The Most Famous Bootlegger, Ranked

Choose the bootlegger you think is the most famous!

Author: Gregor Krambs
Updated on Apr 24, 2024 08:10
In the roaring twenties, illegal distilleries and secret speakeasies ruled the night. Knowing the key players in this risky business provided not just entertainment, but essential knowledge on where to find the best moonshine - often under the radar of the law. Tracking the most famed figures within this clandestine world was a topic of much debate and interest. Today, casting your vote on who topped the bootlegging charts injects a playful, historical inquiry into these shadowy figures from the past. By voting, you not only engage with history but also help determine who was the cleverest, or perhaps the most notorious, among them. Your participation shapes a collective remembrance and offers a dynamic interaction with our spirited past.

Who Is the Most Famous Bootlegger?

  1. 1
    55
    votes
    Known as one of the most notorious bootleggers during the Prohibition era, Capone built a criminal empire through illegal alcohol sales.
    Al Capone in other rankings
  2. 2
    25
    votes
    A lawyer turned bootlegger who became known as the "King of the Bootleggers," Remus smuggled and sold alcohol during the Prohibition era.
  3. 3
    22
    votes
    Known for his high-quality "bootleg" alcohol, McCoy gained fame for his smuggling operation that supplied alcohol to wealthy clients during the Prohibition era.
  4. 4
    19
    votes
    A former police officer turned bootlegger, Olmstead controlled a large portion of the illegal alcohol trade in Seattle during the Prohibition era.
  5. 5
    14
    votes
    A well-known mobster during the Prohibition era, Costello was involved in various criminal activities, including bootlegging.
    Frank Costello in other rankings
  6. 6
    11
    votes
    Joseph Kennedy Sr.
    Photographer: Larry Gordon · Public domain
    The father of President John F. Kennedy, Joseph Kennedy Sr. was involved in bootlegging during the Prohibition era, which helped him amass a fortune.
  7. 7
    6
    votes
    Dutch Schultz
    New York Police Department · Public domain
    A notorious gangster and bootlegger during the Prohibition era, Schultz controlled a large portion of the illegal alcohol trade in New York City.
  8. 8
    11
    votes
    Arnold Rothstein
    Staff Photographer · Public domain
    A well-known gambler and bootlegger during the Prohibition era, Rothstein was involved in various criminal activities, including fixing the 1919 World Series.
  9. 9
    9
    votes
    Johnny Torrio
    Unknown authorUnknown author · Public domain
    A mentor to Al Capone, Torrio was a prominent bootlegger during the Prohibition era and helped build Capone's criminal empire.
  10. 10
    10
    votes
    Bugsy Siegel
    New York Police Department · Public domain
    Known as a gangster and bootlegger during the Prohibition era, Siegel later became involved in the development of Las Vegas.
    Bugsy Siegel in other rankings

Missing your favorite bootlegger?

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About this ranking

This is a community-based ranking of the most famous bootlegger. We do our best to provide fair voting, but it is not intended to be exhaustive. So if you notice something or Bootlegger is missing, feel free to help improve the ranking!

Statistics

  • 3055 views
  • 174 votes
  • 10 ranked items

Voting Rules

A participant may cast an up or down vote for each Bootlegger once every 24 hours. The rank of each Bootlegger is then calculated from the weighted sum of all up and down votes.

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More information on most famous bootlegger

Bootlegging was a widespread practice during the Prohibition era in the United States from 1920 to 1933. It involves the illegal production, distribution, and sale of alcohol, which was prohibited during this period. The most famous bootleggers in history were notorious for their ingenuity and cunning in evading the law and making huge profits. Names like Al Capone, George Remus, and the infamous Canadian gangster Rocco Perri are still remembered today for their role in the illegal alcohol trade. These bootleggers were often involved in organized crime, and they used their wealth and power to influence politics and law enforcement. Despite the dangers and risks involved, bootlegging remained a lucrative business during Prohibition, and its legacy still lives on today in popular culture and folklore.

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