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Gangsters, Mobsters & Outlaws

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If the Old West Outlaws get a lot of historic attention, a close second are the gangsters of the 1920’s Prohibition era and the 1930's Depression period. Feared and revered, these American gangsters often controlled liquor sales, gambling, and prostitution, while making popular, silk suits, diamond rings, guns, booze and broads.  


These many men, though often murderers and outright robbers, were sometimes also involved in the political, social, and economic conditions of the times. Infamous names of the era included people such as Al Capone, Vito Genovese, Dutch Schultz, Jack "Legs" Diamond, Charles "Lucky" Luciano, John Dillinger, and Bugsy Siegel.


The Depression created yet another type of outlaw, fed by both need and greed. Though not as "revered" as the 1920's gangsters, Depression era outlaws with names like Bonnie and Clyde, "Baby Face" Nelson, Ma Barker, and "Pretty Boy" Floyd, also became legends, as their deeds included some of the wildest and deadliest stories ever to hit newspaper front pages.


Much like the days of the Old West following the Civil War, these were difficult times for the vast majority of Americans and like the gunmen before them, the outlaws of the 1920s and '30s gained fame among those who dreamed of individuality and fast money. The "romance” of the lifestyle and resistance to the socially imposed rules of the times led numerous men and a few women into a criminal life that included bank robberies, illegal sales of alcohol, gambling, prostitution, and black market drugs.


St Valentine's Massacre, Chicago, Illinois

Bodies of gangsters lying on a Chicago garage floor following

 the St. Valentine's Day massacre in Chicago, Illinois.




With it came violence, spawned mostly by bitter gang rivalries in the 1920s. In those days, gangster killings were unlike those of the Old West or those of today. They were generally calculated business practices rather than personal vendettas, where one gang would line up rival gang members and shoot them down, or make a surprise attack on them, blasting or bombing until their rivals were dead. In the 1930s, the violence was more desperate as outlaws were determined to have their way at any cost.  

Though these men and women were violent criminals, like their predecessors in the days of the Old West, the public couldn’t get enough of them – craving the news stories, photographs, tales of luxurious living, and the morbid facts of violent deeds.

In the end, most of these outlaws were sent to jail, killed by rival gangsters, or killed by law enforcement, but their legends live on.


Gangsters & Outlaws



  • Edward "Eddie" J. Adams (1887-1921) - A Kansas bootlegger, car thief, and murderer, Adams was eventually captured and sentenced to life imprisonment. He escaped custody twice and was killed in a shootout with police in Wichita, Kansas on November 22, 1921. See Full Article HERE.

  • Gordon Alcorn - Involved with Verne Sankey in a kidnapping, Alcorn was sent to Leavenworth Federal Prison.

  • John William Anglin and Alfred Clarence angling  - Georgia bank robbers who were arrested in 1956 and ultimately sent to Alcatraz. They escaped in the June 1962 was never seen again. See Article HERE.

  • George "Dutch" Anderson (1879-1925) A Danish criminal, Anderson, along with Gerald Chapman, co-led a Prohibition-era gang during the late 1910s until the mid-1920s. He and his associates successfully robbed a US Mail truck of $2.4 million in cash, bonds, and jewelry. Finally captured, he was sentenced to 25 years in prison but later escaped. He was killed in a police shootout on October 31, 1925.

  • Albert Anastasia (1902-1957) - Born Umberto Anastasio, he was one of the most ruthless and feared Cosa Nostra mobsters in United States history. A founder of both the American Mafia, and Murder, Inc. during the prewar era and during most of the 1950s, Anastasia was boss of what would become the modern Gambino crime family.

  • Ashley Gang - Led by John H. Ashley, the gang terrorized Florida’s southeast coast for more than 15 years, committing crimes that ranged from murder, bank robbery, hijacking, bootlegging, to piracy on the high seas.

  • John H. Ashley (1895-1924) - Leading the Ashley Gang, which terrorized Florida’s southeast coast for more than 15 years, the gang committed crimes that ranged from murder, bank robbery, hijacking, bootlegging, to piracy on the high seas. He was killed by law enforcers on November 1, 1924.

  • Theodore "Blackie" Audett - A prisoner of Alcatraz, Audett claimed to have been a Barker-Karpis Gang, but this has been disputed by the facts. He was a jailhouse author noted for his fantastic claims about other prisoners and his own life. While in Alcatraz, he was also known to have been a snitch who was a defense witness in the 1946 Blast-Out Trial.

  • Abe Axler - A member of the Purple Gang, Axler was assassinated in November, 1933.


  • Harvey John Bailey (1887-1979) - A partner of Machine Gun Kelly, Bailey was considered one of the most successful bank robbers of the 1920's, Bailey stole over a million dollars. He was thought to have been involved in the Kansas City Union Station Massacre. He was eventually captured and spent 31 years in prison. He died at the age 91 in Joplin, Missouri. 

  • Basil Hugh "The Owl" Banghart (1900-1982) -  An underworld legend, Banghart was a machine gunner and aviator for the mob. He was eventually sentenced to prison and was released at the age of 60. He lived out the remainder of his life on a small island in Puget Sound.

