: Giancana had a romantic relationship with Judith Campbell Exner, who was also involved with President John F. Kennedy, fueling theories about his involvement in the JFK assassination.

14. Phyllis McGuire Affair: He also had an affair with Phyllis McGuire of the McGuire Sisters, further highlighting his reputation for infidelity.

Decline and Exile

Despite his power, Giancana's high-profile activities eventually led to his downfall and exile.

15. Mob Boss Succession: After Tony Accardo stepped down, Giancana became the leader of the Chicago Outfit. However, Accardo maintained considerable influence even in retirement.

16. Las Vegas Investments: Giancana invested in Las Vegas casinos and off-shore operations in Iran, the Caribbean, and Great Britain, expanding the Outfit's financial reach.

17. Loss of Control: In 1967, the national Mob Syndicate removed Giancana from his position due to his high-profile activities and the subsequent media attention.

18. Exile in Mexico: After losing control of the Outfit, Giancana moved to Mexico to avoid further U.S. government inquiry. He lived in self-imposed exile until 1974.

Return and Mysterious Death

Giancana's return to the U.S. and his subsequent murder remain shrouded in mystery and speculation.

19. Return to Testify: In 1974, Giancana returned to the United States to testify before a grand jury investigating Mafia involvement in a CIA plot to assassinate Fidel Castro. He was granted immunity from federal prosecution for his testimony.

20. Scheduled Testimony: Before his scheduled testimony before the United States Senate committee investigating Mafia involvement in the CIA plot, Giancana underwent gall bladder surgery in Houston, Texas. He returned to his Oak Park home on June 17, 1975.

21. Murder: On June 19, 1975, Giancana was shot seven times in the head and neck while cooking in his basement kitchen. The murder remains unsolved, with various theories suggesting involvement by rival Mafiosi, CIA operatives, or one of his former girlfriends.

22. Investigation and Speculation: The investigation into Giancana's murder was extensive, but no one was ever charged. Speculation included theories about Tony Spilotro, a young Outfit member who would later become infamous in Las Vegas.

Legacy and Cultural Impact

Giancana's life continues to captivate the public through various media portrayals and cultural references.

23. Legacy in Media: Giancana has been portrayed in numerous films and books, including Sugartime (1995), Power and Beauty (2002), and King Kennedy (2012). He remains a central figure in the history and legends of the Mob.

24. Biographical Works: Giancana is the subject of several biographies, including Mafia Princess by his daughter Antoinette and Double Cross: The Explosive, Inside Story of the Mobster Who Controlled America by his brother Chuck Giancana and his godson Sam Giancana.

25. Literary Depictions: Giancana is a major character in novels such as Chicago Confidential and Road to Paradise by Max Allan Collins, and American Tabloid and its sequels by James Ellroy.

26. Music References: The rapper Kool G Rap named his album The Giancana Story (2002) after Sam Giancana, and Giancana is mentioned in songs like "Edge" by Shyne and "Dope money" by The Lox.

27. Cultural Impact: Despite his notorious reputation, Giancana was described by some as a "model citizen" who kept to himself in his Oak Park neighborhood. His colorful personality and flamboyant lifestyle, including driving a pink Cadillac and wearing dapper sharkskin suits, have become part of his enduring cultural image.

28. Family Mausoleum: Giancana was interred in the family mausoleum at Mount Carmel Cemetery in Hillside, Illinois, next to his wife Angeline, who had died in 1954.

29. Mobster Reputation: Giancana was reputed to have ordered at least 100 gangland executions during his career, solidifying his reputation as a ruthless mob boss.

30. CIA Involvement: Theories abound about Giancana's involvement with the CIA, particularly regarding the plots to assassinate Fidel Castro. His testimony before the Senate committee was scheduled to reveal more about these activities, but he was murdered before he could provide any significant information.

31. Kennedy Assassination Theories: Giancana's connections to the Kennedys, particularly through Judith Campbell Exner, have led to numerous conspiracy theories surrounding his potential involvement in the assassination of President John F. Kennedy.

32. Tony Spilotro Connection: There is speculation that Tony Spilotro, a young Outfit member, might have been involved in Giancana's murder. Spilotro went on to become infamous in Las Vegas for his involvement in various mob activities.

33. Witnesses and Suspects: Despite extensive investigations, no one was ever charged with Giancana's murder. Theories include involvement by rival Mafiosi, CIA operatives, or one of his former girlfriends.

34. Personal Habits: Giancana was known for his distinctive personal habits, including smoking Cuban cigars and talking out of the side of his mouth. He also wore an alligator shoe and a sapphire pinky ring, gifts from Frank Sinatra.

35. Neighborhood Perception: Despite his notorious reputation, Giancana's neighbors in Oak Park described him as a quiet man who kept to himself. This contrast highlights the complex nature of his public and private lives.

36. Historical Significance: Giancana's life and career are significant not only for his role in organized crime but also for the broader historical context of the American Mafia and its interactions with politics and celebrity culture.

37. Enduring Legacy: Sam Giancana's legacy continues to fascinate audiences through literature, film, and popular culture. His life remains a testament to the enduring power and intrigue of the American Mafia.

The Enduring Legacy of Sam Giancana

Sam Giancana's life was a whirlwind of crime, power, and intrigue. From his early days in Chicago's Little Italy to his rise as a feared mob boss, Giancana left an indelible mark on American history. His connections with celebrities like Frank Sinatra and his rumored involvement with the CIA and the Kennedy assassination only add layers to his mystique. Despite his violent methods, some saw him as a quiet neighbor, highlighting the duality of his existence. His unsolved murder in 1975 remains a tantalizing mystery, fueling endless speculation. Giancana's story, filled with drama and danger, continues to captivate the public imagination. His life serves as a testament to the complex world of organized crime and its far-reaching impact. Sam Giancana may be gone, but his legacy lives on, forever etched in the annals of American Mafia lore.