Chicago has long been infamous for its ties to organized crime, particularly during the Prohibition era. The city became a stronghold for notorious mobsters who controlled the illicit liquor trade, gambling, and other criminal activities. In this article, we’ll explore the lives of some of the most famous mobsters from Chicago, detailing their crimes, arrests, the legal statutes they violated, and how the legal system handled their cases.

1. Al Capone

Nickname: Scarface
 Era: 1920s-1930s
 Crimes: Bootlegging, tax evasion, murder
 Arrest: 1931
 Laws Violated:

  • 18 U.S.C. § 371: Conspiracy to defraud the United States (tax evasion)
  • Internal Revenue Code of 1926: Tax evasion
  • Illinois State Law: Murder and organized crime-related activities

Story: Al Capone is perhaps the most iconic mobster in American history. He rose to prominence by controlling Chicago’s illegal liquor trade during Prohibition, earning millions while bribing politicians and law enforcement. Despite his involvement in violent crime, including the infamous St. Valentine’s Day Massacre, the federal government struggled to arrest him for murder. Instead, he was finally convicted of tax evasion in 1931. His criminal empire unraveled when the federal government employed forensic accounting to trace his unreported income.

Legal Perspective: The government’s decision to pursue Capone for tax evasion, rather than violent crimes, marked a critical legal strategy in organized crime cases. By leveraging the Internal Revenue Code of 1926, federal prosecutors bypassed traditional criminal charges, focusing on financial crime—a tactic still used against organized crime today. Capone’s defense attorney, George E. Q. Johnson, argued for a lesser sentence based on medical grounds, but Capone still served 11 years.

2. Frank Nitti

Nickname: The Enforcer
 Era: 1930s-1940s
 Crimes: Extortion, bootlegging, conspiracy
 Arrest: 1943
 Laws Violated:

  • Sherman Antitrust Act: Forcing movie companies to pay protection money
  • Hobbs Act (18 U.S.C. § 1951): Extortion by violence or threat
  • Illinois State Law: Various criminal activities related to organized crime

Story: Frank Nitti was Al Capone’s trusted lieutenant and took over the Chicago Outfit after Capone’s imprisonment. Nitti was instrumental in expanding the mob’s control over labor unions and the movie industry, using extortion and violence. In 1943, Nitti and other Outfit members were indicted for extorting the Hollywood movie industry. Facing pressure from federal prosecutors and the prospect of serving a long prison sentence, Nitti died by suicide before his trial.

Legal Perspective: The use of the Hobbs Act in Nitti’s case showcased federal prosecutors’ ability to tackle organized crime through extortion laws. The statute allows for severe penalties against those who obstruct or affect commerce through violence or coercion. Nitti’s case served as a key precedent in future mob prosecutions, highlighting the intersection of criminal and labor law. 

3. Sam Giancana

Nickname: Momo
 Era: 1950s-1960s
 Crimes: Racketeering, gambling, conspiracy
 Arrest: 1965 (though never convicted)
 Laws Violated:

  • Racketeer Influenced and Corrupt Organizations Act (RICO) – 18 U.S.C. §§ 1961–1968: Engaging in racketeering activity
  • Federal Wire Act (18 U.S.C. § 1084): Interstate gambling violations
  • Illinois State Law: Illegal gambling operations

Story: Sam Giancana was a powerful leader of the Chicago Outfit during the 1950s and 60s, deeply involved in illegal gambling, labor racketeering, and possibly political corruption. His ties to political figures, including potential connections to the Kennedy family, made him one of the most influential crime bosses of his time. Giancana was eventually subpoenaed to testify before a grand jury but was never convicted of any major crime. His silence in front of the grand jury (protected by the Fifth Amendment) helped him avoid serious prison time.

Legal Perspective: Giancana’s legal battles were significant in that they highlighted the complexities of prosecuting organized crime figures under RICO laws. Though RICO became a powerful tool for the federal government in later decades, Giancana’s avoidance of conviction was largely due to his ability to exploit legal protections, such as refusing to testify under the Fifth Amendment. His defense attorneys skillfully navigated these legal loopholes, allowing him to evade incarceration for much of his life.

4. Tony Accardo

Nickname: Joe Batters
 Era: 1940s-1980s
 Crimes: Murder, racketeering, extortion
 Arrest: Never formally convicted
 Laws Violated:

  • 18 U.S.C. § 1952: Interstate racketeering (Travel Act)
  • RICO (18 U.S.C. §§ 1961–1968): Engaging in organized crime activities
  • Illinois State Law: Multiple organized crime-related offenses

Story: Tony Accardo, known as Joe Batters for his brutal efficiency in enforcing the mob’s rules, became the de facto leader of the Chicago Outfit after Frank Nitti’s death. Under his reign, the Outfit expanded into various illicit operations, including gambling, loan-sharking, and labor racketeering. Accardo’s most remarkable feat was his ability to avoid conviction despite decades of being linked to organized crime. Even though he faced multiple indictments and investigations, none led to serious jail time, a testament to his legal defense team.

Legal Perspective: Accardo’s success in evading jail highlights the importance of skilled legal defense in organized crime cases. His attorneys were able to challenge evidence, question the credibility of witnesses, and exploit procedural errors to keep Accardo out of prison. Despite multiple investigations under RICO and the Travel Act, Accardo’s defense team often shielded him from direct legal consequences by weakening the government’s case. “More modern legislature has been put into place to ensure Chiago’s safety,” shares Chicago criminal defense lawyer David Drwencke.

5. John “Jackie the Lackey” Cerone

Era: 1950s-1980s
 Crimes: Racketeering, extortion, conspiracy
 Arrest: 1986
 Laws Violated:

  • RICO (18 U.S.C. §§ 1961–1968): Engaging in organized crime activities
  • Labor Management Relations Act (29 U.S.C. § 186): Corruption and bribery related to labor unions
  • Illinois State Law: Extortion and violent crime

Story: John Cerone was another influential member of the Chicago Outfit, serving as an underboss and later acting boss. Cerone was involved in various labor racketeering schemes, where the Outfit controlled union activities through bribery and coercion. He was arrested and convicted under RICO statutes in 1986 for his role in overseeing a massive illegal gambling operation.

Legal Perspective: Cerone’s conviction under RICO marked a significant victory for federal prosecutors, as they were able to use the broad scope of the statute to charge him for various acts committed over decades. The Labor Management Relations Act was also key in this case, as it was used to expose the corruption within unions that the Outfit controlled. Cerone’s defense attempted to challenge the scope of the RICO charges, but the government’s use of wiretaps and financial records proved to be too much to overcome.

Nobody Is Above The Law

Chicago’s most notorious mobsters left a lasting impact on both the city’s history and the American legal landscape. Many of these crime figures were brought to justice not through traditional means, but by leveraging laws like the Internal Revenue Code, Hobbs Act, and RICO. These legal strategies remain foundational in prosecuting organized crime today. Defense attorneys in these high-profile cases played pivotal roles, demonstrating the importance of skilled legal counsel when facing complex criminal statutes.

 

NCS
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