Kelley Bahena

Written by Kelley Bahena

Modified & Updated: 23 Sep 2024

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Source: Youtube.com

Legs Diamond, also known as Jack Diamond, was one of the most notorious gangsters during the Prohibition era. Born in Philadelphia in 1897, he quickly rose through the ranks of organized crime. Why was he called "Legs"? The nickname came from his ability to escape dangerous situations, often fleeing on foot. Diamond's life was a whirlwind of bootlegging, violence, and multiple assassination attempts. He was known for his flashy lifestyle, which included expensive suits, fast cars, and glamorous women. Despite his criminal activities, Diamond had a certain charisma that made him a legend. His story is filled with daring escapes, brutal confrontations, and a relentless pursuit of power.

Key Takeaways:

  • Legs Diamond, a notorious gangster known for his daring escapes and lavish lifestyle, rose to power in the criminal underworld during the Prohibition era, but his luck eventually ran out, leading to his dramatic downfall and unsolved murder.
  • Despite his criminal activities, Legs Diamond's life and death left a lasting impact on popular culture, inspiring films, a Broadway musical, and numerous books and documentaries, adding to his mystique and notoriety.
Table of Contents

Who Was Legs Diamond?

Legs Diamond, a notorious gangster from the Prohibition era, lived a life filled with crime, intrigue, and violence. His real name was Jack Diamond, but his nickname "Legs" came from his ability to escape dangerous situations.

  1. Jack Diamond was born on July 10, 1897, in Philadelphia, Pennsylvania.
  2. He earned the nickname "Legs" due to his knack for escaping law enforcement.
  3. Diamond was involved in bootlegging during Prohibition, smuggling alcohol into the United States.
  4. He was known for his flamboyant lifestyle, often seen in expensive suits and driving luxury cars.
  5. Diamond had a reputation for being charming yet ruthless, making him both feared and admired.

Early Life and Criminal Beginnings

Jack Diamond's early life set the stage for his future in organized crime. From a young age, he was involved in petty crimes, which eventually escalated.

  1. Diamond's family immigrated from Ireland to the United States.
  2. He dropped out of school at a young age and joined a street gang.
  3. Diamond was first arrested at the age of 17 for burglary.
  4. He served in the U.S. Army during World War I but was dishonorably discharged.
  5. After the war, Diamond moved to New York City, where he became involved in more serious criminal activities.

Rise to Power

Legs Diamond's rise to power in the criminal underworld was marked by violence and strategic alliances. He quickly became a key player in the bootlegging industry.

  1. Diamond worked for Arnold Rothstein, a major figure in organized crime.
  2. He established his own bootlegging operation, smuggling alcohol from Canada.
  3. Diamond's gang was known for its brutality, often using violence to eliminate rivals.
  4. He survived multiple assassination attempts, earning a reputation for being nearly invincible.
  5. Diamond was involved in the infamous Manhattan Beer Wars, a violent conflict between rival bootlegging gangs.

Personal Life and Relationships

Despite his criminal activities, Legs Diamond had a personal life filled with drama and scandal. His relationships often made headlines.

  1. Diamond married Alice Kenny in 1920.
  2. He had a long-term affair with Marion "Kiki" Roberts, a showgirl.
  3. Diamond's wife, Alice, was known to be loyal despite his infidelities.
  4. He was often seen in the company of celebrities and socialites.
  5. Diamond's lavish lifestyle included parties at his luxurious apartment in New York City.

Legal Troubles and Imprisonment

Legs Diamond's criminal activities eventually caught up with him, leading to numerous legal troubles and stints in prison.

  1. Diamond was arrested multiple times for bootlegging and other crimes.
  2. He was convicted of kidnapping in 1929 but managed to escape from custody.
  3. Diamond served time in Sing Sing prison but continued to run his operations from behind bars.
  4. He was acquitted of murder charges in 1931, further enhancing his reputation.
  5. Diamond's legal battles drained his financial resources, leading to increased tensions within his gang.