  • Arthur R. "Doc" Barker (1899-1939) - Member of Barker-Karpis Gang, Barker was shot and killed while trying to escape from Alcatraz in 1939.

  • Kate "Ma" Barker (1873-1935) - An alleged member of the Barker-Karpis Gang, who committed a spree of robberies, kidnappings and other crimes between 1931 and 1935, Barker was killed in a shoot-out with police on January 16, 1935.

  • Lloyd Barkdoll - A bank robber, Barkdoll was sentenced to prison and wound up in Alcatraz, where he attempted to escape in 1941.

  • Barker-Karpis Gang (1931-1935) - Kate "Ma" Barker and her sons, Herman, Lloyd, Arthur, and Fred teamed up with Alvin Karpis and several other criminals, who terrorized the Midwest and reached the position of Public Enemy #1 on the FBI "Most Wanted List."

  • George Kelly Barnes, aka: George "Machine Gun" Kelly  (1900-1954) - A notorious Prohibition era criminal, his crimes included bootlegging, armed robbery and, most prominently, kidnapping. He spent some time in Alcatraz before dying of a heart attack at Leavenworth Federal Prison, Kansas on July 18, 1954. 

  • Barrow Gang (1932-1934) - Well known outlaws, robbers, and criminals who traveled the Midwest and Texas during the Great Depression.

  • Bennie Iva "Blanche" Caldwell Barrow (1911-1988) - The wife of Marvin "Buck" Barrow and a member of the Barrow Gang.

  • Clyde Barrow (1909-1934) - Half of the infamous Bonnie and Clyde pair, these two were criminals who, with the Barrow Gang, traveled and robbed numerous locations in the Central United States during the Great Depression.

  • Marvin "Buck" Barrow (1903-1933) - A member of the Barrow Gang. He was the older brother of the gang's leader, Clyde Barrow. He and his wife Blanche were wounded in a gun battle with police four months after they joined up with Bonnie and Clyde. Marvin died of his wounds.

  • Albert Bates (??-1948) - A partner of Machine Gun Kelly, Bates served time in Alcatraz.

  • Edward "Eddie" Wilheim Bentz (1895-1936) - Partnered with such names as Machine Gun Kelly and  Baby Face Nelson, Bentz was one the shrewdest, most resourceful, intelligent and dangerous bank robbers of the Depression era.

  • Joe Bergl (1901-1950) - A mechanic for Al Capone, he supplied Capone with custom-made vehicles designed for protection and evasion purposes that included armor plating, smokescreens, and oil slicks. 

  • Abe Bernstein (1892-1968) - A Detroit, Michigan gangster and a leader of the infamous Prohibition-era Purple Gang. He began branching out to other major cities during the mid-1920s, eventually becoming an associate of New York mobsters and a partner in several syndicate gambling casinos in Miami, Florida. He died on March 7, 1968.

  • Raymond Bernstein - a member of the Purple Gang, Bernstein was sentenced to life in prison in 1931 for murder.

  • George Birdwell (1894-1932) - A partner and friend of Oklahoma outlaw Pretty Boy Floyd, Birdwell and Floyd robbed a number of banks in Oklahoma, including two banks on one day on December 12, 1931 in Castle and Paden, Oklahoma. Alone, Birdwell attempted to hold up the bank in the African-American community of Boley, Oklahoma in November, 1932 and was shot from within the vault by a citizen.

  • James Boarman - A bank robber, Boarman was sent to Alcatraz and during a 1943 escape attempt was killed.

  • Joe Bowers (??-1936) - Sent to Alcatraz for robbery, Bowers was the first man to attempt to escape Alcatraz. He was killed in the attempt.

  • Ford Bradshaw (1908-1934) - One time leader of Cookson Hills Gang and partner of Wilber Underhill and Charlie Cotner. He was suspected of numerous bank robberies in Oklahoma, Kansas, Arkansas, and Nebraska, and suspected of four murders. He was killed by Constable Bill Harper at Arkoma, Oklahoma in March, 1934.

  • Tom "Skeet" Bradshaw - Brother of notorious bank robber and murderer Ford Bradshaw and member of the Cookson Hills Gang. Suspect in bank robberies in Vian, Oklahoma and Chetopa, Kansas. Convicted of attempted murder and bootlegging in 1934.

  • Al Brady (1911-1937) - Wanted for murder and robbery in the Midwest, Brady was killed by FBI men in Bangor, Maine in October, 1937. 

  • Harold Brest - A Pennsylvania bank robber, Brest was sent to Alcatraz and participated in  Participant in Floyd Hamilton's 1943 escape attempt.

  • Harry Brunette (1911-??) - Kidnapper and bank robber. In 1936 he was involved in a gunfight with the FBI and arrested.

  • Fred "Killer" Burke (1885-1940) - An armed robber, contract killer, and primary suspect in the St. Valentine's Day Massacre. Once named America's most wanted man, he was eventually imprisoned and died there of heart disease.


Continued Next Page


Speakeasy of the Prohibition Era

Speakeasy of the Prohibition era


Also See:


The Long History of Alcatraz Island

Ghosts of Alcatraz

The Kansas City Massacre

Speakeasies of the Prohibition Era

The Great Depression


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