The Infamous Mob Boss That Killed More People Than Anyone Else | Mafia's Greatest Hits | @RealCrime

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Sam Janana, a powerful mob boss, faced legal repercussions for his involvement in organized crime and CIA assassination plots. After being exiled and attempting a comeback, his death symbolized the decline of organized crime and the shift in the criminal landscape.

Insights

  • Sam Janana, a powerful gangster, rose to prominence by controlling electrician unions and gambling operations in Chicago, showcasing his ability to amass wealth and influence across various sectors.
  • Janana's downfall, catalyzed by Bobby Kennedy's reforms and the FBI's relentless pursuit, emphasizes the diminishing power of organized crime figures like him, signaling a shift in the criminal landscape away from the glamorous associations with show business and politics to a more scrutinized and targeted era by law enforcement agencies.

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Recent questions

  • Who was Sam Janana and what made him infamous?

    Sam Janana was a flamboyant gangster more powerful than Al Capone, known for his extravagant lifestyle and connections with stars like Frank Sinatra. He was involved in organized crime, with the power to kill and order killings, making people fear him with just a stare. Janana excelled in driving killers to their victims, managing money lending, and controlling the electrician union and gambling operations in Chicago. By 1957, he was the boss of the Chicago outfit, with influence in police, courts, and businesses.

  • How did Robert Kennedy impact Sam Janana's criminal activities?

    Robert Kennedy, as Attorney General, began a crusade against organized crime, targeting Janana and the mafia. Despite Janana's involvement in helping John F. Kennedy win the presidency, Kennedy's appointment of Bobby Kennedy intensified the pursuit of Janana. Reforms in the Department of Justice and FBI, including electronic surveillance, gathered incriminating evidence against Janana. His relationship with singer Phyllis Maguire became a vulnerability, closely monitored by FBI agents.

  • What led to Sam Janana's downfall?

    The pressure of surveillance and legal actions took a toll on Janana, leading to outbursts of anger and frustration towards the FBI. He antagonized agents, causing concern from retired boss Accardo. Janana's lucrative business interests in Cuba were disrupted by Castro's regime change in 1959. He suggested poisoning Castro's food and drink, leading to a compromised relationship with the CIA. Janana's imprisonment, contempt of court, and exile from Chicago marked his downfall.

  • How did Sam Janana's death reflect the decline of organized crime?

    Sam Janana's death marked the end of an era, symbolizing the decline of organized crime's glamorous image and its association with show business and politics. The FBI and justice department's actions against the mafia signified a shift in the criminal landscape, highlighting the downfall of once-powerful mob bosses like Janana. His attempt to reestablish influence in the Chicago outfit and subsequent demise showcased the mafia's lack of trust in his silence.

  • What were the repercussions of Sam Janana's past involvement with the CIA?

    Sam Janana faced repercussions from his past involvement with the CIA in assassination plots against Castro. After being deported back to the US, he attempted to reestablish his influence in the Chicago outfit but was met with resistance from a new generation of leaders. Subpoenaed to appear before a senate committee, he was found shot dead in his home, indicating the mafia's lack of trust in his silence.

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Summary

00:00

"Janana: Rise and Fall of Chicago Gangster"

  • Sam Janana, a flamboyant gangster, was more powerful than Al Capone, known for his extravagant lifestyle and connections with stars like Frank Sinatra.
  • Janana was involved in organized crime, with the power to kill and order killings, making people fear him with just a stare.
  • He learned his trade from Capone's enforcers, excelling in driving killers to their victims and managing money lending.
  • Janana's strength lay in his ability to make money, controlling the electrician union and gambling operations in Chicago.
  • By 1957, he was the boss of the Chicago outfit, with influence in police, courts, and businesses.
  • Robert Kennedy, as Attorney General, began a crusade against organized crime, targeting Janana and the mafia.
  • Janana's involvement in helping John F. Kennedy win the presidency led to expectations of government leniency, but Kennedy's appointment of Bobby Kennedy as Attorney General changed the game.
  • Bobby Kennedy's reforms in the Department of Justice and FBI intensified the pursuit of Janana, using electronic surveillance to gather incriminating evidence.
  • Janana's relationship with singer Phyllis Maguire became a vulnerability, closely monitored by FBI agents who exploited it to gather crucial information.
  • The pressure of surveillance and legal actions took a toll on Janana, leading to outbursts of anger and frustration towards the Gmen, ultimately contributing to his downfall.

22:09

Janana's Criminal Saga: From Cuba to Exile

  • Janana antagonized agents and hissed obscenities, causing concern from retired boss Accardo.
  • Janana had lucrative business interests in Cuba, which were disrupted by Castro's regime change in 1959.
  • The CIA sought Janana's help to assassinate Castro due to his connections in Cuba.
  • Janana suggested poisoning Castro's food and drink, leading to a compromised relationship with the CIA.
  • Janana sued the FBI for violating his civil rights with lockstep surveillance, winning an injunction.
  • Janana escaped FBI scrutiny by staying at Sinatra's home and in Las Vegas.
  • The FBI recorded mobster conversations expressing dark sentiments towards the Kennedys.
  • Janana was targeted by lawyer David Shippers, who used a grand jury and immunity to trap him.
  • Janana's refusal to answer questions led to contempt of court and his imprisonment.
  • Janana was stripped of his rank as boss and exiled from Chicago, living in Mexico and continuing his criminal activities.

43:54

Mob boss Janana's downfall signals mafia decline.

  • Sam Janana, a former mob boss, faced repercussions from his past involvement with the CIA in assassination plots against Castro. After being deported back to the US, he attempted to reestablish his influence in the Chicago outfit but was met with resistance from a new generation of leaders. Subpoenaed to appear before a senate committee, he was found shot dead in his home, indicating the mafia's lack of trust in his silence.
  • Janana's death marked the end of an era, symbolizing the decline of organized crime's glamorous image and its association with show business and politics. The FBI and justice department's actions against the mafia signified a shift in the criminal landscape, highlighting the downfall of once-powerful mob bosses like Janana.
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