The Downfall of Legs Diamond

Despite his many escapes from death and the law, Legs Diamond's luck eventually ran out. His downfall was as dramatic as his rise to power.

  1. Diamond's gang began to disintegrate due to internal conflicts.
  2. He was shot multiple times in October 1930 but survived.
  3. Diamond's enemies included both rival gangsters and law enforcement.
  4. On December 18, 1931, Diamond was ambushed and killed in Albany, New York.
  5. His murder remains unsolved, with many theories about who was responsible.

Legacy and Cultural Impact

Legs Diamond's life and death left a lasting impact on popular culture. His story has been retold in various forms of media.

  1. Diamond's life inspired the 1959 film "The Rise and Fall of Legs Diamond."
  2. He was portrayed by actor Ray Danton in the film.
  3. Diamond's story was also adapted into a Broadway musical in 1988.
  4. The musical, titled "Legs Diamond," starred Peter Allen.
  5. Diamond's life has been the subject of numerous books and documentaries.

Interesting Tidbits

Beyond the well-known facts, there are several lesser-known tidbits about Legs Diamond that add to his mystique.

  1. Diamond was known to tip generously at restaurants and clubs.
  2. He had a pet monkey named Jocko, which he often brought to parties.
  3. Diamond was a fan of boxing and frequently attended matches.
  4. He once escaped from a hospital after being shot, despite his severe injuries.
  5. Diamond's final resting place is in Mount Olivet Cemetery in Queens, New York.

The Legacy of Legs Diamond

Legs Diamond, a name that still echoes through the annals of crime history, left an indelible mark on the Prohibition era. Known for his cunning, charm, and numerous brushes with death, Diamond's life was a rollercoaster of crime, luxury, and violence. His ability to evade the law and survive multiple assassination attempts earned him a legendary status among gangsters. However, his luck ran out in 1931 when he was finally gunned down in Albany, New York. Despite his criminal activities, Diamond's story continues to fascinate, offering a glimpse into the tumultuous world of early 20th-century organized crime. His life serves as a reminder of the era's lawlessness and the lengths individuals would go for power and wealth. Legs Diamond remains a captivating figure, embodying the perilous allure of the gangster lifestyle.

Frequently Asked Questions

Who was Legs Diamond?
Legs Diamond, also known as Jack Diamond, was a notorious gangster during Prohibition in the United States. He earned his nickname due to his ability to evade capture and escape from his enemies, seemingly dancing away from danger with his "legs."
What made Legs Diamond famous?
His fame came from his reputation as an untouchable bootlegger, his numerous escapes from death, and his flamboyant lifestyle. Diamond's ability to survive multiple assassination attempts added to his legend, making headlines across the country.
How did Legs Diamond die?
Despite surviving numerous attempts on his life, Legs Diamond's luck ran out on December 18, 1931. He was shot and killed in a cheap Albany, New York, boarding house. The murder remains officially unsolved, adding a layer of mystery to his story.
Was Legs Diamond involved in any other criminal activities?
Yes, besides bootlegging, Diamond was involved in a variety of criminal activities, including armed robbery, kidnapping, and narcotics. His criminal empire extended beyond alcohol, showcasing his versatility in the underworld.
Did Legs Diamond have any rivals?
Absolutely, his life was marked by constant battles with rival gangsters. Notably, he feuded with Dutch Schultz and other prominent figures of the organized crime world. These rivalries often turned violent, contributing to the era's lawlessness.
Has Legs Diamond been portrayed in movies or books?
Indeed, Legs Diamond's life has inspired numerous books, movies, and even a Broadway musical. His character often appears as a symbol of the Roaring Twenties and the Prohibition era's excesses and dangers.
What is Legs Diamond's legacy today?
Today, Legs Diamond is remembered as one of the most charismatic and elusive gangsters of the Prohibition era. His story is a testament to the tumultuous times of 1920s and 1930s America, reflecting the complex interplay between crime, law enforcement, and society during that period.

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